JPH10139778A - Dioxane derivative having fluoroalkyl group, liquid crystal composition and liquid crystal display element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new liquid crystalline compound consisting of a specific dioxane derivative having a fluoroalkyl group, having a large Δεand a high specific resistivity, excellent in compatibility with a conventional liquid crystalline compound and suitable for a low voltage driven TFT type liquid crystal display element. SOLUTION: This dioxane derivative having a fluoroalkyl group is expressed by formula I [(n0) is 2-10; (n1), (n2) are each 0-2; (n3), (n4) are each 0, 1; (n3)>=(n4); (n1+n2+n3+n4)<=2; Q1 , Q2 are each H, F or Cl; Za, Zb, Zc are each single bond, CH2 CH2 tetramethylene, COO or CF2 O; ring A1, ring A2 are each a group of formula II to formula IV, etc.; Y is H, a halogen or a 1-5C halogenated alkyl and in the case that the halogen is F, (n1)=(n2)=(n4)=0, (n3)=1, Zb is the single bond, also the ring A1 is not a group expressed by formula III, and the halogenated alkyl is allowed to be substituted by O, S at one or more methylene groups not adjacent each other therein], has liquid crystalline properties and is useful as a component, etc., of a liquid crystalline composition for a TFT type liquid crystal displaying element, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal compound and a liquid crystal composition, and more particularly to a liquid crystal composition, particularly a dioxane derivative having a fluoroalkyl group, which is a liquid crystal compound suitable as a component of a liquid crystal composition for TFT. The present invention also relates to a liquid crystal composition containing the same and a liquid crystal display device formed using the liquid crystal composition.

[0002]

2. Description of the Related Art A liquid crystal display device utilizes the optical anisotropy and dielectric anisotropy of a liquid crystal material. Depending on the display method, a TN type (twisted nematic type) or a DS type (dynamic scattering type) is used. , G. H type (guest / host type), DA
The liquid crystal material is classified into various types such as a P type (alignment phase change type) and an STN type (super twisted nematic type), and the properties of the liquid crystal material suitable for each use are different. In recent years, particularly, a liquid crystal display element having higher display quality has been demanded, and in order to meet the demand, demand for an active matrix display element represented by a TFT type (thin film transistor type) has been increasing. The liquid crystal material used in any display element needs to be stable to moisture, air, heat, light, etc., exhibits a liquid crystal phase in a temperature range as wide as possible around room temperature, has low viscosity, and has a low viscosity. Good compatibility with liquid crystal compounds (hereinafter, a compound having a liquid crystal phase and a compound which does not impair the liquid crystal phase even when mixed with other liquid crystals) and a liquid crystal composition, and has a large dielectric anisotropy value (Δε) and the optimal optical (refractive index) anisotropy value (Δ
n) and exhibit a high specific resistance value. However, at present, no single compound satisfies all of these conditions, and a liquid crystal composition obtained by mixing several kinds of liquid crystal compounds is used at present.

In recent years, TFT-type liquid crystal display elements have been particularly required to have low-voltage drivability.
A liquid crystal compound or a liquid crystal composition having a larger Δε than a conventional liquid crystal material used for a T-type liquid crystal display element has been required. For this reason, liquid crystal materials having a large Δε while exhibiting a high specific resistance have been actively developed.
Conventionally, a fluorine-based liquid crystal material having a high specific resistance, for example, a compound represented by the following formula (10) is generally known (Japanese Patent Publication No. 01-04496).

[0004]

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The compound (10) has a higher specific resistance than the liquid crystalline compound having a cyano group, and thus has a high T value.
Although it is used as a component of a liquid crystal composition for FT, its extrapolation Δε is as small as 8.7,
It cannot be used as a liquid crystal material for low voltage driving represented by V driving. The above-mentioned extrapolation Δε is calculated by dissolving the compound (10) in a mother liquid crystal having a nematic phase and calculating the Δε of the composition thus obtained, the Δε of the mother liquid crystal, and the compound mixing ratio in the composition. However, it substantially reflects Δε of the compound (10) (in the following description, Δε for the compound is used in the same meaning as described above). A trifluorophenyl derivative represented by the following formula (11) is known as a compound having ΔΔ larger than that of the compound (10) (Japanese Patent Application Laid-Open No.
233626).

[0006]

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The compound (11) has a Δε of 11.7.
Shows a value larger than that of the compound (10), but is not a material that can meet the demand for low voltage in the market for the same reason as described above. Further, a trifluoromethylphenyl derivative represented by the formula (12) and a trifluoromethoxyphenyl derivative represented by the formula (13) are also known (Japanese Unexamined Patent Publication No.
4-506361).

[0008]

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However, these compounds also have an insufficient Δε (for example, Δε of the compound (13) is 8.7 (IDY (Television Technical Report) 95)), and for the same reason as described above, the market potential is low. It cannot meet the demand for low voltage. In the above compound (13), the following formula (1) wherein two fluorine atoms are substituted at the lateral position of the central benzene ring:
The tricyclic compound shown in 4) is also known (IDY (Television Technical Report) 95).

[0010]

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This compound (14) has a Δε of 13.
At 0, 4.3 is larger than that of the compound (13), but it is not a material that can meet the demand for low voltage in the market for the same reason as described above. A dioxane derivative represented by the following formula (15) is also known as a compound having a larger Δε. (JP-A-02-233626).

[0012]

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According to the measurement by the present inventors, this compound (15) has a large Δε of about 15, but by using this compound, the driving voltage of the TFT type liquid crystal display element can be reduced to a required level. It is still inadequate for lowering, and the appearance of compounds having even larger Δε is expected. As a dioxane derivative similar to the compound (15), a dioxane derivative having a fluoroalkyl group as shown in the formula (16) is also known (US Pat.
Pat. No. 5494606), and the Δε of this compound does not exceed that of the compound (15).

[0014]

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[0015]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned drawbacks of the prior art, to provide an extremely large Δε, a high specific resistance, electrical and chemical stability, and a conventional liquid crystal. Good compatibility with water-soluble compounds, especially TF
A liquid crystalline compound suitable for driving a T-type liquid crystal display element at a low voltage;
It is an object of the present invention to provide a liquid crystal composition containing the same and a liquid crystal display device constituted by using the same.

[0016]

Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and as a result, have a combination of a fluoroalkyl group and a 1,3-dioxane-2,5-diyl group in a molecule; And a covalent bond at the 2-position of the dioxane ring, -C
A dioxane derivative having a structure in which a benzene ring, a cyclohexane ring or a silinane ring which may be substituted with a fluorine or chlorine atom via H ₂ CH ₂ — or —CH ₂ CH ₂ CH ₂ CH ₂ — has a large Δε. Completed the invention by finding that it has good compatibility with existing liquid crystal compounds and has a high specific resistance value, and is most suitable as a liquid crystal material for TFT low voltage driving represented by 2.5V driving. Reached.

That is, the configuration of the present invention is as follows. (1) General formula (1)

[0018]

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Wherein n0 is an integer of 2 to 10,
1 and n2 are each independently an integer of 0 to 2,
n3 and n4 are each independently 0 or 1, but n3 ≧ n4 and n1 + n3 + n4 ≦ 2, and Q ₁
And Q ₂ each independently represent a hydrogen atom, a fluorine atom or a chlorine atom, and Za, Zb and Zc each independently represent a single bond, -CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂
CH ₂ —, —COO— or —CF ₂ O— represents a ring A1
And ring A2 are each independently of the formulas (a) to (i)

[0020]

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And Y represents a hydrogen atom, a halogen atom or a halogenated alkyl group having 1 to 5 carbon atoms. When the halogen atom is a fluorine atom, n1 = n2 = n4 = 0, n3 = 1, Zb = single bond, ring A1 is not a group represented by formula (b), and the halogenated alkyl group is one or more non-adjacent methylene groups in the group. The groups may be replaced by oxygen or sulfur atoms. Each element constituting the compound may include those selected from isotopes thereof. ). (2) The dioxane derivative according to (1), wherein n1 = n3 = n4 = 0. (3) The dioxane derivative according to (1), wherein n1 + n3 + n4 = 1. (4) The dioxane derivative according to (1), wherein n1 + n3 + n4 = 2. (5) The dioxane derivative according to (1), wherein n2 ≠ 0 and ring A1 is a group represented by formula (a). (6) The dioxane derivative according to (1), wherein n2 = 0 and n3 = 1. (7) n2 = 0, n3 = 1 and the ring A1 is represented by the formula (c)-
The dioxane derivative according to (1), which is a group selected from the group consisting of (g).

(8) A liquid crystal composition comprising at least one dioxane derivative according to any one of (1) to (7). (9) As a first component, at least one dioxane derivative according to any of (1) to (7) is contained, and as a second component, general formulas (2), (3) and (4)

[0023]

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(In each formula, R ₃ , Y ₁ , L ₁ , L ₂ , Z ₁ and Z ₂ may be the same or different among the formulas, and R ₃ is an alkyl group having 1 to 10 carbon atoms. Wherein, in the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or -CH = CH-, and any hydrogen atom may be substituted with a fluorine atom .Y
₁ 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 OCF ₂
CFHCF ₃ , L ₁ and L ₂ are each independently a hydrogen atom or a fluorine atom, Z ₁ and Z ₂ are each independently —CH _{2
CH 2 -, - CH 2 CH} 2 CH 2 CH 2 -, - COO -, -
CF ₂ O—, —OCF ₂ —, —CH ＝ CH— or a single bond is shown. Ring B is trans-1,4-cyclohexylene,
1,4-dioxane-2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, ring C may be trans-1,4-cyclohexylene or a hydrogen atom in which a hydrogen atom is substituted by a fluorine atom. Shows good 1,4-phenylene. In the compounds of each formula, each element constituting them may include those selected from their isotopes. At least one compound selected from the group consisting of
A liquid crystal composition characterized by containing various types. (10) As the first component, at least one dioxane derivative according to any one of (1) to (7) is contained, and as the second component, the general formula (5) and / or (6)

[0025]

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(In each formula, R ₄ and R ₅ each independently represent an alkyl group having 1 to 10 carbon atoms.
One or more non-adjacent methylene groups is an oxygen atom or-
CH = CH- may be substituted, and any hydrogen atom may be substituted by a fluorine atom. Y ₂ is a —CN group or —C≡C—CN; ring E is trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl , Ring G is trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl whose hydrogen atom may be substituted by fluorine atom, ring H is trans-1,4-cyclohexylene or 1, 4-phenylene, Z ₃ is —CH ₂ CH ₂ —, —COO— or a single bond,
L ₃ , L ₄ and L ₅ each independently represent a hydrogen atom or a fluorine atom, and b, c and d each independently represent 0 or 1. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A) a liquid crystal composition comprising at least one compound selected from the group consisting of: (11) As a first component, at least one dioxane derivative according to any of (1) to (7) is contained, and as a second component, general formulas (2), (3) and (4)

[0027]

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(In each formula, R ₃ , Y ₁ , L ₁ , L ₂ , Z ₁ and Z ₂ may be the same or different among the formulas, and R ₃ is an alkyl group having 1 to 10 carbon atoms. Wherein, in the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or -CH = CH-, and any hydrogen atom may be substituted with a fluorine atom .Y
₁ 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 OCF ₂
CFHCF ₃ , L ₁ and L ₂ are each independently a hydrogen atom or a fluorine atom, Z ₁ and Z ₂ are each independently —CH _{2
CH 2 -, - CH 2 CH} 2 CH 2 CH 2 -, - COO -, -
CF ₂ O—, —OCF ₂ —, —CH ＝ CH— or a single bond is shown. Ring B is trans-1,4-cyclohexylene,
1,4-dioxane-2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, ring C may be trans-1,4-cyclohexylene or a hydrogen atom in which a hydrogen atom is substituted by a fluorine atom. Shows good 1,4-phenylene. In the compounds of each formula, each element constituting them may include those selected from their isotopes. At least one compound selected from the group consisting of
Contained as a third component, represented by general formulas (7), (8) and (9)

[0029]

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(In each formula, R ₆ , R ₇ , I, J and K may be the same or different among the formulas, and R ₆ and R ₇ are each independently an alkyl having 1 to 10 carbon atoms. A group in which, in the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or -CH = CH-, and any hydrogen atom may be substituted with a fluorine atom. I, J and K are each independently trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or a hydrogen atom in which a hydrogen atom may be replaced by a fluorine atom 1,
4-phenylene, Z ₄ and Z ₅ are each independently -C≡
C -, - COO -, - CH 2 CH 2 -, - shows a CH = CH- or a single bond. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A liquid crystal composition comprising at least one compound selected from the group consisting of:

(12) As the first component, at least one dioxane derivative according to any one of (1) to (7) is contained, and as the second component, the general formula (5) and / or (6) At least one compound selected from
Contains, as the third component, the general formula (7),
A liquid crystal composition comprising at least one compound selected from the group consisting of (8) and (9). (13) The first component contains at least one dioxane derivative according to any one of (1) to (7), and as a part of the second component, the general formulas (2), (3) and (4). And at least one compound selected from the general formulas (5) and / or (6) as another part of the second component. A liquid crystal composition comprising, as three components, at least one compound selected from the group consisting of the general formulas (7), (8) and (9). (14) The liquid crystal composition according to any one of (8) to (13), further comprising an optically active compound. (15) A liquid crystal display device comprising the liquid crystal composition according to any one of (8) to (14).

[0032]

BEST MODE FOR CARRYING OUT THE INVENTION The liquid crystalline compound represented by the general formula (1) of the present invention, ie, a dioxane derivative having a fluoroalkyl group, has a fluoroalkyl group and 1,
A combined 3-dioxane-2,5-diyl group, and covalently attached to the 2-position of the dioxane ring, -CH ₂ CH ₂ - or -CH ₂ CH ₂ CH ₂ CH ₂ - via a fluorine or chlorine atom Has a structure in which a core portion is composed of 2 to 4 rings including a dioxane ring to which a benzene ring, a cyclohexane ring or a silinane ring which may be substituted are bonded. (For example, Δε of compound No. 52 described later is 19), and has good compatibility with existing liquid crystal compounds and shows a high specific resistance. Therefore, when such a liquid crystal compound of the present invention is used as a component of a liquid crystal composition, a liquid crystal composition particularly useful for lowering the voltage of a TFT type liquid crystal display device can be provided.

In the above formula (1), n0 is an integer relating to the determination of the chain length (the number of carbon atoms) of the fluoroalkyl group. Is suitable, preferably 2 to 7, and more preferably 2 to 5. Za, Zb and Zc of the linking group are as described above, and each is independently a single bond, -CH
₂ CH ₂ —, —CH ₂ CH ₂ CH ₂ CH ₂ —, —COO— or —CF ₂ O— is shown. n2 is an integer for determining the chain length (the number of carbon atoms) of the linking group provided between the 2-position of the dioxane ring and the other ring, and 0 to 2 is suitable. Its value is 0, 1 or 2
Depending on the case where each linking group is a single bond, -CH ₂
CH ₂ — or —CH ₂ CH ₂ CH ₂ CH ₂ —. Among the above-mentioned linking groups, a single bond has a relatively high clearing point, a compound having a relatively low viscosity and being chemically and electrically stable,
CH ₂ CH ₂ — and —CH ₂ CH ₂ CH ₂ CH ₂ — are compounds that have excellent compatibility with other liquid crystal compounds or liquid crystal compositions and are chemically and electrically stable, and —COO— is highly transparent. A compound having a point and exhibiting a large Δε is also referred to as —CF ₂
O- is low in viscosity, has a relatively large [Delta] [epsilon], and can provide chemically and electrically stable compounds, respectively.

Further, n1 is an integer of 0 to 2, and n3 and n4 are each independently 0 or 1, but n3 ≧ n4 and n1 + n3 + n4 ≦ 2. As a specific example of a combination satisfying such conditions, n1, n3 and n4 are all 0, n1 and n4 are both 0 and n3 is 1, n1 is 1 and n3 and n4 are both 0, and n1 + n3 + n4 is 2 (n1 and n3
Are 1 and n4 is 0, n1 is 2 and both n3 and n4 are 0)
Can be mentioned. Compounds sequentially corresponding to these combinations are represented by the following formulas (1-a) and (1-
b) to (1-d), (1-e) and (1-f) to (1)
-H).

[0035]

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(Where n0, n2, Za, Zb, Z
c, ring A1, ring A2, Q ₁ , Q ₂ and Y have the same meaning as described above, and n5 is 1 or 2. Of the above compounds, those represented by the formula (1-a) have a low viscosity, have excellent compatibility with other liquid crystal compounds or liquid crystal compositions, and have a large Δε; ) Has a large Δn and a large Δε, and the expression (1-
Compounds represented by c), (1-d) and formula (1-e) where n2 ≠ 0 have a large Δε, a relatively low viscosity and a high specific resistance. . Those in which n2 = 0 in the above formula (1-e) have a relatively high clearing point, and have the above formulas (1-b) to (1-d).
Is less viscous than that represented by Equation (1-f)
The 4-ring compound represented by-(1-h) has a high clearing point and a large Δε.

The terminal substituent Y represents a hydrogen atom, a halogen atom or a halogenated alkyl group having 1 to 5 carbon atoms as described above, and the halogenated alkyl group is one or more non-contiguous groups in the group. The methylene group may be replaced by an oxygen atom or a sulfur atom. Of these, compounds having a halogen atom as a fluorine atom have a relatively large Δ
It has ε, has low viscosity, and has excellent compatibility with other liquid crystal compounds or liquid crystal compositions. Further, a compound in which the halogenated alkyl group is CF ₃ has a very large Δε, and a compound in which OCF ₃ is also low in viscosity. The halogen atom is a chlorine atom, and the halogenated alkyl group in which one or more non-adjacent methylene groups in the group are replaced by an oxygen atom is OCF ₂ CF ₂ H or OCF ₂ CFHCF ₃ Is a compound having a large Δn and a high clearing point, and a compound replaced by the same oxygen atom as OCH ₂ CF ₂ H or OCH ₂ CF ₃ has a high clearing point and a relatively low viscosity. . Preferable examples of the halogenated alkyl group or the halogenated alkyl group in which one or more non-adjacent methylene groups in the group are replaced with an oxygen atom further include a difluoromethyl group, a difluorochloromethyl group, , 2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethoxy, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, difluoromethoxy,
Examples include a difluorochloromethoxy group, a pentafluoroethoxy group and a heptafluoropropoxy group.

The ring A1 and the ring A2 each independently represent a group selected from the group consisting of formulas (a) to (i) as described above. A fluorine or chlorine atom may be introduced as a substituent. The introduction of these fluorine atoms or chlorine atoms gives a compound having a large Δε as the number thereof increases, and conversely, a compound having a low viscosity and a high clearing point as the number of hydrogen atoms increases as the number thereof decreases. . By the way, comparing the groups represented by the formulas (b), (c) and (e), (e) shows the largest Δε, and (b) gives the compound with the lowest viscosity and high clearing point. It is known. In addition, the group of the silinane ring represented by the formula (h) or (i) can give a compound having excellent compatibility with other liquid crystal compounds and liquid crystal compositions at a low temperature.

As described above, all of the compounds of the present invention have a combination of a fluoroalkyl group and a dioxane ring. Among them, a covalent bond at the 2-position of the dioxane ring, —CH ₂ CH ₂ — or —CH _{2 A} benzene ring, a cyclohexane ring or a silinane ring, which may be substituted with a fluorine or chlorine atom via ₂ CH ₂ CH ₂ CH ₂ —, wherein the core portion is composed of 2 to 4 rings including a dioxane ring. Are preferred in that they have a specifically large Δε. Among the benzene rings which may be substituted by the fluorine or chlorine atom, the 3-fluoro-1,4-phenylene group particularly has a relatively large Δε, exhibits a high liquid crystal phase temperature range and low viscosity, and is excellent. Compounds having high compatibility,
-Difluorophenylene groups can give compounds which have a very large Δε and show very good compatibility.

The liquid crystalline compound represented by the general formula (1) of the present invention may include those in which each element in the formula is selected from their isotopes. That is, there is no particular change in the liquid crystal characteristics as compared with the case where the isotope is not included even when the isotope is included, and the same effect can be obtained.

The compound of the present invention is particularly suitable as a component of a liquid crystal composition for a TFT, but may be used for other purposes such as a TN, a guest-host mode, a polymer-dispersed liquid crystal display device, Compounds for liquid crystal composition for selective scattering mode, STN, in-plane switching, OCB mode or R-OCB mode, and compounds for ferroelectric liquid crystal and antiferroelectric liquid crystal Also suitable as.

The liquid crystal composition provided by the present invention comprises at least one liquid crystal compound represented by the general formula (1) as a first component. Its content is
It is necessary that the content be 0.1 to 99.9% by weight based on the weight of the liquid crystal composition in order to exhibit excellent characteristics, preferably 1 to 50% by weight, more preferably 3 to 20% by weight.
It is. The liquid crystal composition of the present invention may include only the above-mentioned first component. In addition to this, at least one component selected from the group consisting of the general formulas (2), (3) and (4) referred to above as the second component. Types of compounds (hereinafter referred to as the second component A)
And a mixture of at least one compound selected from the group consisting of the general formulas (5) and / or (6) (hereinafter, referred to as a second component B),
The third component is preferably a mixture of at least one compound selected from the group consisting of the general formulas (7), (8) and (9). Further, as other components, an optically active compound or a threshold is used. Known compounds can also be mixed for the purpose of adjusting the value voltage, liquid crystal phase temperature range, Δε, Δn, viscosity and the like.

Among the above-mentioned component A, preferred examples of the compounds contained in the general formula (2) include the following formulas (2-1) to (2-)
9), Formulas (3-1) to (3-69) as preferred examples of the compound included in the general formula (3), and Formulas (4-1) to (3-69) as preferred examples of the compound included in the general formula (4) 4-24).

[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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(In each formula, R ₃ and Y ₁ have the same meanings as described above. Further, each element constituting the compound of each formula may include those selected from their isotopes.) Are represented by the general formulas (2) to (4):
When preparing a liquid crystal composition for a TFT that requires high reliability, such as a positive ε, excellent thermal stability and chemical stability, and a high voltage holding ratio (high specific resistance). It is an indispensable compound. The amount of the compound used is T
When preparing a liquid crystal composition for FT, the range of 1 to 99% by weight relative to the total weight of the liquid crystal composition is suitable, preferably 10 to 97% by weight, more preferably 40 to 95% by weight.
It is. In that case, the compounds represented by the formulas (7) to (9) may be contained.

The compounds represented by the above general formulas (2) to (4) can also be used for preparing a liquid crystal composition for an STN display system or a TN display system. Next, among the second component B, preferred examples of the compound included in the general formula (5) include the following formulas (5-1) to (5-40) and the preferred examples of the compound included in the general formula (6). Examples include compounds represented by formulas (6-1) to (6-3).

[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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(In each formula, R ₄ , R ₅ and Y ₂ have the same meanings as described above. In addition, each element constituting the compound of each formula is
It may include those selected from these isotopes. The compounds represented by the general formulas (5) and (6) have a large Δε and a large value, and are particularly used for the purpose of reducing the threshold voltage of the liquid crystal composition. It is also used for the purpose of adjusting the Δn, increasing the clearing point, expanding the nematic range of the liquid crystal composition, and improving the steepness of the threshold voltage of the liquid crystal composition for STN and TN display systems. This is an indispensable compound especially when preparing a liquid crystal composition for an STN display mode or a TN display mode. This compound can decrease the threshold voltage of the liquid crystal composition as the amount of the compound is increased, but increases the viscosity. 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 for low voltage driving. Under such circumstances, when preparing a liquid crystal composition for the STN display mode or the TN display mode, the above-mentioned usage amount is 0.1 to 99.99% based on the total weight of the liquid crystal composition.
A range of 9% by weight is suitable, but preferably 10-97% by weight, more preferably 40-95% by weight.

Among the third components, preferred examples of the compounds contained in the general formula (7) include the following formulas (7-1) to (7-1)
1) Formulas (8-1) to (8-18) as preferable examples of the compound included in the general formula (8), and Formulas (9-1) to (8) as a preferable example of the compound included in the general formula (9) Compounds represented by 9-6) can be exemplified.

[0062]

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[0063]

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[0064]

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[0065]

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(In each formula, R ₆ and R ₇ have the same meanings as described above. Further, each element constituting the compound of each formula may include those selected from their isotopes.) Are represented by the general formulas (7) to (9):
Compounds having a small absolute value of ε and close to zero, of which compounds of the general formula (7) are mainly used for adjusting the viscosity or Δn of the liquid crystal composition, and compounds of the general formulas (8) and (9) Is used for widening the nematic range of the liquid crystal composition such as increasing the clearing point and for adjusting Δn. This compound increases the threshold voltage of the liquid crystal composition as the amount used increases, but decreases the viscosity. Therefore, as long as the threshold voltage of the liquid crystal composition satisfies the required characteristics, the larger the amount used, the better. Under these circumstances, when preparing a liquid crystal composition for a TFT, the above-mentioned amount is suitably at most 40% by weight, preferably at most 35% by weight, based on the total weight of the liquid crystal composition. On the other hand, when preparing a liquid crystal composition for an STN display mode or a TN display mode, the above-mentioned amount is suitably at most 70% by weight, preferably at most 60% by weight, based on the total weight of the liquid crystal composition. .

Next, among the other components, the optically active compound is a special case, for example, OCB (optically).
Compensated Birefringenc
e) Except in the case of a liquid crystal composition for a mode, generally, a helical structure of the liquid crystal composition is induced to adjust a required twist angle,
Thus, it is added for the purpose of preventing reverse twist. This optically active compound is widely selected from known ones as long as the above-mentioned object is achieved, and preferably includes optically active compounds represented by the following formulas (Op-1) to (Op-8). it can.

[0068]

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By adding these optically active compounds, the pitch length of the twist of the liquid crystal composition is adjusted. The pitch length of this twist is such that the liquid crystal composition has a T
For FT and TN, the range is 40 to 200 μm, for STN, 6 to 20 μm, and for bistable TN (Bistable TN) mode, 1.5 to 200 μm. It is preferable to adjust each to the range of 4 μm. In this case, two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the pitch length.

The liquid crystal composition provided according to the present invention is generally prepared by a method known per se, for example, a method in which various components are mutually dissolved at a high temperature. If a dichroic dye such as a merocyanine-based, styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye is added during the preparation, a guest-host (GH) mode liquid crystal composition can be obtained. It can also be used as The liquid crystal composition according to the present invention includes NCAP prepared by microencapsulating a nematic liquid crystal,
Including polymer dispersed liquid crystal display (PDLCD) represented by polymer network liquid crystal display (PNLCD) made by forming three-dimensional network polymer in liquid crystal, birefringence control (ECB) mode and dynamic It can also be used as a liquid crystal composition for a scattering (DS) mode.

The nematic liquid crystal composition of the present invention is prepared as described above.
26 can be shown. In addition, in each composition example, according to the agreement shown in the following Table 1, the compound was shown in the column of the symbol of the left terminal group, the bonding group, the ring structure, and the group shown in each column of the right terminal group. The indication when trans-1,4-cyclohexylene and the hydrogen atom on the trans, trans-bicyclohexane-4,4′-diyl group are replaced by an isotope deuterium atom is shown below. When the above groups are represented by formulas (60) and (61), hydrogen atoms J1, J2, J
3, J4, J5, J6, J7 and J8 are each a corresponding deuterium atom 1D, 2D, 3D,
It is indicated by the symbol H [1D, ８8D] as being replaced by only one selected from 4D, 5D, 6D, 7D and 8D. Compound No. attached to the compound of the present invention Is the same as that shown in Examples described later, and the content of the compound means% by weight unless otherwise specified. The characteristic data of the composition examples are T _NI (nematic-isotropic liquid transition temperature or clearing point), η (viscosity: measurement temperature 20.0).
° C), Δn (refractive index anisotropy: measurement temperature 25.0 ° C), Δ
ε1 (dielectric anisotropy value: measurement temperature 25.0 ° C.), V
_th (threshold voltage: measured temperature 25.0 ° C.) and P (pitch: measured temperature 25 ° C.).

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[Table 1]

Composition Example 1 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 10.0% 1V2-BEB (F, F) -C 5.0% 3-HB-C 15.0% 1-BTB- 3 5.0% 2-BTB-1 10.0% 3-HH-4 11.0% 3-HHB-1 11.0% 3-HHB-3 9.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0% 3-HB (F) TB-2 6.0% 3-HB (F) TB-3 6.0% The results were as follows. T _NI = 88.1 ° C. η = 20.1 mPa · s Δn = 0.160 Δε1 = 7.6 V _th = 1.76 V In addition, 100 parts of the primary composition described above has the formula (Op−
0.8 parts of the optically active compound represented by 4) was added to obtain a secondary composition, and the characteristics of the secondary composition were obtained. The results were as follows. P = 10.5 μm

Composition Example 2 A liquid crystal composition having the following compound contents was prepared. F3-GB (F) -CF3 (No. 7) 5.0% F2-GHB (F) -OCF3 (No. 95) 5.0% V2-HB-C 12.0% 1V2-HB-C 12. 0% 3-HB-C 5.0% 3-H [1D, 2D, 3D] BC 9.0% 3-HB (F) -C 5.0% 2-BTB-1 2.0% 3 -HH-4 8.0% 3-HH-VFF 6.0% 2-H [1D, 2D, 3D] HB-C 3.0% 3-HHB-C 6.0% 3-HB (F) TB -2 8.0% 3-H2BTB-2 5.0% 3-H2BTB-3 5.0% 3-H2BTB-4 4.0% When the characteristics of this composition were determined, the results were as follows. T _NI = 81.5 ° C. η = 21.2 mPa · s Δn = 0.153 Δε1 = 7.8 V _th = 2.26 V

Composition Example 3 A liquid crystal composition having the following compound content was prepared. F5-GB-OCF3 (No. 13) 5.0% F3-HGB (F, F) -CF3 (No. 137) 2.0% 3O1-BEB (F) -C 13.0% 4O1-BEB (F ) -C 13.0% 5O1-BEB (F) -C 13.0% 2-HHB (F) -C 15.0% 3-HHB (F) -C 15.0% 3-HB (F) TB -2 4.0% 3-HB (F) TB-3 4.0% 3-HB (F) TB-4 4.0% 3-HHB-1 8.0% 3-HHB-O1 4.0% The properties of this composition were determined as follows. T _NI = 90.0 ° C. η = 76.4 mPa · s Δn = 0.146 Δε1 = 29.0 V _th = 1.04 V

Composition Example 4 A liquid crystal composition having the following compound contents was prepared. F2-G4B (F) -F (No. 22) 4.0% 5-PyB-F 4.0% 3-PyB (F) -F 4.0% 2-BB-C 5.0% 5-BB -C 5.0% 2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 6-PyB-O5 3.0% 6-PyB-O6 3.0 % 6-PyB-O7 3.0% 6-PyB-O8 3.0% 3-PyBB-F 6.0% 4-PyBB-F 6.0% 5-PyBB-F 6.0% 3-HHB- 1 6.0% 3-HHB-3 8.0% 2-H2BTB-2 4.0% 2-H2BTB-3 4.0% 2-H2BTB-4 5.0% 3-H2BTB-2 5.0% 3-H2BTB-3 5.0% 3-H2BTB-4 5.0% When the characteristics of this composition were determined, the results were as follows. T _NI = 90.6 ° C. η = 34.0 mPa · s Δn = 0.195 Δε1 = 5.9 V _th = 2.51 V

Composition Example 5 A liquid crystal composition having the following compound contents was prepared. F2-G2B (CL) -CL (No. 20) 4.0% 3-GB-C 10.0% 4-GB-C 10.0% 2-BEB-C 12.0% 3-PyB (F) -F 6.0% 3-HEB-O4 8.0% 4-HEB-O2 6.0% 5-HEB-O1 6.0% 3-HEB-O2 5.0% 5-HEB-O2 4.0 % 5-HEB-5 5.0% 4-HEB-5 5.0% 10-BEB-2 4.0% 3-HHB-1 6.0% 3-HHEBB-C 3.0% 3-HBEBB- C 3.0% 5-HBEBB-C 3.0% The properties of this composition were determined, and the results were as follows. T _NI = 63.0 ° C. η = 37.7 mPa · s Δn = 0.117 Δε1 = 10.7 V _th = 1.68 V

Composition Example 6 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 10.0% F2-GHB (F) -OCF3 (No. 95) 10.0% F2-G2B (F) B (F) -F (No. 124) 10.0% 3-HB-C 8.0% 7-HB-C 3.0% 1O1-HB-C 5.0% 3-HB (F) -C 5.0% 2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 1O1-HH-3 7.0% 2-BTB-O1 7.0% 3-HHB-1 2.0% 3-HHB-F 4.0% 3-HHB-O1 4.0% 3-HHB-3 3.0% 3-H2BTB-2 3.0% 3-H2BTB-3 3.0% 2 -PyBH-3 4.0% 3-PyBH-3 3.0% 3-PyBB-2 3.0%

Composition Example 7 A liquid crystal composition having the following compound contents was prepared. F5-GBEB (F) -CL (No. 63) 5.0% F2-G2HB (F) -OCF2CF2H (No. 119) 4.0% F3-HG4B (F, F) -F (No. 150) 4 3.0% 3O1-BEB (F) -C 4.0% 5O1-BEB (F) -C 4.0% 1V2-BEB (F, F) -C 10.0% 3-HH-EMe 10.0% 3-HB-O2 18.0% 7-HEB-F 2.0% 3-HHEB-F 2.0% 5-HHEB-F 2.0% 3-HBEB-F 4.0% 2O1-HBEB (F ) -C 2.0% 3-HB (F) EB (F) -C 2.0% 3-HBEB (F, F) -C 2.0% 3-HHB-F 4.0% 3-HHB- O1 4.0% 3-HHB-3 13.0% 3-HEBEB-F 2.0% 3-HEBEB-1 2.0% Was determined the characteristics of the formed product, it was as follows. T _NI = 87.4 ° C. η = 38.5 mPa · s Δn = 0.109 Δε1 = 19.6 V _th = 1.12 V

Composition Example 8 A liquid crystal composition having the following compound contents was prepared. F3-GHBB (F) -F (No. 152) 4.0% 5-BEB (F) -C 5.0% V-HB-C 11.0% 5-PyB-C 6.0% 4-BB -3 11.0% 3-HH-2V 10.0% 5-HH-V 11.0% V-HHB-1 7.0% V2-HHB-1 15.0% 3-HHB-1 5.0 % 1V2-HBB-2 10.0% 3-HHEBH-3 5.0% The characteristics of this composition were determined, and the results were as follows. T _NI = 89.6 ° C. η = 17.5 mPa · s Δn = 0.117 Δε1 = 5.0 V _th = 2.23 V

Composition Example 9 A liquid crystal composition having the following compound contents was prepared. F4-HHGB-CF3 (No. 191) 5.0% 3O1-BEB (F) -C 12.0% 5O1-BEB (F) -C 4.0% 1V2-BEB (F, F) -C 0% 3-HB-O2 10.0% 3-HH-4 3.0% 3-HHB-F 3.0% 3-HHB-1 8.0% 3-HHB-O1 4.0% 3-HBEB -F 4.0% 3-HHEB-F 7.0% 5-HHEB-F 7.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0 % 3-HB (F) TB-2 5.0% The characteristics of this composition were determined, and the results were as follows. T _NI = 100.1 ° C. η = 41.2 mPa · s Δn = 0.142 Δε1 = 26.7 V _th = 1.36 V

Composition Example 10 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 6.0% F2-GHB (F) -OCF3 (No. 95) 6.0% F3-HGB (F, F) -CF3 (No. 137) 6.0% 2-BEB-C 12.0% 3-BEB-C 4.0% 4-BEB-C 6.0% 3-HB-C 10.0% 3-HEB-O4 12.0% 4-HEB-O2 8.0% 5-HEB-O1 8.0% 3-HEB-O2 6.0% 5-HEB-O2 5.0% 3-HHB-1 7.0% 3 -HHB-O1 4.0% The characteristics of this composition were measured, and the results were as follows. T _NI = 60.0 ° C. η = 35.5 mPa · s Δn = 0.08 Δε1 = 9.5 V _th = 1.53 V

Composition Example 11 A liquid crystal composition having the following compound contents was prepared. F3-GB (F) -CF3 (No. 7) 4.0% F5-GB-OCF3 (No. 13) 3.0% 2-BEB-C 10.0% 5-BB-C 12.0% 1 -BTB-3 7.0% 2-BTB-1 10.0% 10-BEB-2 10.0% 10-BEB-5 12.0% 2-HHB-1 4.0% 3-HHB-F 4 0.0% 3-HHB-1 7.0% 3-HHB-O1 4.0% 3-HHB-3 13.0% The properties of this composition were determined, and the results were as follows. T _NI = 58.6 ° C. η = 19.8 mPa · s Δn = 0.146 Δε1 = 5.8 V _th = 2.01 V

Composition Example 12 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 2.0% F2-G2B (F) B (F) -F (No. 124) 2.0% F3-HGB (F, F) -CF3 (No. 137) 2.0% 1V2-BEB (F, F) -C 8.0% 3-HB-C 4.0% V2V-HB-C 14.0% V2V-HH-3 19.0% 3-HB-O2 4.0% 3-HHB-1 10.0% 3-HHB-3 15.0% 3-HB (F) TB-2 4.0% 3-HB (F) TB-3 4.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0% The properties of this composition were determined, and the results were as follows. . T _NI = 99.8 ° C. η = 20.9 mPa · s Δn = 0.129 Δε1 = 7.8 V _th = 2.25 V

Composition Example 13 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 5.0% F3-GB (F) -CF3 (No. 7) 5.0% 5-BTB (F) TB-3 10 0.0% V2-HB-TC 10.0% 3-HB-TC 10.0% 5-HB-C 7.0% 5-BB-C 3.0% 2-BTB-1 10.0% 2- 2. BTB-O1 5.0% 3-HH-4 5.0% 3-HHB-1 10.0% 3-HHB-3 11.0% 3-H2BTB-2 3.0% 3-H2BTB-3 0% 3-HB (F) TB-2 3.0% The characteristics of this composition were determined, and the results were as follows. T _NI = 92.0 ° C. η = 18.3 mPa · s Δn = 0.198 Δε1 = 6.6 V _th = 2.31 V

Composition Example 14 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 3.0% F3-GB (F) -CF3 (No. 7) 3.0% F5-GB-OCF3 (No. 13) 3.0% F2-GHB (F) -OCF3 (No. 95) 3.0% 1V2-BEB (F, F) -C 6.0% 3-HB-C 6.0% 2-BTB-1 10 0.0% 5-HH-VFF 30.0% 1-BHH-VFF 8.0% 1-BHH-2VFF 11.0% 3-H2BTB-2 5.0% 3-H2BTB-3 4.0% 3- H2BTB-4 4.0% 3-HHB-1 4.0% When the characteristics of this composition were determined, the results were as follows. T _NI = 72.4 ° C. η = 16.1 mPa · s Δn = 0.122 Δε1 = 5.8 V _th = 2.39 V

Composition Example 15 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 6.0% F5-GBEB (F) -CL (No. 63) 6.0% 2-HB-C 5.0% 3 -HB-O2 15.0% 2-BTB-1 3.0% 3-HHB-1 8.0% 3-HHB-F 4.0% 3-HHB-O1 5.0% 3-HHB-314 3.0% 3-HHEB-F 4.0% 5-HHEB-F 4.0% 2-HHB (F) -F 7.0% 3-HHB (F) -F 7.0% 5-HHB (F ) -F 7.0% 3-HHB (F, F) -F 5.0% The characteristics of this composition were determined, and the results were as follows. T _NI = 100.2 ° C. η = 25.7 mPa · s Δn = 0.097 Δε1 = 4.5 V _th = 2.64 V

Composition Example 16 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 5.0% F2-GHB (F) -OCF3 (No. 95) 4.0% F2-G2B (F) B (F) -F (No. 124) 4.0% 2-HHB (F) -F 17.0% 3-HHB (F) -F 17.0% 5-HHB (F) -F 16.0% 2-H2HB (F) -F 10.0% 3-H2HB (F) -F 5.0% 5-H2HB (F) -F 10.0% 2-HBB (F) -F 6.0% 3-HBB (F ) -F 6.0% The characteristics of this composition were measured, and the results were as follows. T _NI = 90.7 ° C. η = 28.8 mPa · s Δn = 0.086 Δε1 = 6.4 V _th = 1.60 V Further, the above-mentioned formula (Op−
0.3 part of the optically active compound represented by 8) was added to obtain a secondary composition, and the characteristics of the secondary composition were obtained. P = 78 μm

Composition Example 17 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 6.0% 7-HB (F) -F 5.0% 5-H2B (F) -F 5.0% 3-HB -O2 10.0% 3-HH-4 2.0% 3-HH [5D, 6D, 7D] -4 3.0% 2-HHB (F) -F 10.0% 3-HHB (F)- F 10.0% 5-HH [5D, 6D, 7D] B (F) -F 10.0% 3-H2HB (F) -F 5.0% 2-HBB (F) -F 3.0% 3 -HBB (F) -F 3.0% 2-H2BB (F) -F 5.0% 3-H2BB (F) -F 6.0% 3-HHB-1 8.0% 3-HHB-O15 3.0% 3-HHB-3 4.0% The properties of this composition were determined, and the results were as follows. T _NI = 84.5 ° C. η = 19.5 mPa · s Δn = 0.090 Δε1 = 4.4 V _th = 2.38 V

Composition Example 18 A liquid crystal composition having the following compound contents was prepared. F3-GB (F) -CF3 (No. 7) 4.0% F5-GB-OCF3 (No. 13) 4.0% F3-GHBB (F) -F (No. 152) 4.0% F4- HHGB-CF3 (No. 191) 4.0% 7-HB (F, F) -F 3.0% 3-HB-O2 7.0% 2-HHB (F) -F 10.0% 3-HHB (F) -F 10.0% 5-HHB (F) -F 10.0% 2-HBB (F) -F 9.0% 3-HBB (F) -F 9.0% 2-HBB-F 4.0% 3-HBB-F 4.0% 5-HBB-F 3.0% 3-HBB (F, F) -F 5.0% 5-HBB (F, F) -F 10.0% The properties of this composition were determined as follows. T _NI = 81.9 ° C. η = 25.1 mPa · s Δn = 0.104 Δε1 = 6.5 V _th = 1.64 V

Composition Example 19 A liquid crystal composition having the following compound contents was prepared. F2-G4B (F) -F (No. 22) 3.0% F2-GHB (F) -OCF3 (No. 95) 3.0% F3-HGB (F, F) -CF3 (No. 137) 3 3.0% F3-HG4B (F, F) -F (No. 150) 3.0% 7-HB (F, F) -F 3.0% 3-H2HB (F, F) -F 12.0% 4-H2HB (F, F) -F 10.0% 5-H2HB (F, F) -F 10.0% 3-HHB (F, F) -F 5.0% 4-HHB (F, F) -F 5.0% 3-HH2B (F, F) -F 15.0% 5-HH2B (F, F) -F 10.0% 3-HBB (F, F) -F 12.0% 3- HBCF2OB (F, F) -F 6.0% When the characteristics of this composition were determined, the results were as follows. T _NI = 68.5 ° C. η = 27.4 mPa · s Δn = 0.079 Δε1 = 8.8 V _th = 1.53 V

Composition Example 20 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 5.0% F2-G2HB (F) -OCF2CF2H (No. 119) 5.0% F5-GBEB (F) -Cl (No .63) 3.0% F3-GHBB (F) -F (No. 152) 3.0% 7-HB (F, F) -F 5.0% 3-H2HB (F, F) -F 0% 3-HHB (F, F) -F 10.0% 4-HHB (F, F) -F 5.0% 3-HBB (F, F) -F 10.0% 3-HHEB (F, F) -F 10.0% 4-HHEB (F, F) -F 3.0% 5-HHEB (F, F) -F 3.0% 2-HBEB (F, F) -F 3.0% 3-HBEB (F, F) -F 5.0% 3-HGB (F, F) -F 15.0% 3-HHBB (F, F) -F 3.0% The properties of this composition were determined. Time, was as follows. T _NI = 75.7 ° C. η = 40.3 mPa · s Δn = 0.081 Δε1 = 13.1 V _th = 1.39 V

Composition Example 21 A liquid crystal composition having the following compound contents was prepared. F2-G2B (CL) -CL (No. 20) 4.0% F2-GHB (F) -OCF3 (No. 95) 7.0% F3-HGB (F, F) -CF3 (No. 137) 7 0.0% 3-HB-CL 10.0% 5-HB-CL 4.0% 1O1-HH-5 5.0% 2-HBB (F) -F 8.0% 3-HBB (F) -F 8.0% 4-HHB-CL 8.0% 5-HHB-CL 8.0% 3-H2HB (F) -CL 4.0% 3-HBB (F, F) -F 10.0% 5- H2BB (F, F) -F 9.0% 3-HB (F) VB-2 4.0% 3-HB (F) VB-3 4.0% When the characteristics of this composition were determined, the following results were obtained. It was right. T _NI = 80.5 ° C. η = 23.8 mPa · s Δn = 0.122 Δε1 = 6.1 V _th = 1.76 V

Composition Example 22 A liquid crystal composition having the following compound contents was prepared. F3-GB (F, F) B (F) -F (No. 52) 4.0% F3-GB (F) -CF3 (No. 7) 4.0% F5-GB-OCF3 (No. 13) 4.0% F2-G2B (F) B (F) -F (No. 124) 4.0% F3-HGB (F, F) -CF3 (No. 137) 4.0% 3-HHB (F, F) -F 9.0% 3-H2HB (F, F) -F 8.0% 4-H2HB (F, F) -F 8.0% 5-H2HB (F, F) -F 8.0% 3-HBB (F, F) -F 21.0% 3-H2BB (F, F) -F 10.0% 5-HHBB (F, F) -F 3.0% 5-HHEBB-F 2.0 % 3-HH2BB (F, F) -F 3.0% 1O1-HBBH-4 4.0% 1O1-HBBH-5 4.0% The characteristics of this composition were determined as follows. It was right. T _NI = 82.5 ° C. η = 39.5 mPa · s Δn = 0.104 Δε1 = 9.4 V _th = 1.50 V

Composition Example 23 A liquid crystal composition having the following compound content was prepared. F2-GHB (F) -OCF3 (No. 95) 7.0% F5-GB-OCF3 (No. 13) 5.0% F2-G2B (F) B (F) -F (Product No. 124) 5 5.0% 5-HB-F 12.0% 6-HB-F 9.0% 7-HB-F 7.0% 3-HHB-OCF3 7.0% 4-HHB-OCF3 7.0% 5- HHB-OCF3 5.0% 3-HH2B-OCF3 4.0% 5-HH2B-OCF3 4.0% 3-HHB (F, F) -OCF3 5.0% 3-HBB (F) -F 10.0 3-HH2B (F) -F 3.0% 3-HB (F) BH-3 3.0% 5-HBBH-3 3.0% 3-HHB (F, F) -OCF2H 4.0% The properties of the composition were determined as follows. T _NI = 68.1 ° C. η = 19.0 mPa · s Δn = 0.082 Δε1 = 4.7 V _th = 2.21 V

Composition Example 24 A liquid crystal composition having the following compound contents was prepared. F2-G2B (F) B (F) -F (No. 124) 5.0% 5-H4HB (F, F) -F 7.0% 5-H4HB-OCF3 15.0% 3-H4HB (F, 10. F) -CF3 8.0% 5-H4HB (F, F) -CF3 10.0% 3-HB-CL 6.0% 5-HB-CL 4.0% 3-H2BB (F) -F 0% 5-HVHB (F, F) -F 5.0% 3-HHB-OCF3 5.0% 3-H2HB-OCF3 5.0% V-HHB (F) -F 5.0% 3-HHB ( F) -F 5.0% 5-HHEB-OCF3 2.0% 3-HBEB (F, F) -F 5.0% 5-HH-V2F 3.0% When the characteristics of this composition were determined, It was as follows. T _NI = 65.9 ° C. η = 28.4 mPa · s Δn = 0.092 Δε1 = 8.4 V _th = 1.62 V

Composition Example 25 A liquid crystal composition having the following compound contents was prepared. F3-GB (F) -CF3 (No. 7) 5.0% F2-G2HB (F) -OCF2CF2H (No. 119) 5.0% F3-HGB (F, F) -CF3 (No. 137) 5 0.0% F3-GHBB (F) -F (No. 152) 4.0% 2-HHB (F) -F 2.0% 3-HHB (F) -F 2.0% 5-HHB (F) -F 2.0% 2-HBB (F) -F 6.0% 3-HBB (F) -F 6.0% 3-H2BB (F) -F 9.0% 3-HBB (F, F) -F 25.0% 5-HBB (F, F) -F 19.0% 1O1-HBBH-4 5.0% 1O1-HBBH-5 5.0% The characteristics of this composition were determined as follows. It was right. T _NI = 93.6 ° C. η = 40.8 mPa · s Δn = 0.125 Δε1 = 8.1 V _th = 1.58 V Also, 100 parts of the primary composition described above has the formula (Op−
0.25 parts of the optically active compound represented by 5) was added to obtain a secondary composition, and the characteristics of the secondary composition were obtained. The results were as follows. P = 62 μm

Composition Example 26 A liquid crystal composition having the following compound contents was prepared. F5-GB-OCF3 (No. 13) 2.0% 5-HB-CL 10.0% 3-HH-4 7.0% 3-HB-O2 20.0% 3-H2HB (F, F)- F 8.0% 3-HHB (F, F) -F 8.0% 3-HBB (F, F) -F 6.0% 2-HHB (F) -F 5.0% 3-HHB (F ) -F 5.0% 5-HHB (F) -F 5.0% 2-H2HB (F) -F 2.0% 3-H2HB (F) -F 1.0% 5-H2HB (F)- F 2.0% 3-HHBB (F, F) -F 4.0% 3-HBCF2OB-OCF3 4.0% 5-HBCF2OB (F, F) -CF3 4.0% 3-HHB-1 3.0 % 3-HHB-O1 4.0%

The compounds represented by the general formula (1) according to the present invention have the formulas (1-a), (1-b) to (1-b) as described above.
d), (1-e) and (1-f) to (1-h), which are publicly known documents, for example, the 4th edition of Experimental Chemistry Course (Maruzen), J. Am. Org. Che
m. , 42 , 1821 (1977) and J. Amer. Che
m. Soc. Perkin Trans. 2,2041
(1989) can be easily produced.

In the above production, a 1,3-propanediol derivative corresponding to the compound group is required as one of the raw materials. First, an example of the synthesis of the derivative is shown below. 1,3-for compounds represented by formulas (1-a) to (1-d)
Synthesis of propanediol derivative: Fluoroalkyl bromide (17) and diethyl malonate (18) are allowed to act in the presence of potassium carbonate in an alcohol solvent to give compound (1).
9), and lithium aluminum hydride (hereinafter referred to as L)
Abbreviated as AH. ) In an aprotic solvent such as tetrahydrofuran (hereinafter abbreviated as THF) to obtain the 1,3-propanediol derivative (20) for the title use.

For the compound represented by the formula (1-e),
Synthesis of propanediol derivative: Compound (22) synthesized from fluoroalkyl bromide (17) and triphenylphosphine is mixed with THF together with a base such as potassium t-butoxide in THF to produce ylide, and cyclohexanedione monoethylene The compound (23) is obtained by reacting the ketal (21) with Pd (0) or Nd.
Hydrogenation is performed in the presence of the i (0) catalyst, followed by addition of an acid for deprotection to obtain the cyclohexanone derivative (24). Ethyl diethylphosphonoacetate and sodium hydride were added to this product, and the mixture was subjected to Wittig-Horner reaction (see the 4th edition, Experimental Chemistry Lecture (Maruzen), Vol. 19, pp. 74-77) to obtain compound (25). After hydrogenation to give an ethyl ester derivative (26), compound (27) is obtained by reacting lithium diisopropylamide (hereinafter abbreviated as LDA) and methyl chlorocarbonate in this order in an aprotic solvent such as THF. The 1,3-propanediol derivative (28) for the title use can be obtained by allowing LAH to act on this. Synthesis of 1,3-propanediol derivative for compound represented by formula (1-h): 1,3-propanediol derivative (28) except that cyclohexanedione monoethylene ketal (21) is replaced with compound (29) The title 1,3-propanediol derivative (30) can be obtained in the same manner as in the method for obtaining (1).

[0103]

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The compound of the present invention can be suitably obtained by using the thus obtained 1,3-propanediol derivative as one of the raw materials. Production of Compound Represented by Formula (1-a): (Compound of n2 = 0) A benzaldehyde derivative (31) is added to a 1,3-propanediol derivative (20) in the presence of an acid catalyst such as paratoluenesulfonic acid. It can be obtained by acting. (Compound with n2 = 1) benzaldehyde derivative (3
1), using ethyl diethylphosphonoacetate and sodium hydride,
The compound (32) is subjected to a reaction, and hydrogenated to form an ethyl ester derivative (33), and then treated with a reducing agent such as diisobutylaluminum hydride (hereinafter abbreviated as DIBAL) to react with the aldehyde derivative (34). Get) Except that this compound is used in place of the benzaldehyde derivative (31), the same as in the case of obtaining the compound of n2 = 0,
Reacting with a 3-propanediol derivative (20),
The title compound can be obtained. (Compound of n2 = 2) n2 except that the aldehyde derivative (34) is used in place of the benzaldehyde derivative (31).
Aldehyde derivative (35) was obtained in the same manner as in the case of obtaining the compound of formula (1) = 1, and then used in place of the benzaldehyde derivative (31) in the same manner as in the case of obtaining the compound of n2 = 0, except that this was used. The title compound can be obtained by reaction with the propanediol derivative (20).

[0105]

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(Wherein Q ₁ , Q ₂ and Y have the same meanings as described above.) Production of the compound represented by the formula (1-b): (Compound wherein Zb is a single bond) 1,3 A benzaldehyde derivative (36) is allowed to act on a propanediol derivative (20) in the presence of an acid catalyst such as paratoluenesulfonic acid to obtain a phenyldioxane derivative (37), to which butyllithium (BuLi) is added at approximately -50 ° C; Acting below gives the lithiated product (38). The title compound can be obtained by subjecting this to a known method for synthesizing a homobiaryl compound, and there are usually two methods. One of them is J.S. Org. Chem. , 42 , 18
21 (1977), the lithiated product (3
8) A method in which zinc chloride, Pd (0) and a bromobenzene derivative (39) are successively acted on in this order. Another one is described in J.I. Chem. Soc. Perkin Tra
ns. 2,2041 (1989),
(A) a product obtained by iodination of a lithiated product (38) and (b) a boronic acid derivative (40) obtained from a Grignard reagent prepared from the bromobenzene derivative (39) and a trialkyl borate, In this method, a coupling reaction is performed in the presence of a catalyst such as (0).

(Compound in which Zb is -COO-) The lithiated product (38 is reacted with carbon dioxide to form a carboxylic acid Derivative (41) was obtained.
According to a method described on page 6, a phenol derivative (4
2) is allowed to act in the coexistence of 4-dimethylaminopyridine and 1,3-dicyclohexylcarbodiimide (hereinafter abbreviated as DCC) to give an ester (4) of the title compound.
3) can be obtained.

(Compound wherein Zb is —CF ₂ O—) Bu
ll. Soc. Chim. Belg. , 87 , 293
Based on the method described in (1978), a thione ester (44) was obtained by reacting the above-mentioned ester (43) with a Lawesson's reagent, and this was treated with diethylaminosulfur trifluoride (hereinafter referred to as D) in methylene chloride or glyme solvent.
Abbreviated as AST. ) Or JP-A-6-2
No. 63679, tetrabutylammonium dihydrogen trifluoride (hereinafter abbreviated as TBAH2F3) in methylene chloride or 1,2-dichloroethane.
And N-iodinated succinimide (hereinafter abbreviated as NIS) to give the title compound.

[0109]

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(In the formula, Q ₁ , Q ₂ and Y have the same meanings as described above.) Production of the compound represented by the formula (1-c): (Compound wherein Zb is a single bond) The cyclohexanedione A monoethylene ketal (21) is reacted with a Grignard reagent (45) prepared from a bromobenzene derivative (39) and magnesium to give a compound (46), which is dehydrated with an acid and then hydrogenated to give a compound (47). ), And then deprotected using an acid to obtain a cyclohexanone derivative (48). This is reacted with methoxymethyltriphenylphosphonium chloride and an ylide obtained from a base, and then deprotected with an acid to give an aldehyde derivative (4
9) is obtained. This product was converted to a benzaldehyde derivative (3
A reaction with a 1,3-propanediol derivative (20) was carried out in the same manner as in the production of the compound (n2 = 0) represented by the formula (1-a) except that the title compound was used in place of 1). Can be obtained. (Compound wherein Zb is —CH ₂ CH ₂ —) Compound (50)
Is used in place of the Grignard reagent compound (45), and the title compound can be obtained in the same manner as in the method for obtaining a compound in which Zb is a single bond.

[0111]

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(Wherein Q ₁ , Q ₂ and Y have the same meanings as described above). Preparation of the compound represented by the formula (1-d): (n3 = 1, ring A1 is represented by the formula (a) Compound represented by the formula) Except that the aldehyde derivative (49) is used in place of the benzaldehyde derivative (31), the aldehyde derivative is produced in the same manner as in the production of the compound (n2 = 1) represented by the formula (1-a) Formula (1-a) except that (51) is obtained and then this is used in place of the benzaldehyde derivative (31).
The reaction with the 1,3-propanediol derivative (20) is carried out in the same manner as in the production of the compound represented by the formula (n2 = 0) to obtain the title compound. (Compound in which n3 = 2 and ring A1 is (a)) Compound in which n3 = 1 and ring A1 is represented by formula (a) except that aldehyde derivative (51) is used in place of aldehyde derivative (49) The title compound can be obtained in the same manner as in the method for obtaining the title compound. (Compound wherein n3 is 1 or 2, and ring A1 is (b), (c) or (e)) In the production of the compound represented by the formula (1-a), Y is a hydrogen atom, Q ₁ and Q ₂ Wherein each is independently a hydrogen atom or a fluorine atom (52)
And then using this compound instead of the phenyldioxane derivative (37) in the same manner as in the production of the compound represented by the formula (1-b) (compound in which Zb is a single bond). Can be obtained.

[0113]

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(In the formula, Q ₁ , Q ₂ and Y have the same meanings as described above.) Production of the compound represented by the formula (1-e): 1,3-propanediol derivative (28) The title compound can be obtained in the same manner as in the case of producing the compound represented by the formula (1-a) except that the compound is used instead of the 2,3-propanediol derivative (20). Production of the compound represented by the formula (1-h): represented by the formula (1-a) except that the 1,3-propanediol derivative (30) is used in place of the 1,3-propanediol derivative (20). The title compound can be obtained in the same manner as in the production of the compound. Production of the compound represented by the formula (1-f) or (1-g): The compound represented by the formula (1-a) to (1-e) can be obtained by appropriately using the production method described above. . Preparation of compound having a silinane ring: 1-sila- or 4
A compound having a silinane ring typified by -sila-1,4-cyclohexylene can be produced by applying the method described in JP-A-7-70148.

[0115]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. In each example, C indicates a crystal, S indicates a smectic phase, N indicates a nematic phase, and I indicates an isotropic liquid phase.

Example 1 5- (3-fluoropropyl) -2- (4- (3,4-
Difluorophenyl) -3,5-difluorophenyl)
-1,3-dioxane (in the general formula (1), n0 =
3, n1 = n2 = n4 = 0, n3 = 1, ring A1 = group represented by formula (e), Zb = single bond, Q1 = fluorine atom, Q2 = hydrogen atom, Y = fluorine atom ( N
o. 52)) Manufacturing

First stage 3-fluorobromopropane 2 in 1.3 l of ethanol
31 g (1.64 mol), diethyl malonate 263 g
(1.64 mol) and 226 g of potassium carbonate (1.
64 mol) and refluxed for 10 hours. The reaction solution was filtered using celite, the solvent in the filtrate was distilled off, and the residue was extracted with hexane. The extract was washed with water and dried over magnesium sulfate, and then the solvent was distilled off to obtain 223 g (1.01 mol) of diethyl 3-fluoropropylmalonate. Its yield from 3-fluorobromopropane was 61.
6%. 2nd stage 11 l of THF was added to 57.6 g (1.52 mol) of LAH, and the mixture was cooled to 5 ° C. To this was added dropwise a solution of 223 g (1.01 mol) of diethyl 3-fluoropropylmalonate in 100 ml of THF so as not to exceed 20 ° C. After stirring at 10 ° C for 20 minutes, 50 ml of water was added dropwise so that the temperature did not exceed 20 ° C, and the mixture was stirred for 10 minutes.
80 ml of OH was added dropwise. The reaction solution was further stirred at room temperature for 30 minutes, 5 g of magnesium sulfate was added, and the mixture was filtered using celite, and the solvent was distilled off. 137 g of 2- (3-fluoropropyl) -1,3-propanediol (1.
01 mol). This reaction proceeded almost quantitatively. Third stage 71 g (0.52 mol) of this product and 96 g (0.68 mol) of 3,5-difluorobenzaldehyde were dissolved in 500 ml of toluene, and 17 g of paratoluenesulfonic acid (hereinafter abbreviated as PTS) was added. The mixture was refluxed for 3 hours while being dehydrated. The reaction solution thus obtained was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and then the solvent was distilled off. The residue was recrystallized twice using heptane to give 5- (3-fluoropropyl) -2- (3,5-difluorophenyl) -1,
29 g (0.11 mol) of 3-dioxane were obtained. Its yield from 3,5-difluorobenzaldehyde was 21.2%.

Fourth stage 5.0 g (19.2 mmol) of the above product was added to THF 50
The mixture was dissolved in ml and cooled to −60 ° C. under a nitrogen atmosphere. A 1.60 M hexane solution of n-butyllithium 1 was added to this solution.
5.0 ml (24.0 mmol) was added dropwise while keeping the liquid temperature not exceeding -55 ° C, and the mixture was stirred at that temperature for 1 hour. Then, 0.5M of zinc chloride was added to the reaction solution.
After 48.0 ml (24.0 mmol) of a THF solution was added dropwise while keeping the liquid temperature not exceeding -55 ° C, the mixture was heated to room temperature and stirred for 30 minutes. 0.5 g of tetrakistriphenylphosphine palladium and 1-bromo-3,
4.63 g (24.0 mmol) of 4-difluorobenzene
l) was added and the mixture was refluxed for 3 hours and 30 minutes. 100 ml of water was added to the obtained reaction solution, the product was extracted with toluene, and the extract was washed with 3N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine in that order, dried over magnesium sulfate, and then the solvent was distilled off.
The residue was purified by column chromatography using heptane / ethyl acetate = 5/1 as a developing solvent, the solvent was distilled off, and the residue was recrystallized twice with heptane to give 5- (3-fluoro Propyl) -2- (4- (3,4-
Difluorophenyl) -3,5-difluorophenyl)
3.87 g (10.4 mmol) of -1,3-dioxane
I got 5- (3-fluoropropyl) -2 of this product
The yield from-(3,5-difluorophenyl) -1,3-dioxane was 54.2%. 1H-NMR (CDCl3) [delta] (ppm): 7.39-
7.02 (m, 5H), 5.40 (s, 1H), 4.7
2 (t, 1H), 4.37 to 4.13 (m, 3H),
3.69 to 3.44 (m, 2H), 2.28 to 1.12
(M, 4H). CI 54.1 ° C

Based on the description in Example 1 and the column of the detailed description of the invention, the following compound No. 1 to No. 217
Can be manufactured. In addition, the compound obtained in Example 1 is shown again below.

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[0121]

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[0125]

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[0132]

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[0133]

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[0136]

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[0139]

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[0140]

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[0141]

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Example 2 (Use Example 1) Nematic liquid crystal composition containing a cyanophenylcyclohexane-based liquid crystal compound (hereinafter sometimes referred to as liquid crystal composition A1): 4- (4-propylcyclohexyl) benzonitrile 24% 4- (4-pentylcyclohexyl) benzonitrile 36% 4- (4-heptylcyclohexyl) benzonitrile 25% 4- (4- (4-pentylcyclohexyl) phenylbenzonitrile 15% has the following properties: Clearing point ( T _NI ): threshold voltage (V _th ) at 71.7 ° C., cell thickness 8.8 μm: 1.78 V, Δε: 11.0, Δ
n: 0.137, viscosity (η) at 20 ° C .: 26.3
mPa · s. In 85% by weight of the liquid crystal composition A1, the 5- (3-fluoropropyl) -2- (4- (3,4-
Difluorophenyl) -3,5-difluorophenyl)
A liquid crystal composition B1 was prepared by mixing 15% by weight of -1,3-dioxane (Compound No. 52). This one is -2
Even when left at 0 ° C. for 30 days, it shows a nematic phase,
Its properties were as follows: Transparent point (T _NI ): threshold voltage (V _th ) at 63.5 ° C., cell thickness 9.0 μm: 1.40 V, Δε: 12.2, Δ
n: 0.132, viscosity at 20 ° C. (η): 36.8
mPa · s. The compound No. was determined from the physical properties of each of the liquid crystal compositions and the mixing ratio of the contained compounds. The values of the physical properties of No. 52 calculated by the extrapolation method were as follows. Clearing point (T _NI ): 17.0 ° C., Δε: 19.0, Δn:
0.104, viscosity at 20 ° C. (η): 95.7 mP
a · s.

[0143]

As described above, the liquid crystal compound of the present invention has an extremely large Δε, a high specific resistance, is electrically and chemically stable, and has a compatibility with the existing liquid crystal compound. Is also good. Therefore, when the liquid crystal compound of the present invention is used as a component of a liquid crystal composition, low voltage driving of a liquid crystal display element, particularly, a TFT type liquid crystal display element can be achieved.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yasuhiro Kubo 2-17-17 Tatsumidaihigashi, Ichihara-shi, Chiba (72) Inventor Fusayuki Takeshita 939-5 Nakatomi, Kimitsu-shi, Chiba 5 (72) Inventor Etsuo Nakagawa Chiba-shi 8890 Goi, Hara-shi

Claims (31)

[Claims] 1. A compound of the general formula (1) (Where n0 is an integer of 2 to 10, n1 and n2
Are each independently an integer of 0 to 2, n3 and n
4 is each independently 0 or 1, but n3 ≧ n4
And n1 + n3 + n4 ≦ 2, Q ₁ and Q ₂ each independently represent a hydrogen atom, a fluorine atom or a chlorine atom, Za, Zb and Zc each independently represent a single bond,
_{-CH 2 CH 2 -, - CH} 2 CH 2 CH 2 CH 2 -, - COO
— Or —CF ₂ O—, wherein ring A1 and ring A2 are each independently of the formulas (a) to (i) And Y represents a hydrogen atom, a halogen atom or a halogenated alkyl group having 1 to 5 carbon atoms. When the halogen atom is a fluorine atom, n1
= N2 = n4 = 0, n3 = 1, Zb = single bond and ring A
1 is not a group represented by the formula (b), and the halogenated alkyl group may be one in which one or more non-adjacent methylene groups in the group are replaced by an oxygen atom or a sulfur atom. Each element constituting the compound may include those selected from isotopes thereof. ). 2. The dioxane derivative according to claim 1, wherein n1 = n3 = n4 = 0. 3. The dioxane derivative according to claim 1, wherein n1 + n3 + n4 = 1. 4. The dioxane derivative according to claim 1, wherein n1 + n3 + n4 = 2. 5. The dioxane derivative according to claim 1, wherein n2 ≠ 0 and n3 = 1. 6. A compound of the formula (a) wherein n2 = 0 and n3 = 1 and the ring A1 has the formula (a)
The dioxane derivative according to claim 1, which is a group represented by the formula: 7. A compound of the formula (c) wherein n2 = 0, n3 = 1 and ring A1 is
The dioxane derivative according to claim 1, which is a group selected from the group consisting of (g). 8. A liquid crystal composition comprising at least one dioxane derivative according to claim 1. 9. A composition comprising, as a first component, at least one dioxane derivative according to any one of claims 1 to 7,
As the second component, general formulas (2), (3) and (4) (In each formula, R ₃ , Y ₁ , L ₁ , L ₂ , Z ₁ and Z ₂ may be the same or different between each formula, and R ₃ is an alkyl group having 1 to 10 carbon atoms. Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH
ＣＨCH— may be substituted, and any hydrogen atom may be substituted by a fluorine atom. Y ₁ is a fluorine atom,
Chlorine atom, OCF ₃ , OCF ₂ H, CF ₃ , CF ₂ H, CF
H ₂ , OCF ₂ CF ₂ H or OCF ₂ CFHCF ₃ , L ₁ and L ₂ each independently represent a hydrogen atom or a fluorine atom, Z ₁
And Z ₂ are each independently -CH ₂ CH _2- , -CH ₂ CH
_{2 CH 2 CH 2 -, -} COO -, - CF 2 O -, - OCF 2
-, -CH = CH- or a single bond is shown. Ring B is trans-1,4-cyclohexylene, 1,3-dioxane-
2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, ring C is trans-1,4
-Cyclohexylene or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A liquid crystal composition comprising at least one compound selected from the group consisting of: 10. The first component contains at least one dioxane derivative according to any one of claims 1 to 7, and the second component has the general formula (5) and / or (6). (In each formula, R ₄ and R ₅ are each independently a C 1-10
Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH = CH-
And any hydrogen atom may be substituted with a fluorine atom. Y ₂ represents a —CN group or —C≡
C-CN, ring E is trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5
-Diyl or pyrimidine-2,5-diyl, ring G is trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl in which a hydrogen atom may be substituted by a fluorine atom, ring H is Trans-1,4-cyclohexylene or 1,4-phenylene, Z ₃ is --C
H ₂ CH ₂ —, —COO— or a single bond, L ₃ , L ₄ and L ₅ each independently represent a hydrogen atom or a fluorine atom;
b, c and d are each independently 0 or 1. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A) a liquid crystal composition comprising at least one compound selected from the group consisting of: 11. A first component containing at least one dioxane derivative according to any one of claims 1 to 7, and a second component represented by general formulas (2), (3) and (4). 5] (In each formula, R ₃ , Y ₁ , L ₁ , L ₂ , Z ₁ and Z ₂ may be the same or different between each formula, and R ₃ is an alkyl group having 1 to 10 carbon atoms. Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH
ＣＨCH— may be substituted, and any hydrogen atom may be substituted by a fluorine atom. Y ₁ is a fluorine atom,
Chlorine atom, OCF ₃ , OCF ₂ H, CF ₃ , CF ₂ H, CF
H ₂ , OCF ₂ CF ₂ H or OCF ₂ CFHCF ₃ , L ₁ and L ₂ each independently represent a hydrogen atom or a fluorine atom, Z ₁
And Z ₂ are each independently -CH ₂ CH _2- , -CH ₂ CH
_{2 CH 2 CH 2 -, -} COO -, - CF 2 O -, - OCF 2
-, -CH = CH- or a single bond is shown. Ring B is trans-1,4-cyclohexylene, 1,3-dioxane-
2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, ring C is trans-1,4
-Cyclohexylene or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom. In the compounds of each formula, each element constituting them may include those selected from their isotopes. ), And at least one compound selected from the group consisting of the following general formulas (7), (8) and (9): (In each formula, R ₆ , R ₇ , I, J and K may be the same or different between the formulas, and R ₆ and R ₇ are each independently an alkyl group having 1 to 10 carbon atoms. In the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or —CH ＝ CH—, and any hydrogen atom may be substituted with a fluorine atom. , J
And K are each independently trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom;
Z ₄ and Z ₅ are each independently —C≡C—, —COO
—, —CH ₂ CH ₂ —, —CH ＝ CH— or a single bond. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A liquid crystal composition comprising at least one compound selected from the group consisting of: 12. The first component contains at least one dioxane derivative according to any one of claims 1 to 7, and the second component has the general formula (5) and / or (6). (In each formula, R ₄ and R ₅ are each independently a C 1-10
Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH = CH-
And any hydrogen atom may be substituted with a fluorine atom. Y ₂ represents a —CN group or —C≡
C-CN, ring E is trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5
-Diyl or pyrimidine-2,5-diyl, ring G is trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl in which a hydrogen atom may be substituted by a fluorine atom, ring H is Trans-1,4-cyclohexylene or 1,4-phenylene, Z ₃ is --C
H ₂ CH ₂ —, —COO— or a single bond, L ₃ , L ₄ and L ₅ each independently represent a hydrogen atom or a fluorine atom;
b, c and d are each independently 0 or 1. In the compounds of each formula, each element constituting them may include those selected from their isotopes. And at least one compound selected from the group consisting of compounds represented by the following general formulas (7), (8) and (9): (In each formula, R ₆ , R ₇ , I, J and K may be the same or different between the formulas, and R ₆ and R ₇ are each independently an alkyl group having 1 to 10 carbon atoms. In the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or —CH ＝ CH—, and any hydrogen atom may be substituted with a fluorine atom. , J
And K are each independently trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom;
Z ₄ and Z ₅ are each independently —C≡C—, —COO
—, —CH ₂ CH ₂ —, —CH ＝ CH— or a single bond. In the compounds of each formula, each element constituting them may include one selected from their isotopes. A liquid crystal composition comprising at least one compound selected from the group consisting of: 13. The first component contains at least one dioxane derivative according to any one of claims 1 to 7, and as a part of the second component, the general formulas (2), (3) and (4) Embedded image (In each formula, R ₃ , Y ₁ , L ₁ , L ₂ , Z ₁ and Z ₂ may be the same or different between each formula, and R ₃ is an alkyl group having 1 to 10 carbon atoms. Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH
ＣＨCH— may be substituted, and any hydrogen atom may be substituted by a fluorine atom. Y ₁ is a fluorine atom,
Chlorine atom, OCF ₃ , OCF ₂ H, CF ₃ , CF ₂ H, CF
H ₂ , OCF ₂ CF ₂ H or OCF ₂ CFHCF ₃ , L ₁ and L ₂ each independently represent a hydrogen atom or a fluorine atom, Z ₁
And Z ₂ are each independently -CH ₂ CH _2- , -CH ₂ CH
_{2 CH 2 CH 2 -, -} COO -, - CF 2 O -, - OCF 2
-, -CH = CH- or a single bond is shown. Ring B is trans-1,4-cyclohexylene, 1,3-dioxane-
2,5-diyl or 1,4-phenylene in which a hydrogen atom may be substituted by a fluorine atom, ring C is trans-1,4
-Cyclohexylene or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom. In the compounds of each formula, each element constituting them may include those selected from their isotopes. ) And at least one compound selected from the group consisting of compounds represented by general formulas (5) and / or (6): (In each formula, R ₄ and R ₅ are each independently a C 1-10
Wherein, in the alkyl group, one or more non-adjacent methylene groups are an oxygen atom or -CH = CH-
And any hydrogen atom may be substituted with a fluorine atom. Y ₂ represents a —CN group or —C≡
C-CN, ring E is trans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5
-Diyl or pyrimidine-2,5-diyl, ring G is trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl in which a hydrogen atom may be substituted by a fluorine atom, ring H is Trans-1,4-cyclohexylene or 1,4-phenylene, Z ₃ is --C
H ₂ CH ₂ —, —COO— or a covalent bond, L ₃ , L ₄ and L ₅ each independently represent a hydrogen atom or a fluorine atom, and b, c and d each independently represent 0 or 1.
In the compounds of each formula, each element constituting them may include those selected from their isotopes. And at least one compound selected from the group consisting of compounds represented by the following general formulas (7), (8) and (9): (In each formula, R ₆ , R ₇ , I, J and K may be the same or different between the formulas, and R ₆ and R ₇ are each independently an alkyl group having 1 to 10 carbon atoms. In the alkyl group, one or more non-adjacent methylene groups may be substituted with an oxygen atom or —CH ＝ CH—, and any hydrogen atom may be substituted with a fluorine atom. , J
And K are each independently trans-1,4-cyclohexylene, pyrimidine-2,5-diyl or 1,4-phenylene in which a hydrogen atom may be replaced by a fluorine atom;
Z ₄ and Z ₅ are each independently —C≡C—, —COO
—, —CH ₂ CH ₂ —, —CH ＝ CH— or a single bond. In the compounds of each formula, each element constituting them may include those selected from their isotopes. A liquid crystal composition comprising at least one compound selected from the group consisting of: 14. The liquid crystal composition according to claim 8, further comprising an optically active compound. 15. The liquid crystal composition according to claim 9, further comprising an optically active compound. 16. The liquid crystal composition according to claim 10, further comprising an optically active compound. 17. The liquid crystal composition according to claim 11, further comprising an optically active compound. 18. The liquid crystal composition according to claim 12, further comprising an optically active compound. 19. The liquid crystal composition according to claim 13, further comprising an optically active compound. 20. A liquid crystal display device comprising the liquid crystal composition according to claim 8. 21. A liquid crystal display device comprising the liquid crystal composition according to claim 9. 22. A liquid crystal display device comprising the liquid crystal composition according to claim 10. 23. A liquid crystal display device comprising the liquid crystal composition according to claim 11. 24. A liquid crystal display device comprising the liquid crystal composition according to claim 12. 25. A liquid crystal display device comprising the liquid crystal composition according to claim 13. 26. A liquid crystal display device comprising the liquid crystal composition according to claim 14. 27. A liquid crystal display device comprising the liquid crystal composition according to claim 15. 28. A liquid crystal display device comprising the liquid crystal composition according to claim 16. 29. A liquid crystal display device comprising the liquid crystal composition according to claim 17. 30. A liquid crystal display device comprising the liquid crystal composition according to claim 18. 31. A liquid crystal display device comprising the liquid crystal composition according to claim 19.