JPH11131065A - Liquid crystal composition and liquid crystal element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal composition useful for a ferroelectric liquid crystal element, capable of providing an excellent quick responsiveness, memory stability, orientation, high contrast ratio, etc., by including a specific optically active naphthalene compound and non-optically active ester compound. SOLUTION: This composition comprises (A) a compound of formula I [R1 is a 3-24C (branched) alkyl; R* is a (halogen or alkoxy-substituted) 3-24C alkyl having an optically active asymmetric carbon; Y1 is a single bond or -O-; Y2 is -COO- or -CH2 O-; X1 and X2 are each H or a halogen; and (n1 ) is 0 or 1] and (B) a compound of formula II [R2 and R3 are each a (halogen-substituted) 3-24C (branched) (un)saturated (alkoxy) alkyl, etc.; Y3 is a single bond, -O-, -COO-, etc.; and X3 is H or a halogen]. The composition comprises e.g. 50 to 97 wt.% of component A and 3 to 50 wt.% of component B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel liquid crystal composition. More specifically, the present invention relates to a liquid crystal composition useful as a component of a liquid crystal element such as a display element, and a liquid crystal element using the liquid crystal composition.

[0002]

2. Description of the Related Art At present, a TN (twisted nematic) type display system is most widely used as a liquid crystal display device. This TN type display system is inferior to a light emitting type device (cathode tube, electroluminescence, plasma display, etc.) in response time.
STN with a twist angle of 180-270 ° (Super
Twisted nematic display devices have also been developed, but their response times are still poor. Although various efforts have been made in this way, a TN type display element having a short response time has not been realized. However, in a new display system using a ferroelectric liquid crystal, which has been actively studied in recent years, there is a possibility that the response time can be significantly improved [NA Clark et al .; Applied Phys.lett., 36 , 899].
(1980)].

This method utilizes a chiral smectic phase such as a chiral smectic C phase exhibiting ferroelectricity. The ferroelectric phase is chiral smectic C
Not only phase but also chiral smectic F, G, H, I
It is known that such a phase is a ferroelectric liquid crystal phase exhibiting ferroelectricity. These smectic liquid crystal phases belong to a tilt type chiral smectic phase, but practically, chiral smectic C, which has a low viscosity among them, is used.
Phases are preferred. Various liquid crystal compounds exhibiting a chiral smectic C phase have been studied so far, and many compounds have already been searched for and manufactured. However, there are many characteristics (high-speed response, alignment, high contrast ratio, memory stability, and temperature dependence of these characteristics, etc.) required for application to the ferroelectric liquid crystal display device actually used. At present, a single compound cannot be used for optimization, and a ferroelectric liquid crystal composition obtained by mixing several liquid crystal compounds is used.

The ferroelectric liquid crystal composition includes not only a ferroelectric liquid crystal composition comprising only a compound exhibiting a ferroelectric liquid crystal phase, but also a non-chiral smectic C in JP-A-61-195187. It has been reported that a compound or composition exhibiting a phase is used as a basic substance, and one or more compounds exhibiting a ferroelectric liquid crystal phase are mixed with the basic substance to obtain a ferroelectric liquid crystal composition as a whole. Further, a compound or composition showing a phase such as a smectic C phase is used as a basic substance, and one or more compounds which are optically active but do not show a ferroelectric liquid crystal phase are mixed to form a ferroelectric liquid crystal composition as a whole. There are reports (Mol. Cryst. Liq. Cr
yst., 89, 327 (1982)). To summarize these things,
A ferroelectric liquid crystal composition is formed by mixing one or more compounds that are optically active with a compound that exhibits an achiral, smectic C phase or other phase, regardless of whether or not the compound exhibits a ferroelectric liquid crystal phase. You can see what you can do.

As described above, various compounds can be used as constituents of the liquid crystal composition, but practically, a liquid crystal exhibiting a smectic C phase or a chiral smectic C phase in a wide temperature range including room temperature. Compounds or mixtures are desirable. As the components of these smectic C liquid crystal compositions, phenylbenzoate-based liquid crystal compounds, biphenyl-based liquid crystal compounds, phenylpyrimidine-based liquid crystal compounds, and ester-based liquid crystal compounds are known. However, it cannot be said that the liquid crystal compositions containing these compounds as constituents still have sufficient properties. Therefore, at present, it is necessary to test various materials showing the smectic C phase and optimize response time, memory stability, layer structure in the smectic C phase, tilt angle, alignment characteristics on the alignment film, and the like. Has become.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a high-speed response, orientation,
Liquid crystal composition with improved properties such as high contrast ratio,
It is intended to provide a liquid crystal device using the liquid crystal composition.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found a certain kind of liquid crystal composition, and have reached the present invention. That is, the present invention provides at least one optically active naphthalene compound represented by the following general formula (1) (formula 6) and at least one non-optically active naphthalene compound represented by the following general formula (2) (formula 7) The present invention relates to a liquid crystal composition containing an active ester compound and a liquid crystal element having the liquid crystal composition disposed between a pair of electrode substrates.

[0008]

Embedded image [Wherein, R ₁ represents a linear or branched alkyl group having 3 to 24 carbon atoms, R ^* has an optically active asymmetric carbon, and may be a carbon atom which may be substituted by a halogen atom or an alkoxy group. Represents an alkyl group of Formulas 3 to 24, Y ₁ represents a single bond or a —O— group, and Y ₂ represents a —COO— group or —C
Represents an H ₂ O— group, X ₁ and X ₂ represent a halogen atom or a hydrogen atom, and n ₁ represents 0 or 1.]

[0009]

Embedded image [Wherein, R ₂ and R ₃ each represent a linear or branched alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or 3 to 24 carbon atoms which may be substituted with a halogen atom. A linear or branched unsaturated alkyl group of
A straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or
Represents a linear or branched unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, and R ₃ is a cycloalkyl group represented by the following general formula (3) Alkyl group

[0010]

Embedded image (Wherein, p represents an integer of 0 to 4, and q represents an integer of 2 to 8), and Y ₃ is a single bond, a —O— group,
OO— or —OCOO—, and X ₃ represents a hydrogen atom or a halogen atom.

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The liquid crystal composition of the present invention contains at least one optically active naphthalene compound represented by the general formula (1) and at least one non-optically active ester compound represented by the general formula (2). A liquid crystal composition comprising: In the liquid crystal composition of the present invention, the optically active naphthalene compound represented by the general formula (1) used has a value of n _{1 and} a value of Y ₂
The following general formulas (1-A) and (1-A)
B), (1-C) and (1-D) (Chem. 9).

[0012]

Embedded image

In the liquid crystal composition of the present invention, the compound represented by the general formula (1)
Each of the optically active naphthalene compounds of -A) to (1-D) may be used alone, or a plurality of them may be used in combination. When the purpose is to reduce the viscosity of the liquid crystal composition, the compound represented by the general formula (1-A) or (1-C)
It is preferred to use the compound of In the optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention, R ₁ represents a linear or branched alkyl group having 3 to 24 carbon atoms, and preferably 4 carbon atoms. ~ 2
0 represents a straight-chain or branched-chain alkyl group, more preferably a straight-chain or branched-chain alkyl group having 6 to 15 carbon atoms.

Specific examples of the group represented by R ₁ include, for example, n-propyl, n-butyl, n-pentyl,
n-hexyl group, n-heptyl group, n-octyl group, n
-Nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n
-Pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-
Eicosyl group, n-heneicosyl group, n-docosyl group,
n-tricosyl group, n-tetracosyl group, 1-methylethyl group, 1,1-dimethylethyl group, 1-methylpropyl group, 1-ethylpropyl group, 1-n-propylpropyl group, 1-methylbutyl group, 1 -Ethylbutyl group, 1-
n-propylbutyl group, 1-n-butylbutyl group, 1-
Methylpentyl group, 1-ethylpentyl group, 1-n-propylpentyl group, 1-n-butylpentyl group, 1-n
-Pentylpentyl group, 1-methylhexyl group, 1-ethylhexyl group, 1-n-propylhexyl group, 1-n
-Butylhexyl group, 1-n-pentylhexyl group, 1
-N-hexylhexyl group, 1-methylheptyl group, 1
-Ethylheptyl group, 1-n-propylheptyl group, 1
-N-butylheptyl group, 1-n-pentylheptyl group, 1-n-heptylheptyl group, 1-methyloctyl group, 1-ethyloctyl group, 1-n-propyloctyl group, 1-n-butyloctyl group , 1-n-pentyloctyl group, 1-n-hexyloctyl group, 1-n-heptyloctyl group, 1-n-octyloctyl group, 1-methylnonyl group, 1-ethylnonyl group, 1-n-propylnonyl group , 1-n-butylnonyl group, 1-n-pentylnonyl group, 1-n-hexylnonyl group, 1-n-heptylnonyl group, 1-n-octylnonyl group, 1-n-nonylnonyl group, 1-methyldecyl group ,

2-methylpropyl, 2-methylbutyl, 2-ethylbutyl, 2-methylpentyl, 2-
Ethylpentyl group, 2-n-propylpentyl group, 2-
Methylhexyl group, 2-ethylhexyl group, 2-n-propylhexyl group, 2-n-butylhexyl group, 2-methylheptyl group, 2-ethylheptyl group, 2-n-propylheptyl group, 2-n-butyl Heptyl group, 2-n-
Pentylheptyl group, 2-methyloctyl group, 2-ethyloctyl group, 2-n-propyloctyl group, 2-n-
Butyloctyl group, 2-n-pentyloctyl group, 2-
n-hexyloctyl group, 2-methylnonyl group, 2-ethylnonyl group, 2-n-propylnonyl group, 2-n-butylnonyl group, 2-n-pentylnonyl group, 2-n-hexylnonyl group, 2-n -Heptylnonyl group, 2-methyldecyl group, 2,3-dimethylbutyl group, 2,3,3-
Trimethylbutyl, 3-methylbutyl, 3-methylpentyl, 3-ethylpentyl, 4-methylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,4,4-trimethyl Pentyl group, 2,
3,3,4-tetramethylpentyl group, 3-methylhexyl group, 2,5-dimethylhexyl group, 3-ethylhexyl group, 4-ethylhexyl group, 3,5,5, -trimethylhexyl group, 4-methylhexyl And alkyl groups such as a 6-methylheptyl group, a 3,7-dimethyloctyl group and a 6-methyloctyl group.

In the optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention, R ^* has an optically active asymmetric carbon and is substituted by a halogen atom or an alkoxy group. May have 3 carbon atoms
To 24, preferably three groups represented by the following general formulas (5) to (7).

[0017]

Embedded image Wherein R _{6 to} R ₁₀ each have 1 to 15 carbon atoms which may be substituted by a halogen atom or an alkoxy group.
Represents an alkyl group of a straight or branched chain, the alkyl group may have an asymmetric carbon, and the asymmetric carbon may be optically active or non-optically active, X ₇ is fluorine atom, chlorine atom, bromine atom or a halogen atom selected from iodine atom, r, s and t are 0 to 1
Represents an integer of 0, and C ^* indicates that the carbon atom is an optically active asymmetric carbon. However, they are not the same groups as R ₆ and R ₇ ]

In the alkyl group having an optically active asymmetric carbon represented by the general formulas (5) to (7), the absolute configuration of the optically active asymmetric carbon is not particularly limited.
The (R) -configuration or the (S) -configuration may be used. The optical purity of the optically active asymmetric carbon is
The ratio of the (R) form to the (S) form is 0: 100 (100% e
e) to 45:55 (10% ee) or 55:45 (1
0% ee) to 100: 0 (100% ee) are effectively used. Specific examples of the alkyl group having an optically active asymmetric carbon represented by the general formulas (5) to (7) include, for example, the following groups. still,
The (R) -form and the (S) -form are not particularly described, but in the present invention, both optically active forms can be effectively used.

That is, 1-methylpropyl, 1-methylbutyl, 1-methylpentyl, 1-methylhexyl, 1-methylheptyl, 1-methyloctyl, 1-methylnonyl, 1-methyldecyl, 1-methylundecyl group, 1-methyldodecyl group, 2-methylbutyl group, 2-methylpentyl group, 2-methylhexyl group, 2-methylheptyl group, 2-methyloctyl group, 2
-Methylnonyl group, 2-methyldecyl group, 2-methylundecyl group, 2-methyldodecyl group, 3-methylpentyl group, 3-methylhexyl group, 3-methylheptyl group,
3-methyloctyl group, 3-methylnonyl group, 3-methyldecyl group, 3-methylundecyl group, 3-methyldodecyl group, 4-methylhexyl group, 4-methylheptyl group, 4-methyloctyl group, 4-methylnonyl Group, 4-
Methyldecyl group, 4-methylundecyl group, 4-methyldodecyl group, 5-methylheptyl group, 5-methyloctyl group, 5-methylnonyl group, 5-methyldecyl group, 5-
Methylundecyl group, 5-methyldodecyl group, 6-methyloctyl group, 6-methylnonyl group, 6-methyldecyl group, 6-methylundecyl group, 6-methyldodecyl group,
An alkyl group having an optically active asymmetric carbon such as a 7-methylnonyl group, a 7-methyldecyl group, a 7-methylundecyl group, a 7-methyldodecyl group, an 8-methyldecyl group;
Optically active groups such as fluoropropyl, 2-fluoropropyl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 1-fluoropentyl, 2-fluoropentyl, and 3-fluoropentyl; An alkyl group substituted by a halogen atom having an asymmetric carbon,

1-methoxy-2-propyl, 1-ethoxy-2-propyl, 1-propyloxy-2-propyl, 1-butyloxy-2-propyl, 1-pentyloxy-2-propyl, 1-hexyloxy-2
-Propyl group, 1-heptyloxy-2-propyl group,
1-octyloxy-2-propyl group, 1-nonyloxy-2-propyl group, 1-methoxy-3-butyl group, 1
-Ethoxy-3-butyl group, 1-propyloxy-3-
Butyl group, 1-butyloxy-3-butyl group, 1-pentyloxy-3-butyl group, 1-hexyloxy-3-
Butyl group, 1-heptyloxy-3-butyl group, 1-octyloxy-3-butyl group, 1-nonyloxy-3-
Butyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propyloxypropyl, 2-butyloxypropyl, 2-pentyloxypropyl, 2-
Hexyloxypropyl group, 2-heptyloxypropyl group, 2-octyloxypropyl group, 2-nonyloxypropyl group, 2-methoxybutyl group, 2-ethoxybutyl group, 2-propyloxybutyl group, 2-butyloxybutyl Group, 2-pentyloxybutyl group, 2-hexyloxybutyl group, 2-heptyloxybutyl group, 2-
Examples thereof include an alkyl group substituted by an alkoxy group having an optically active asymmetric carbon such as an octyloxybutyl group and a 2-nonyloxybutyl group.

In the optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention,
Y ₁ represents a single bond or a —O— group, and Y ₂ represents —COO—
Represents a group or a —CH ₂ O— group. N ₁ represents 0 or 1, and X ₁ and X ₂ represent a halogen atom or a hydrogen atom. X ₁ and X ₂ preferably represent a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom, more preferably a fluorine atom or a hydrogen atom. Also, X
The substitution positions of ₁ and X ₂ are not particularly limited, but preferably, X ₁ is ortho to Y ₁ ,
X ₂ is ortho or meta to Y ₂ .

In the liquid crystal composition of the present invention, only one kind of the optically active naphthalene compound represented by the general formula (1) may be used, or plural kinds thereof may be used. Preferably, at least two or more are used, and more preferably, at least three or more are used. When only one kind is used, it is preferable that R ^* of the optically active naphthalene compound represented by the general formula (1) has an asymmetric carbon in a bond. Further, asymmetry When using multiple also R ^* may be the same or may be different, but R ^* is a bond of the optically active naphthalene compound represented by at least one formula (1) It preferably has carbon. In addition, "R
^"* Has an asymmetric carbon in a bond" means that r, s or t is 0 in the general formula (5), (6) or (7). When a plurality of optically active naphthalene compounds are used, R ₁ of the optically active naphthalene compound represented by the general formula (1) may be the same,
It may be different.

The optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention can be produced, for example, by the following method. That is, a naphthalenecarboxylic acid (Z ₁ represents a protecting group such as a benzyl group or a tetrahydropyranyl group) represented by the general formula (8) (formula 11) and an optically active alcohol are used to formulate the general formula (9) (formula 11). )), The protective group of the naphthalene ester derivative represented by the general formula (9) is removed, and the hydroxynaphthalene derivative represented by the general formula (10) I do.
Thereafter, the hydroxynaphthalene derivative represented by the general formula (10) and the aromatic carboxylic acid represented by the general formula (11) (formula 11) are esterified to make Y _2- in the general formula (1). An optically active naphthalene that is a COO-group can be produced.

[0024]

Embedded image

In the reaction between the naphthalenecarboxylic acid represented by the general formula (8) and the optically active alcohol,
Deriving a naphthalene carboxylic acid represented by the general formula (8) into a carboxylic acid chloride derivative with a halogenating agent such as thionyl chloride or oxalyl chloride;
Then, a base (eg, triethylamine, pyridine)
A naphthalenecarboxylic acid represented by the general formula (8) and an optically active alcohol in the presence of triphenylphosphine and diethylazodicarboxylic acid (hereinafter abbreviated as DEAD). A reaction method or the like can be used.

In the reaction between the hydroxynaphthalene derivative represented by the general formula (10) and the aromatic carboxylic acid represented by the general formula (11), the aromatic carboxylic acid represented by the general formula (11) is used. Is reacted with a halogenating agent such as thionyl chloride or oxalyl chloride to form a carboxylic acid chloride derivative, and then reacted with hydroxynaphthalene represented by the general formula (10) in the presence of a base (eg, triethylamine, pyridine). Method: A hydroxynaphthalene derivative represented by the general formula (10) and an aromatic carboxylic acid represented by the general formula (11) are N,
N'-dicyclohexylcarbodiimide (hereinafter referred to as DCC
) And a catalyst (for example, 4-pyrrolidinopyridine, 4-N, N-dimethylaminopyridine).

As another method, for example, the general formula (1)
2) A hydroxynaphthalene derivative represented by the formula (12) (Z ₂ represents a protecting group such as benzyl) and a general formula (1)
Esterifying an aromatic carboxylic acid represented by formula (1) to produce an ester compound represented by formula (13) or (formula 12), and then protecting the ester compound represented by formula (13) To produce a naphthalene carboxylic acid represented by the general formula (14) (formula 12), and further by esterifying the optically active alcohol with the naphthalene carboxylic acid represented by the general formula (14), In the formula (1), a method for producing an optically active naphthalene compound in which Y ₂ is a —COO— group can be mentioned.

[0028]

Embedded image

In the reaction between the hydroxynaphthalene derivative represented by the general formula (12) and the aromatic carboxylic acid represented by the general formula (11), the aromatic carboxylic acid represented by the general formula (11) is used. Is reacted with a halogenating agent such as thionyl chloride or oxalyl chloride to form a carboxylic acid chloride derivative, and then reacted with hydroxynaphthalene represented by the general formula (12) in the presence of a base (eg, triethylamine, pyridine). A hydroxynaphthalene derivative represented by the general formula (12) and an aromatic carboxylic acid represented by the general formula (11)
CC and a catalyst (e.g., 4-pyrrolidinopyridine, 4
-N, N-dimethylaminopyridine).

In the reaction between the naphthalene carboxylic acid represented by the general formula (14) and the optically active alcohol, the naphthalene carboxylic acid represented by the general formula (14) is converted to a halogenated compound such as thionyl chloride or oxalyl chloride. A carboxylic acid chloride derivative with an agent, followed by reaction with an optically active alcohol in the presence of a base (eg, triethylamine, pyridine). In the presence of triphenylphosphine and diethylazodicarboxylic acid (hereinafter abbreviated as DEAD).

The optically active naphthalene compound represented by the general formula (1) wherein Y ₂ is represented by —CH ₂ O— is represented by the general formula (10)
The hydroxynaphthalene derivative represented by the general formula (1)
5) It can be produced by reacting a benzyl halide derivative or a benzyl alcohol derivative (L ₁ represents a halogen atom or an OH group) represented by (Chemical Formula 13) and performing an etherification reaction. The general formula (10)
And a hydroxynaphthalene derivative represented by the general formula (1)
The reaction with the benzyl halide derivative or benzyl alcohol derivative represented by 5) can be performed, for example, by the general formula (1)
5) a method of condensing a benzyl alcohol wherein L ₁ is an OH group and a hydroxynaphthalene derivative represented by the general formula (10) with a condensing agent such as DEAD in the presence of triphenylphosphine; Wherein a benzyl halide derivative wherein L ₁ is a halogen atom and a hydroxynaphthalene derivative represented by the general formula (10) are reacted in the presence of a base (eg, sodium carbonate, potassium carbonate, sodium hydride) in a polar solvent. It can be carried out by a method or the like.

[0032]

Embedded image

Specific examples of the optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention include (1) a compound having n ₁ = 0 and Y ₂ ＝ —COO— group. Is a compound shown in Table 1 (Tables 1 to 8), (2) n ₁
= 1 and Y ₂ = -COO- group, compounds shown in Table 2 (Tables 9 to 16), (3) n ₁ = 0 and Y ₂ =
The compounds of the -CH ₂ O-group, Table 3 (Table 17-2
The compound shown in 4), wherein (4) n ₁ = 1 and Y ₂ = —CH ₂ O
Examples of the compound of the group include the compounds shown in Table 4 (Tables 25 to 32). In addition, nC in the table
_{The mH2m + 1-} group represents a linear alkyl group, and m is 3 to 24.
Is an integer. The substitution position of X ₁ is ortho to Y ₁ , and the substitution position of X ₂ is meta to Y ₂ .

[0034]

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

[0037]

[Table 4]

[0038]

[Table 5]

[0039]

[Table 6]

[0040]

[Table 7]

[0041]

[Table 8]

[0042]

[Table 9]

[0043]

[Table 10]

[0044]

[Table 11]

[0045]

[Table 12]

[0046]

[Table 13]

[0047]

[Table 14]

[0048]

[Table 15]

[0049]

[Table 16]

[0050]

[Table 17]

[0051]

[Table 18]

[0052]

[Table 19] Table 3 (continued)

[0053]

[Table 20]

[0054]

[Table 21]

[0055]

[Table 22]

[0056]

[Table 23]

[0057]

[Table 24]

[0058]

[Table 25]

[0059]

[Table 26]

[0060]

[Table 27]

[0061]

[Table 28]

[0062]

[Table 29]

[0063]

[Table 30]

[0064]

[Table 31]

[0065]

[Table 32] Next, the general formula (2) used in the liquid crystal composition of the present invention.
The non-optically active ester compound represented by the formula will be described in detail.

In the non-optically active ester compound represented by the general formula (2) of the present invention, R ₂ and R ₃ are linear or branched alkyl having 3 to 24 carbon atoms which may be substituted with a halogen atom. Group, a linear or branched unsaturated alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, and 3 carbon atoms which may be substituted with a halogen atom.
-24 carbon atoms which may be substituted with a linear or branched alkoxyalkyl group or a halogen atom.
And R ₃ may be a cycloalkyl group represented by the general formula (3).

R ₂ is preferably a straight-chain or branched-chain alkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon which may be substituted with a halogen atom, or an asymmetric group which may be substituted with a halogen atom. A straight-chain or branched-chain unsaturated alkyl group having 3 to 24 carbon atoms which does not contain carbon, and 3 to 3 carbon atoms which do not contain an asymmetric carbon atom which may be substituted by a halogen atom;
A straight-chain or branched-chain alkoxyalkyl group of 24 or an unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon atom which may be substituted with a halogen atom; A straight-chain or branched C3-C24 straight-chain or branched alkyl group containing no asymmetric carbon which may be substituted, or a straight-chain or branched C3-C24 not containing an asymmetric carbon which may be substituted with an alkyl group or a halogen atom which may be substituted by a halogen atom; Represents a chain alkoxyalkyl group.

R ₃ is preferably a straight-chain or branched-chain alkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon atom which may be substituted with a halogen atom, or an asymmetric group which may be substituted with a halogen atom. A straight-chain or branched-chain unsaturated alkyl group having 3 to 24 carbon atoms which does not contain carbon, and 3 to 3 carbon atoms which do not contain an asymmetric carbon atom which may be substituted by a halogen atom;
A straight-chain or branched-chain alkoxyalkyl group of 24, an unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon atom which may be substituted with a halogen atom, or a cycloalkyl group represented by the general formula (3) Represents an alkyl group, more preferably a straight-chain or branched-chain alkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon atom which may be substituted with a halogen atom, or an asymmetric group which may be substituted with a halogen atom. It represents a straight or branched chain alkoxyalkyl group having 3 to 24 carbon atoms containing no carbon or a cycloalkyl group represented by the general formula (3). R ₂ and R ₃ preferably have 5 to 20 carbon atoms, more preferably 6 to 18 carbon atoms.
It is.

[0069] Specific examples of the group represented by R ₂ and R _3, for example, a straight or branched chain alkyl group exemplified for R _1, 2-fluoro -n- propyl group, 3-fluoro -n- Propyl group, 1,3-difluoro-n-propyl group, 2,3-difluoro-n-propyl group, 2-fluoro-n-butyl group, 3-fluoro-n-butyl group, 4-
Fluoro-n-butyl group, 3-fluoro-2-methylpropyl group, 2,3-difluoro-n-butyl group, 2,4
-Difluoro-n-butyl group, 3,4-difluoro-n
-Butyl group, 2-fluoro-n-pentyl group, 3-fluoro-n-pentyl group, 5-fluoro-n-pentyl group, 2,4-difluoro-n-pentyl group, 2,5-difluoro-n- Pentyl group, 2-fluoro-3-methylbutyl group, 2-fluoro-n-hexyl group, 3-fluoro-n-hexyl group, 4-fluoro-n-hexyl group,
5-fluoro-n-hexyl group, 6-fluoro-n-hexyl group, 2-fluoro-n-heptyl group, 4-fluoro-n-heptyl group, 5-fluoro-n-heptyl group,
2-fluoro-n-octyl group, 3-fluoro-n-octyl group, 6-fluoro-n-octyl group, 4-fluoro-n-nonyl group, 7-fluoro-n-nonyl group, 3-
Fluoro-n-decyl group, 6-fluoro-n-decyl group, 4-fluoro-n-dodecyl group, 8-fluoro-n
-Dodecyl group, 5-fluoro-n-tetradecyl group, 9
-Fluoro-n-tetradecyl group,

2-chloro-n-propyl, 3-chloro-n-propyl, 2-chloro-n-butyl, 4-chloro-n-butyl, 2-chloro-n-pentyl, 5
-Chloro-n-pentyl group, 5-chloro-n-hexyl group, 4-chloro-n-heptyl group, 6-chloro-n-octyl group, 7-chloro-n-nonyl group, 3-chloro-n
-Decyl group, 8-chloro-n-dodecyl group, n-perfluoropropyl group, n-perfluorobutyl group, n-perfluoropentyl group, n-perfluorohexyl group,
n-perfluoroheptyl group, n-perfluorooctyl group, n-perfluorononyl group, n-perfluorodecyl group, n-perfluoroundecyl group, n-perfluorododecyl group, n-perfluorotetradecyl group , 1
-Hydro-n-perfluoropropyl group, 1-hydro-
n-perfluorobutyl group, 1-hydro-n-perfluoropentyl group, 1-hydro-n-perfluorohexyl group, 1-hydro-n-perfluoroheptyl group, 1-
Hydro-n-perfluorooctyl group, 1-hydro-n
-Perfluorononyl group, 1-hydro-n-perfluorodecyl group, 1-hydro-n-perfluoroundecyl group, 1-hydro-n-perfluorododecyl group, 1-hydro-n-perfluorotetradecyl Group, 1,1-dihydro-n-perfluoropropyl group, 1,1-dihydro-n-perfluorobutyl group, 1,1-dihydro-n-
Perfluoropentyl group, 1,1-dihydro-3-pentafluoroethyl perfluoropentyl group, 1,1-dihydro-n-perfluorohexyl group, 1,1-dihydro-n-perfluoroheptyl group, 1,1 -Dihydro-
n-perfluorooctyl group, 1,1-dihydro-n-
Perfluorononyl group, 1,1-dihydro-n-perfluorodecyl group, 1,1-dihydro-n-perfluoroundecyl group, 1,1-dihydro-n-perfluorododecyl group, 1,1-dihydro -N-perfluorotetradecyl group, 1,1-dihydro-n-perfluoropentadecyl group, 1,1-dihydro-n-perfluorohexadecyl group,

1,1,3-trihydro-n-perfluorobutyl, 1,1,3-trihydro-n-perfluorobutyl, 1,1,4-trihydro-n-perfluorobutyl, 1,4-trihydro-n-perfluoropentyl group, 1,1,5-trihydro-n-perfluoropentyl group, 1,1,3-trihydro-n-perfluorohexyl group, 1,1,6-trihydro -N-perfluorohexyl group, 1,1,5-trihydro-n-
Perfluoroheptyl group, 1,1,7-trihydro-n
-Perfluoroheptyl group, 1,1,8-trihydro-
n-perfluorooctyl group, 1,1,9-trihydro-n-perfluorononyl group, 1,1,11-trihydro-n-perfluoroundecyl group, 2- (perfluoroethyl) ethyl group, 2- (N-perfluoropropyl) ethyl group, 2- (n-perfluorobutyl) ethyl group, 2- (n-perfluoropentyl) ethyl group, 2-
(N-perfluorohexyl) ethyl group, 2- (n-perfluoroheptyl) ethyl group, 2- (n-perfluorooctyl) ethyl group, 2- (n-perfluorodecyl) ethyl group, 2- (n -Perfluorononyl) ethyl group, 2- (n-perfluorododecyl) ethyl group, 2-
(Perfluoro-9′-methyldecyl) ethyl group, 2-
Trifluoromethylpropyl group, 3- (n-perfluoropropyl) propyl group, 3- (n-perfluorobutyl) propyl group, 3- (n-perfluorohexyl) propyl group, 3- (n-perfluoroheptyl) ) Propyl group, 3- (n-perfluorooctyl) propyl group, 3
-(N-perfluorodecyl) propyl group, 3- (n-
Perfluorododecyl) propyl group,

4- (perfluoroethyl) butyl group, 4
-(N-perfluoropropyl) butyl group, 4- (n-
Perfluorobutyl) butyl, 4- (n-perfluoropentyl) butyl, 4- (n-perfluorohexyl) butyl, 4- (n-perfluoroheptyl) butyl, 4- (n-perfluoro Octyl) butyl group, 4
-(N-perfluorodecyl) butyl group, 4- (perfluoroisopropyl) butyl group, 5- (n-perfluoropropyl) pentyl group, 5- (n-perfluorobutyl) pentyl group, 5- (n- Perfluoropentyl) pentyl group, 5- (n-perfluorohexyl) pentyl group, 5- (n-perfluoroheptyl) pentyl group, 5
-(N-perfluorooctyl) pentyl group, 6- (perfluoroethyl) hexyl group, 6- (n-perfluoropropyl) hexyl group, 6- (n-perfluorobutyl) hexyl group, 6- (n- Perfluorohexyl) hexyl group, 6- (n-perfluoroheptyl) hexyl group, 6- (n-perfluorooctyl) hexyl group, 6
-(Perfluoroisopropyl) hexyl group, 6- (perfluoro-7'-methyloctyl) hexyl group, 7-
Substituted with a halogen atom such as a (perfluoroethyl) heptyl group, a 7- (n-perfluoropropyl) heptyl group, a 7- (n-perfluorobutyl) heptyl group, or a 7- (n-perfluoropentyl) heptyl group. Alkyl group,

2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 5-methoxypentyl, 6-methoxyhexyl, 7-methoxyheptyl, 8-methoxyoctyl, 9-methoxynonyl ,
10-methoxydecyl group, ethoxymethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 5-ethoxypentyl group, 6-ethoxyhexyl group, 7-ethoxyheptyl group, 8-ethoxyoctyl Group, 9-ethoxynonyl group, 10-ethoxydecyl group, n-propyloxymethyl group, 2-n-propyloxyethyl group, 3-n-propyloxypropyl group,
-N-propyloxybutyl group, 5-n-propyloxypentyl group, 6-n-propyloxyhexyl group, 7
-N-propyloxyheptyl group, 8-n-propyloxyoctyl group, 9-n-propyloxynonyl group, 1
0-n-propyloxydecyl group, n-butyloxymethyl group, 2-n-butyloxyethyl group, 3-n-butyloxypropyl group, 4-n-butyloxybutyl group,
5-n-butyloxypentyl group, 6-n-butyloxyhexyl group, 7-n-butyloxyheptyl group, 8-
n-butyloxyoctyl group, 9-n-butyloxynonyl group, 10-n-butyloxydecyl group, n-pentyloxymethyl group, 2-n-pentyloxyethyl group,
3-n-pentyloxypropyl group, 4-n-pentyloxybutyl group, 5-n-pentyloxypentyl group,
6-n-pentyloxyhexyl group, 7-n-pentyloxyheptyl group, 8-n-pentyloxyoctyl group, 9-n-pentyloxynonyl group, 10-n-pentyloxydecyl group, n-hexyloxymethyl Group, 2
-N-hexyloxyethyl group, 3-n-hexyloxypropyl group, 4-n-hexyloxybutyl group, 5-
n-hexyloxypentyl group, 6-n-hexyloxyhexyl group, 7-n-hexyloxyheptyl group, 8
-N-hexyloxyoctyl group, 9-n-hexyloxynonyl group, 10-n-hexyloxydecyl group, n
-Heptyloxymethyl group, 2-n-heptyloxyethyl group, 3-n-heptyloxypropyl group, 4-n-
Heptyloxybutyl group, 5-n-heptyloxypentyl group, 6-n-heptyloxyhexyl group, 7-n-
Heptyloxyheptyl group, 8-n-heptyloxyoctyl group, 9-n-heptyloxynonyl group, 10-n
A heptyloxydecyl group,

Octyloxymethyl group, 2-n-octyloxyethyl group, 3-n-octyloxypropyl group, 4-n-octyloxybutyl group, 5-n-octyloxypentyl group, 6-n-octyloxy Hexyl group, 7-n-octyloxyheptyl group, 8-n-octyloxyoctyl group, 9-n-octyloxynonyl group, 10-n-octyloxydecyl group, n-nonyloxymethyl group, 2-n- Nonyloxyethyl group, 3-n
-Nonyloxypropyl group, 4-n-nonyloxybutyl group, 5-n-nonyloxypentyl group, 6-n-nonyloxyhexyl group, 7-n-nonyloxyheptyl group, 8-n-nonyloxyoctyl group , 9-n-nonyloxynonyl group, 10-n-nonyloxydecyl group, n
-Decyloxymethyl group, 2-n-decyloxyethyl group, 3-n-decyloxypropyl group, 4-n-decyloxybutyl group, 5-n-decyloxypentyl group, 6
-N-decyloxyhexyl group, 7-n-decyloxyheptyl group, 8-n-decyloxyoctyl group, 9-n
-Decyloxynonyl group, 10-n-decyloxydecyl group, 2-n-undecyloxyethyl group, 4-n-undecyloxybutyl group, 6-n-undecyloxyhexyl group, 8-n-un Decyloxyoctyl group, 10
-N-undecyloxydecyl group, 2-n-dodecyloxyethyl group, 4-n-dodecyloxybutyl group, 6-
n-dodecyloxyhexyl group, 8-n-dodecyloxyoctyl group, 10-n-dodecyloxydecyl group, 1
-Methyl-2-methoxyethyl group, 1-methyl-2-ethoxyethyl group, 1-methyl-2-n-propyloxyethyl group, 1-methyl-2-n-butyloxyethyl group, 1-methyl-2 -N-pentyloxyethyl group, 1
-Methyl-2-n-hexyloxyethyl group, 1-methyl-2-n-heptyloxyethyl group, 1-methyl-2
-N-octyloxyethyl group, 1-methyl-2-n-
Nonyloxyethyl group, 1-methyl-2-n-decyloxyethyl group, 1-methyl-2-n-undecyloxyethyl group, 1-methyl-2-n-dodecyloxyethyl group,

2-methoxypropyl, 2-ethoxypropyl, 2-n-propyloxypropyl, 2-n
-Butyloxypropyl group, 2-n-pentyloxypropyl group, 2-n-hexyloxypropyl group, 2-n
-Heptyloxypropyl group, 2-n-octyloxypropyl group, 2-n-nonyloxypropyl group, 2-n
-Decyloxypropyl group, 2-n-undecyloxypropyl group, 2-n-dodecyloxypropyl group, 1-
Methyl-3-methoxypropyl group, 1-methyl-3-ethoxypropyl group, 1-methyl-3-n-propyloxypropyl group, 1-methyl-3-n-butyloxypropyl group, 1-methyl-3- n-pentyloxypropyl group, 1-methyl-3-n-hexyloxypropyl group,
1-methyl-3-n-heptyloxypropyl group, 1-
Methyl-3-n-octyloxypropyl group, 1-methyl-3-n-nonyloxypropyl group, 1-methyl-3
-N-decyloxypropyl group, 1-methyl-3-n-
Undecyloxypropyl group, 1-methyl-3-n-dodecyloxypropyl group, 3-methoxybutyl group, 3-
Ethoxybutyl group, 3-n-propyloxybutyl group,
3-n-butyloxybutyl group, 3-n-pentyloxybutyl group, 3-n-hexyloxybutyl group, 3-n
-Heptyloxybutyl group, 3-n-octyloxybutyl group, 3-n-nonyloxybutyl group, 3-n-decyloxybutyl group, 3-n-undecyloxybutyl group, 3-n-dodecyloxybutyl Group, isopropyloxymethyl group, 2-isopropyloxyethyl group, 3-
Isopropyloxypropyl group, 4-isopropyloxybutyl group, 5-isopropyloxypentyl group, 6-
Isopropyloxyhexyl group, 7-isopropyloxyheptyl group, 8-isopropyloxyoctyl group, 9
-Isopropyloxynonyl group, 10-isopropyloxydecyl group, isobutyloxymethyl group, 2-isobutyloxyethyl group, 3-isobutyloxypropyl group, 4-isobutyloxybutyl group, 5-isobutyloxypentyl group, 6-isobutyloxy Hexyl group, 7
-Isobutyloxyheptyl group, 8-isobutyloxyoctyl group, 9-isobutyloxynonyl group, 10-isobutyloxydecyl group, tert-butyloxymethyl group, 2-tert-butyloxyethyl group, 3-tert-butyloxypropyl Group, 4-tert-butyloxybutyl group, 5-tert-butyloxypentyl group, 6-tert-butyloxyhexyl group, 7-tert-butyloxyheptyl group, 8-tert-butyloxyoctyl group, 9-tert −
Butyloxynonyl group, 10-tert-butyloxydecyl group,

(2-ethylbutyloxy) methyl group, 2
-(2'-ethylbutyloxy) ethyl group, 3- (2 '
-Ethylbutyloxy) propyl group, 4- (2'-ethylbutyloxy) butyl group, 5- (2'-ethylbutyloxy) pentyl group, 6- (2'-ethylbutyloxy) hexyl group, 7- ( 2′-ethylbutyloxy) heptyl group, 8- (2′-ethylbutyloxy) octyl group, 9- (2′-ethylbutyloxy) nonyl group, 10
-(2'-ethylbutyloxy) decyl group, (3-ethylpentyloxy) methyl group, 2- (3'-ethylpentyloxy) ethyl group, 3- (3'-ethylpentyloxy) propyl group, 4- A (3′-ethylpentyloxy) butyl group, a 5- (3′-ethylpentyloxy) pentyl group, a 6- (3′-ethylpentyloxy) hexyl group, a 7- (3′-ethylpentyloxy) heptyl group, 8- (3′-ethylpentyloxy) octyl group,
9- (3′-ethylpentyloxy) nonyl group, 10-
(3′-ethylpentyloxy) decyl group, 6- (1 ′
-Methyl-n-heptyloxy) hexyl group, 4-
(1′-methyl-n-heptyloxy) butyl group, 2-
(2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-propyloxyethoxy) ethyl group, 2- (2′-isopropyloxyethoxy) ethyl group, 2- (2'-n-butyloxyethoxy) ethyl group, 2- (2'-isobutyloxyethoxy) ethyl group, 2- (2'-tert-butyloxyethoxy) ethyl group, 2- (2'-n -Pentyloxyethoxy) ethyl group, 2- [2 '-(2 "-ethylbutyloxy) ethoxy] ethyl group, 2- (2'-n-hexyloxyethoxy) ethyl group, 2- [2'-(3 "
-Ethylpentyloxy) ethoxy] ethyl group, 2-
(2′-n-heptyloxyethoxy) ethyl group, 2-
(2′-n-octyloxyethoxy) ethyl group, 2-
(2′-n-nonyloxyethoxy) ethyl group, 2-
(2′-n-decyloxyethoxy) ethyl group, 2-
(2′-n-undecyloxyethoxy) ethyl group, 2
A-(2'-n-dodecyloxyethoxy) ethyl group,

2- [2 '-(2 "-methoxyethoxy)
Ethoxy] ethyl group, 2- [2 '-(2 "-ethoxyethoxy) ethoxy] ethyl group, 2- [2'-(2" -n
-Propyloxyethoxy) ethoxy] ethyl group, 2-
[2 '-(2 "-isopropyloxyethoxy) ethoxy] ethyl group, 2- [2'-(2" -n-butyloxyethoxy) ethoxy] ethyl group, 2- [2 '-(2 "-
Isobutyloxyethoxy) ethoxy] ethyl group, 2-
[2 ′-(2 ″ -tert-butyloxyethoxy) ethoxy] ethyl group, 2- {2 ′-[2 ″-(2 ′ ″-ethylbutyloxy) ethoxy] ethoxy} ethyl group, 2-
[2 '-(2 "-n-pentyloxyethoxy) ethoxy] ethyl group, 2- [2'-(2" -n-hexyloxyethoxy) ethoxy] ethyl group, 2- {2 '-[2 "
-(3 "'-ethylpentyloxy) ethoxy] ethoxydiethyl group, 2- [2'-(2" -n-heptyloxyethoxy) ethoxy] ethyl group, 2- [2 '-(2 "
-N-octyloxyethoxy) ethoxy] ethyl group,
2- [2 '-(2 "-n-nonyloxyethoxy) ethoxy] ethyl group, 2- [2'-(2" -n-decyloxyethoxy) ethoxy] ethyl group, 2- [2 '-(2 "
-N-undecyloxyethoxy) ethoxy] ethyl group, 2- [2 '-(2 "-n-dodecyloxyethoxy) ethoxy] ethyl group, 2- {2'-[2"-
(2 ″ ′-methoxyethoxy) ethoxy] ethoxy} ethyl group, 2- {2 ′-[2 ″-(2 ′ ″-n-dodecyloxyethoxy) ethoxy] ethoxy} ethyl group, 2-
｛2 '-｛2 "-[2"'-(2-methoxyethoxy)
Ethoxy] ethoxy {ethoxy} ethyl group, 2- {2 ′
− ｛2 ″ − ｛2 ′ ″ − [2- (2-methoxyethoxy)
Ethoxy) ethoxy-ethoxy-ethoxy-ethyl group,

1-methyl-2- (1'-methyl-2'-
Methoxyethoxy) ethyl group, 1-methyl-2- (1 ′
-Methyl-2'-ethoxyethoxy) ethyl group, 1-methyl-2- (1'-methyl-2'-n-propyloxyethoxy) ethyl group, 1-methyl-2- (1'-methyl-2 ' -Isopropyloxyethoxy) ethyl group, 1-
Methyl-2- (1′-methyl-2′-n-butyloxyethoxy) ethyl group, 1-methyl-2- (1′-methyl-2′-isobutyloxyethoxy) ethyl group, 1-methyl-2- (1′-methyl-2′-tert-butyloxyethoxy) ethyl group, 1-methyl-2- (1′-methyl-2′-n-pentyloxyethoxy) ethyl group, 1-
Methyl-2- (1′-methyl-2′-n-hexyloxyethoxy) ethyl group, 1-methyl-2- (1′-methyl-2′-n-heptyloxyethoxy) ethyl group, 1
-Methyl-2- (1'-methyl-2'-n-octyloxyethoxy) ethyl group, 1-methyl-2- (1'-methyl-2'-n-nonyloxyethoxy) ethyl group,
-Methyl-2- (1′-methyl-2′-n-decyloxyethoxy) ethyl group, 1-methyl-2- (1′-methyl-2′-n-undecyloxyethoxy) ethyl group,
1-methyl-2- (1′-methyl-2′-n-dodecyloxyethoxy) ethyl group,

1-methyl-2- [1'-methyl-2'-
(1 "-methyl-2" -methoxyethoxy) ethoxy]
Ethyl group, 1-methyl-2- [1′-methyl-2′-
(1 "-methyl-2" -ethoxyethoxy) ethoxy]
Ethyl group, 1-methyl-2- [1′-methyl-2′-
(1 "-methyl-2" -n-propyloxyethoxy)
Ethoxy] ethyl group, 1-methyl-2- [1′-methyl-2 ′-(1 ″ -methyl-2 ″ -isopropyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1 ′
-Methyl-2 '-(1 "-methyl-2" -n-butyloxyethoxy) ethoxy] ethyl group, 1-methyl-2-
[1'-methyl-2 '-(1 "-methyl-2" -isobutyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2'-(1 "-methyl-2") −
tert-butyloxyethoxy) ethoxy] ethyl group, 1
-Methyl-2- [1'-methyl-2 '-(1 "-methyl-2" -n-pentyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2'-( 1 "
-Methyl-2 "-n-hexyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2 '
-(1 "-methyl-2" -n-heptyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2 '-(1 "-methyl-2" -n-octyloxyethoxy) ) Ethoxy] ethyl group, 1-methyl-2-
[1'-methyl-2 '-(1 "-methyl-2" -n-nonyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2'-(1 "-methyl- 2 "-
n-decyloxyethoxy) ethoxy] ethyl group, 1-
Methyl-2- [1′-methyl-2 ′-(1 ″ -methyl-
2 "-n-undecyloxyethoxy) ethoxy] ethyl group, 1-methyl-2- [1'-methyl-2 '-(1"
-Methyl-2 "-n-dodecyloxyethoxy) ethoxy] ethyl group,

2-ethoxyethoxymethyl group, 2-n-
Butyloxyethoxymethyl group, 2-n-hexyloxyethoxymethyl group, 3-ethoxypropyloxymethyl group, 3-n-propyloxypropyloxymethyl group, 3-n-pentyloxypropyloxymethyl group,
3-n-hexyloxypropyloxymethyl group, 2-
Methoxy-1-methylethoxymethyl group, 2-ethoxy-1-methylethoxymethyl group, 2-n-butyloxy-1-methylethoxymethyl group, 4-methoxybutyloxymethyl group, 4-ethoxybutyloxymethyl group, 4
-N-butyloxybutyloxymethyl group, 2- (3 ′
-Methoxypropyloxy) ethyl group, 2- (3'-ethoxypropyloxy) ethyl group, 2- (1'-methyl-2'-methoxyethoxy) ethyl group, 2- (1'-methyl-2'-ethoxy) Ethoxy) ethyl group, 2- (1 ′
-Methyl-2'-n-butyloxyethoxy) ethyl group, 2- (4'-methoxybutyloxy) ethyl group, 2
-(4'-ethoxybutyloxy) ethyl group, 2-
[4 '-(2 "-ethylbutyloxy) butyloxy]
Ethyl group, 2- [4 '-(3 "-ethylpentyloxy) butyloxy] ethyl group, 3- (2'-methoxyethoxy) propyl group, 3- (2'-ethoxyethoxy)
Propyl group, 3- (2′-n-pentyloxyethoxy) propyl group, 3- (2′-n-hexyloxyethoxy) propyl group, 3- (3′-ethoxypropyloxy) propyl group, 3- (3 '-N-propyloxypropyloxy) propyl group, 3- (3'-n-butyloxypropyloxy) propyl group, 3- (4'-ethoxybutyloxy) propyl group, 3- (5'-ethoxypentyloxy ) Propyl, 4- (2′-methoxyethoxy) butyl, 4- (2′-ethoxyethoxy) butyl, 4- (2′-isopropyloxyethoxy) butyl, 4- (2′-isobutyloxyethoxy) ) Butyl group, 4- (2′-n-butyloxyethoxy) butyl group, 4- (2′-n-hexyloxyethoxy) butyl group, 4- (3′-n-propyloxypropyl) Oxy)
Butyl group, 4- (2'-n-propyloxy-1'-methylethoxy) butyl group, 4- [2 '-(2 "-methoxyethoxy) ethoxy] butyl group, 4- [2'-(2"
-N-butyloxyethoxy) ethoxy] butyl group, 4
-[2 '-(2 "-n-hexyloxyethoxy) ethoxy] butyl group, 5- (2'-n-hexyloxyethoxy) pentyl group, 2- [2'-(2" -n-butyloxyethoxy) ) Ethoxy] ethyl;

(2-ethylhexyloxy) methyl group,
(3,5,5-trimethylhexyloxy) methyl group,
(3,7-dimethyloctyloxy) methyl group, 2-
(2′-ethylhexyloxy) ethyl group, 2-
(3 ′, 5 ′, 5′-trimethylhexyloxy) ethyl group, 2- (3 ′, 7′-dimethyloctyloxy) ethyl group, 3- (2′-ethylhexyloxy) propyl group, 3- (3 ′ , 5 ', 5'-trimethylhexyloxy) propyl group, 3- (3', 7'-dimethyloctyloxy) propyl group, 4- (2'-ethylhexyloxy) butyl group, 4- (3 ', 5' , 5'-trimethylhexyloxy) butyl group, 4- (3 ', 7'-dimethyloctyloxy) butyl group, 5- (2'-ethylhexyloxy) pentyl group, 5- (3', 5 ', 5' -Trimethylhexyloxy) pentyl group, 5- (3 ', 7'
-Dimethyloctyloxy) pentyl group, 6- (2'-
Ethylhexyloxy) hexyl group, 6- (3 ′,
5 ′, 5′-trimethylhexyloxy) hexyl group,
Alkoxyalkyl groups such as 6- (3 ′, 7′-dimethyloctyloxy) hexyl group, 2- (2′-trifluoromethylpropyloxy) ethyl group, 4- (2′-trifluoromethylpropyloxy) butyl group , 6- (2 '
-Trifluoromethylpropyloxy) hexyl group, 8
-(2'-trifluoromethylpropyloxy) octyl group, 2- (2'-trifluoromethylbutyloxy)
Ethyl group, 4- (2′-trifluoromethylbutyloxy) butyl group, 6- (2′-trifluoromethylbutyloxy) hexyl group, 8- (2′-trifluoromethylbutyloxy) octyl group, 2- (2′-trifluoromethylheptyloxy) ethyl group, 4- (2′-trifluoromethylheptyloxy) butyl group, 6- (2′-
Trifluoromethylheptyloxy) hexyl group, 8-
(2′-trifluoromethylheptyloxy) octyl group, 2- (2′-fluoroethyloxy) ethyl group, 4
-(2'-fluoroethyloxy) butyl group, 6-
(2′-fluoroethyloxy) hexyl group, 8-
(2′-fluoroethyloxy) octyl group, 2-
(2′-fluoro-n-propyloxy) ethyl group, 4
A-(2'-fluoro-n-propyloxy) butyl group,
6- (2′-fluoro-n-propyloxy) hexyl group, 8- (2′-fluoro-n-propyloxy) octyl group, 2- (3′-fluoro-n-propyloxy)
Ethyl group, 4- (3'-fluoro-n-propyloxy) butyl group, 6- (3'-fluoro-n-propyloxy) hexyl group, 8- (3'-fluoro-n-propyloxy) octyl group , 2- (3'-fluoro-2'-
Methylpropyloxy) ethyl group, 4- (3′-fluoro-2′-methylpropyloxy) butyl group, 6-
(3'-fluoro-2'-methylpropyloxy) hexyl group, 8- (3'-fluoro-2'-methylpropyloxy) octyl group, 2- (2 ', 3'-difluoro-
n-propyloxy) ethyl group, 4- (2 ′, 3′-difluoro-n-propyloxy) butyl group, 6-
(2 ′, 3′-difluoro-n-propyloxy) hexyl group, 8- (2 ′, 3′-difluoro-n-propyloxy) octyl group, 2- (2′-fluoro-n-butyloxy) ethyl group 4- (2′-fluoro-n-butyloxy) butyl group, 6- (2′-fluoro-n-butyloxy) hexyl group, 8- (2′-fluoro-n-butyloxy) octyl group, 2- (3 '-Fluoro-n-
Butyloxy) ethyl group, 4- (3′-fluoro-n-
Butyloxy) butyl group, 6- (3′-fluoro-n-
Butyloxy) hexyl group, 8- (3′-fluoro-n
-Butyloxy) octyl group, 2- (4′-fluoro-
n-butyloxy) ethyl group, 4- (4′-fluoro-
n-butyloxy) butyl group, 6- (4′-fluoro-
n-butyloxy) hexyl group, 8- (4′-fluoro-n-butyloxy) octyl group, 2- (2 ′, 3′-
Difluoro-n-butyloxy) ethyl group, 4-
(2 ′, 3′-difluoro-n-butyloxy) butyl group, 6- (2 ′, 3′-difluoro-n-butyloxy) hexyl group, 8- (2 ′, 3′-difluoro-n-)
Butyloxy) octyl group, perfluoro (2-n-hexyloxyethyl) group,

A 1,1-dihydro-perfluoro (2-methoxyethyl) group, a 1,1-dihydro-perfluoro (3-n-propyloxypropyl) group, a 1,1-dihydro-perfluoro (2-ethoxy) group Ethyl) group, 1,1
-Dihydro-perfluoro (2-n-pentyloxyethyl) group, 2- (2'-n-perfluorobutyloxyethoxy) ethyl group, 3- (n-perfluorobutyloxy) -3,3-difluoroethyl Group, 4- (1,1,
7-trihydro-n-perfluoroheptyloxy) butyl group, 2- (n-perfluoropropyloxy) -2
-Trifluoromethyl-2-fluoroethyl group, 2-
(2′-trichloromethylpropyloxy) ethyl group,
4- (2'-trichloromethylpropyloxy) butyl group, 6- (2'-trichloromethylpropyloxy) hexyl group, 8- (2'-trichloromethylpropyloxy) octyl group, 2- (2'-trichloromethyl Butyloxy) ethyl group, 4- (2′-trichloromethylbutyloxy) butyl group, 6- (2′-trichloromethylbutyloxy) hexyl group, 8- (2′-trichloromethylbutyloxy) octyl group, 2- (2′-trichloromethylheptyloxy) ethyl group, 4- (2′-trichloromethylheptyloxy) butyl group, 6- (2′-trichloromethylheptyloxy) hexyl group, 8-
(2′-trichloromethylheptyloxy) octyl group, 2- (2′-chloroethoxy) ethyl group, 4-
(2'-chloroethoxy) butyl group, 6- (2'-chloroethoxy) hexyl group, 8- (2'-chloroethoxy) octyl group, 2- (2'-chloro-n-propyloxy) ethyl group, 4- (2′-chloro-n-propyloxy) butyl group, 6- (2′-chloro-n-propyloxy) hexyl group, 8- (2′-chloro-n-propyloxy) octyl group, 2- (3 '-Chloro-n-propyloxy) ethyl group, 4- (3'-chloro-n-propyloxy) butyl group, 6- (3'-chloro-n-propyloxy) hexyl group, 8- (3'- Chloro-n-propyloxy) octyl group, 2- (3′-chloro-2′-
Methylpropyloxy) ethyl group, 4- (3′-chloro-2′-methylpropyloxy) butyl group, 6- (3 ′
-Chloro-2'-methylpropyloxy) hexyl group,
8- (3′-chloro-2′-methylpropyloxy) octyl group, 2- (2 ′, 3′-dichloro-n-propyloxy) ethyl group, 4- (2 ′, 3′-dichloro-n-)
Propyloxy) butyl group, 6- (2 ′, 3′-dichloro-n-propyloxy) hexyl group, 8- (2 ′,
3′-dichloro-n-propyloxy) octyl group, 2
-(2'-chloro-n-butyloxy) ethyl group, 4-
(2′-chloro-n-butyloxy) butyl group, 6-
(2′-chloro-n-butyloxy) hexyl group, 8-
(2′-chloro-n-butyloxy) octyl group, 2-
(3′-chloro-n-butyloxy) ethyl group, 4-
(3′-chloro-n-butyloxy) butyl group, 6-
(3′-chloro-n-butyloxy) hexyl group, 8-
(3′-chloro-n-butyloxy) octyl group, 2-
(4′-chloro-n-butyloxy) ethyl group, 4-
(4′-chloro-n-butyloxy) butyl group, 6-
(4′-chloro-n-butyloxy) hexyl group, 8-
(4′-chloro-n-butyloxy) octyl group, 2-
(2 ′, 3′-dichloro-n-butyloxy) ethyl group, 4- (2 ′, 3′-dichloro-n-butyloxy)
Butyl group, 6- (2 ′, 3′-dichloro-n-butyloxy) hexyl group, 8- (2 ′, 3′-dichloro-n-)
An alkoxyalkyl group substituted by a halogen atom such as butyloxy) octyl group,

2-propenyloxymethyl group, 2-
(2′-propenyloxy) ethyl group, 2- [2′-
(2 "-propenyloxy) ethoxy] ethyl group, 3-
(2′-propenyloxy) propyl group, 4- (2′-
Propenyloxy) butyl group, 5- (2′-propenyloxy) pentyl group, 6- (2′-propenyloxy)
Hexyl group, 7- (2′-propenyloxy) heptyl group, 8- (2′-propenyloxy) octyl group, 9-
(2′-propenyloxy) nonyl group, 10- (2′-
Unsaturated alkoxyalkyl groups such as propenyloxy) decyl group, 2- (2′-propenyloxy) -perfluoroethyl group, 3- (2′-propenyloxy) -perfluoropropyl group, 4- (2′-propenyl) Oxy)-
A perfluorobutyl group, a 5- (2′-propenyloxy) -perfluoropentyl group, a 6- (2′-propenyloxy) -perfluorohexyl group, a 7- (2′-propenyloxy) -perfluoroheptyl group, 8-
(2'-propenyloxy) -unsaturated alkoxyalkyl group substituted with a halogen atom such as perfluorooctyl group, 3-n-perfluoropropyl-2-propenyl group, 3-n-perfluorobutyl-2-propenyl Group,
3-n-perfluoropentyl-2-propenyl group, 3
-N-perfluorohexyl-2-propenyl group, 3-
n-perfluoroheptyl-2-propenyl group, 3-n
An unsaturated alkyl group substituted with a halogen atom such as -perfluorooctyl-2-propenyl group,

2-propenyl group, 2-butenyl group, 3-
Butenyl group, 2-pentenyl group, 3-pentenyl group, 4
-Pentenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 3-heptenyl, 4-heptenyl group, 5-heptenyl group, 6-heptenyl, 2-octenyl Group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6
-Octenyl group, 7-octenyl group, 2-nonenyl group,
3-nonenyl group, 4-nonenyl group, 5-nonenyl group, 6
-Nonenyl group, 7-nonenyl group, 8-nonenyl group, 2-
Decenyl group, 3-decenyl group, 4-decenyl group, 5-decenyl group, 6-decenyl group, 7-decenyl group, 8-decenyl group, 9-decenyl group, 2-butynyl group, 3-hexynyl group, 3- Heptynyl group, 4-heptynyl group, 5-heptynyl group, 7-octynyl group, 3,7-dimethyl-6
And unsaturated alkyl groups such as -octenyl group.

Specific examples of the cycloalkyl group represented by the general formula (3) include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, and cyclopropylmethyl. Group, cyclobutylmethyl group, cyclopentylmethyl group, cycloheptylmethyl group, cyclooctylmethyl group, cyclononylmethyl group, 2-cyclopropylethyl group, 2-cyclobutylethyl group, 2-cyclopentylethyl group, 2-cyclohexylethyl Group, 2-
Cycloheptylethyl group, 2-cyclooctylethyl group, 2-cyclononylethyl group, 3-cyclopropylpropyl group, 3-cyclobutylpropyl group, 3-cyclopentylpropyl group, 3-cyclohexylpropyl group, 3
-Cycloheptylpropyl group, 3-cyclooctylpropyl group, 3-cyclononylpropyl group, 4-cyclopropylbutyl group, 4-cyclobutylbutyl group, 4-cyclopentylbutyl group, 4-cyclohexylbutyl group, 4-
Examples thereof include cycloalkyl groups such as a cycloheptylbutyl group, a 4-cyclooctylbutyl group, and a 4-cyclononylbutyl group.

The liquid crystal composition of the present invention has the general formula (2)
As the non-optically active ester compound represented by the formula (1), only one kind may be used, or a plurality of kinds may be used. When a plurality of non-optically active ester compounds represented by the general formula (2) are used in the liquid crystal composition of the present invention, the non-optically active ester compound represented by each of the general formulas (2) has R
₂ and / or R ₃ may be the same or different. In the non-optically active ester compound represented by the general formula (2) of the present invention, Y ₃ is a single bond, —O
—, —COO—, or —OCOO—, and preferably represents —O—, —COO—, or —OCOO—. Further, X ₃ represents a hydrogen atom or a halogen atom, and the substitution position of X ₃ is ortho or meta position with respect to Y _3, and preferably, ortho to Y _3.

The non-optically active ester compound of the present invention represented by the general formula (2) can be produced, for example, through the following steps. That is, the general formula (16)
An ester compound represented by the general formula (17) (Formula 14) is produced from the carboxylic acid represented by the formula (4) and a desired alcohol, and this compound is reduced to obtain a non-optical compound represented by the general formula (2). An active ester compound can be produced, and it can also be produced by a method of reacting a carboxylic acid compound represented by the general formula (18) with a desired alcohol. The reaction between the carboxylic acid represented by the general formula (16) and a desired alcohol is carried out by converting the carboxylic acid represented by the general formula (16) into a carboxylic acid by using a halogenating agent such as thionyl chloride or oxalyl chloride. A method of reacting a desired derivative with a desired alcohol in the presence of a base (eg, triethylamine, pyridine) or a compound represented by the general formula (1)
It can be produced by reacting the carboxylic acid represented by 6) with a desired alcohol in the presence of triphenylphosphine and DEAD. The general formula (1)
The carboxylic acid represented by 6) is represented by the general formula (19)
The aromatic acetylene compound represented by the formula (4) and the general formula (2)
0) An ester derivative represented by (Chemical formula 14) (Z ₃ represents a protecting group such as a benzyl group, a methyl group, an ethyl group, etc.) under an inert gas atmosphere under a palladium catalyst [for example, dichlorobis (triphenylphosphine)]. Palladium, tetrakis (triphenylphosphine) palladium], copper iodide and a base (eg, triethylamine, pyridine) to produce an acetylene compound represented by the general formula (21). 21) (Formula 14)
By removing the protecting group of the acetylene compound represented by

[0088]

Embedded image

The carboxylic acid represented by the general formula (18) is the same as the carboxylic acid represented by the general formula (16), for example,
It can be produced by catalytic hydrogenation in the presence of a catalyst (eg, palladium / carbon, palladium / alumina) under a hydrogen atmosphere. Specific examples of the non-optically active ester compound used in the liquid crystal composition of the present invention include compounds as shown in Table 5 (Tables 33 to 51). In the table, the substitution position of X ₃ is the meta position with respect to Y ₃ .

[0090]

[Table 33]

[0091]

[Table 34]

[0092]

[Table 35]

[0093]

[Table 36]

[0094]

[Table 37]

[0095]

[Table 38]

[0096]

[Table 39]

[0097]

[Table 40]

[0098]

[Table 41]

[0099]

[Table 42]

[0100]

[Table 43]

[0101]

[Table 44]

[0102]

[Table 45]

[0103]

[Table 46]

[0104]

[Table 47]

[0105]

[Table 48]

[0106]

[Table 49]

[0107]

[Table 50]

[0108]

[Table 51] Specific examples of the case where R ₃ of the non-optically active ester compound represented by the general formula (2) is a group represented by the general formula (3) are shown in Table 6 (Tables 52 to 60). Such compounds can be mentioned. In the table, the substitution position of X ₃ is the meta position with respect to Y ₃ .

[0109]

[Table 52]

[0110]

[Table 53]

[0111]

[Table 54]

[0112]

[Table 55]

[0113]

[Table 56]

[0114]

[Table 57]

[0115]

[Table 58]

[0116]

[Table 59]

[0117]

[Table 60]

The liquid crystal composition of the present invention comprises at least one optically active naphthalene compound represented by the general formula (1):
It is a liquid crystal composition comprising at least one non-optically active ester compound represented by the general formula (2), and the content thereof is not particularly limited, but is preferably at least one type of the general formula (1) The content of the optically active naphthalene compound represented by the formula (1) is 50 to 97% by weight;
The content of the non-optically active ester compound represented by the general formula (2) is 3 to 50% by weight, more preferably at least one kind of the optically active naphthalene compound represented by the general formula (1). The content is 60 to 95% by weight, and the content of at least one non-optically active ester compound represented by the general formula (2) is 5 to 40% by weight. Further, the liquid crystal composition of the present invention further comprises at least one liquid crystal composition for the purpose of adjusting the temperature range of the liquid crystal phase or adjusting the physical properties of the liquid crystal composition.
A non-optically active naphthalene compound represented by the general formula (4) may be contained.

In the non-optically active naphthalene compound represented by the general formula (4) (Formula 15) used in the liquid crystal composition of the present invention, R ₄ and R ₅ each have 3 carbon atoms which may be substituted with a halogen atom. To 24 linear or branched alkyl groups, 3 to 24 carbon atoms which may be substituted with halogen atoms, linear or branched unsaturated alkyl groups, 3 carbon atoms which may be substituted with halogen atoms Represents an alkoxyalkyl group having from 24 to 24 or an unsaturated alkoxyalkyl group having from 3 to 24 carbon atoms which may be substituted with a halogen atom, and specific examples thereof include the groups exemplified as specific examples of the above-described R ₂ and the like. be able to.

[0120]

Embedded image In the non-optically active naphthalene compound represented by the general formula (4), Y ₄ represents a single bond or a —O— group, and Y ₅ represents —
A represents a COO— group or a —CH ₂ O— group, and A represents any group represented by the following formula (Formula 16). Represent.

[0121]

Embedded image When the non-optically active naphthalene compound represented by the general formula (4) is used in the liquid crystal composition of the present invention, only one kind of the non-optically active naphthalene compound represented by the general formula (4) may be used. , Or more than one. When a plurality of non-optically active naphthalene compounds represented by the general formula (4) are used in the liquid crystal composition of the present invention, R ₄ and / or R ₅ may be the same or different. The non-optically active naphthalene compound represented by the general formula (4) used in the liquid crystal composition of the present invention has the following structure (Formula 17) depending on the type of Y ₅ and A.

[0122]

Embedded image The method for producing the non-optically active naphthalene compound represented by the general formula (4) used in the liquid crystal composition of the present invention is the method described in the above-mentioned method for producing the optically active naphthalene compound represented by the general formula (1). It can be produced by a method using a non-optically active alcohol instead of an optically active alcohol by utilizing the same production method as described above.

When the compound represented by the general formula (4) is used in the liquid crystal composition of the present invention, the compound represented by the general formula (1)
The content of the non-optically active naphthalene compound represented by the general formula (4) in the mixture of the optically active naphthalene compound and the non-optically active ester compound represented by the general formula (4) is not particularly limited, but is preferably The content of the optically active naphthalene compound represented by the formula (1) and the non-optically active ester compound represented by the general formula (2) is 99 to 20.
% By weight, the content of the non-optically active naphthalene compound represented by the general formula (4) is 1 to 80% by weight, more preferably the optically active naphthalene compound represented by the general formula (1) The content of the non-optically active ester compound represented by the formula (2) is 99 to 25% by weight, and the general formula (4)
The content of the non-optically active ester compound represented by
5% by weight.

The optically active naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention includes a compound exhibiting liquid crystallinity by itself and a compound exhibiting no liquid crystallinity. Compounds exhibiting liquid crystallinity include compounds exhibiting chiral smectic C phase (hereinafter abbreviated as S _C ^* phase) and compounds exhibiting liquid crystallinity but exhibiting no S _C ^* phase. Each of these compounds can be effectively used as a component of the liquid crystal composition of the present invention. Also,
The non-optically active ester compound represented by the general formula (2) and the non-optically active naphthalene compound represented by the general formula (4) include a compound exhibiting liquid crystallinity by itself and a compound not exhibiting liquid crystallinity. is there. Compounds exhibiting liquid crystallinity include compounds exhibiting smectic C phase (hereinafter abbreviated as S _C phase) and compounds exhibiting liquid crystallinity but exhibiting no S _C phase. Each of these compounds can be effectively used as a component of the liquid crystal composition of the present invention.

In the case where the non-optically active naphthalene compound represented by the general formula (4) is not used in the liquid crystal composition of the present invention, the optically active naphthalene compound represented by the general formula (1) according to the present invention may be used. At least one of the non-optically active ester compounds represented by the formula (2) is preferably a compound exhibiting an S _C phase or an S _C ^* phase. When a non-optically active naphthalene compound represented by the general formula (4) is used in the liquid crystal composition of the present invention, the optically active naphthalene compound represented by the general formula (1) according to the present invention and the general formula (2) Of the non-optically active ester compound represented by the general formula (4) and the non-optically active naphthalene compound represented by the general formula (4), at least one compound is preferably a compound exhibiting an S _C phase or an S _C ^* phase.

Further, the liquid crystal composition of the present invention further comprises:
A desired compound can be added for the purpose of lowering the melting point, lowering the viscosity, improving the response speed, improving the tilt angle, or improving the memory stability. Here, as the compound that can be added as desired, for example, a nematic liquid crystal compound, a liquid crystalline aromatic compound, a non-liquid crystalline aromatic compound, a liquid crystalline aliphatic compound, and a Liquid crystalline aliphatic compounds can be exemplified. The amount of the compound added as desired is preferably 20% by weight or less, more preferably 10% by weight or less, based on the liquid crystal composition of the present invention.

The liquid crystal composition of the present invention causes a switching phenomenon when a voltage is applied, and can be applied to a liquid crystal display device having a short response time utilizing the switching phenomenon. The liquid crystal composition of the present invention has a response time, a memory stability, a layer structure in the S _{C *} phase, a tilt angle, an alignment characteristic on an alignment film, and a liquid crystal compound which are compared with conventionally known liquid crystal compositions. Excellent in compatibility between them.

Next, the liquid crystal device of the present invention will be described. The liquid crystal element of the present invention has the liquid crystal composition of the present invention disposed between a pair of electrode substrates. FIG. 1 is a schematic cross-sectional view showing an example of a liquid crystal element having a chiral smectic phase for explaining the configuration of a liquid crystal element utilizing ferroelectricity. In the liquid crystal element, a liquid crystal layer 1 exhibiting a chiral smectic phase is disposed between a pair of substrates 2 provided with a transparent electrode 3 and an insulating alignment control layer 4, respectively, and the thickness of the liquid crystal layer is set by a spacer 5. And a connection is made between a pair of transparent electrodes 3 via a lead wire 6 so that a voltage can be applied from a power supply 7. Further, the pair of substrates 2 is sandwiched by a pair of polarizing plates 8 arranged in a crossed Nicols state, and a light source 9 is arranged outside one of them. Examples of the material of the substrate 2 include glass such as soda lime glass and borosilicate glass and polycarbonate, polyether sulfone,
Transparent polymers such as polyacrylates are exemplified. The transparent electrodes 3 provided on the two substrates 2 include, for example, I
n ₂ O ₃ , SnO ₂ or ITO (indium tin
A transparent electrode formed of a thin film of oxide (Indium Tin Oxide) may be used.

The insulating alignment control layer 4 is for rubbing a thin film of a polymer such as polyimide with a flocked cloth such as nylon, acetate, rayon or the like to align the liquid crystal. Examples of the material of the insulating orientation control layer 4 include silicon nitride, silicon nitride containing hydrogen, silicon carbide, silicon carbide containing hydrogen, silicon oxide, boron nitride, and boron nitride containing hydrogen. , Cerium oxide, aluminum oxide, zirconium oxide, inorganic substance insulating layer such as titanium oxide and magnesium fluoride, polyvinyl alcohol, polyimide, polyamide imide, polyester imide, polyether imide,
Organic materials such as polyether ketone, polyether ether ketone, polyether sulfone, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin, urea resin, acrylic resin, etc. An insulating orientation control layer having a two-layer structure in which an organic insulating layer is formed on an inorganic insulating layer, or an insulating orientation control layer consisting only of an inorganic insulating layer or an organic insulating layer. You may. When the insulating orientation control layer is an inorganic insulating layer, it can be formed by an evaporation method or the like. In the case of an organic insulating layer, an organic insulating layer material or a solution of a precursor thereof is spinner-coated, penetrated-coated, screen-printed, spray-coated,
It can be formed by coating by a roll coating method or the like, removing the solvent under predetermined conditions (for example, under heating), and baking if desired.

In forming the organic insulating layer, if necessary, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropylmethyldiethoxy Silane, γ-glycidyloxypropyltriethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, N-β- (aminoethyl) -γ-amino Propylmethyldimethoxysilane, N-β- (aminoethyl) -γ-aminopropyltrimethoxysilane, N
-Β- (aminoethyl) -γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane,
Surface treatment may be performed using a silane coupling agent such as γ-aminopropyltriethoxysilane or the like, and then an organic insulating layer material or a precursor thereof may be applied. The thickness of the insulating orientation control layer 4 is usually 10 Å to 1 μm, preferably 10 to 3000 Å, and more preferably 10 to 1000 Å.

The two substrates 2 are kept at an arbitrary interval by the spacer 5. For example, silica beads or alumina beads having a predetermined diameter are sandwiched between the substrates 2 as spacers, and the periphery of the two substrates 2 is sealed with a sealant (for example, an epoxy-based adhesive) so as to be at an arbitrary interval. Can be kept. Further, a polymer film or glass fiber may be used as the spacer. A liquid crystal exhibiting a chiral smectic phase is sealed between the two substrates. The thickness of the liquid crystal layer 1 is generally set to 0.5 to 20 μm, preferably 1 to 5 μm, and more preferably 1 to 3 μm. The transparent electrode 3 is connected to an external power supply 7 by a lead wire. Outside the substrate 2, a pair of polarizing plates 8 whose polarization axes are in, for example, a crossed Nicols state are arranged. The example shown in FIG. 1 is of a transmission type and includes a light source 9. Further, the liquid crystal device using the liquid crystal composition of the present invention can be applied not only as a transmissive device shown in FIG. 1 but also as a reflective device.

The display system of the liquid crystal device using the liquid crystal composition of the present invention is not particularly limited, but
For example, (a) helical distortion type, (b) SSFLC (surface stabilized ferroelectric liquid crystal) type, (c) TSM (transient scattering mode) type, (d) GH ( A guest-host type display scheme can be used.
In addition, the non-optically active ester compound of the present invention and a liquid crystal composition containing the compound may be used in a field other than a liquid crystal element for display (for example, an electronic material such as a nonlinear optical function element, a capacitor material, a limiter, a memory, an amplifier). , Modulators and other electronic elements,
It can be applied to heat, light, pressure, mechanical deformation, and voltage conversion elements, sensors, and power generation elements such as thermoelectric power generation elements.

[0133]

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples. The symbols I, S _A and S _C ^* in each example and table have the following meanings. I: Isotropic liquid S _A : Smectic A phase S _C ^* : Chiral smectic C phase The measurement in each example was performed according to the following method. -Phase transition temperature: Measured using a polarizing microscope equipped with a temperature controller. Optical response time: ± 20 V, 10 Hz rectangular wave is applied to the liquid crystal cell, the response of the liquid crystal cell under a polarizing microscope is detected using a photomultiplier tube, and the response time (transmission light amount: 10% − 90%). Tilt angle: ± 20 V, 1 Hz rectangular wave was applied to the liquid crystal cell, and the angle (2θ) of the extinction position at two points was visually determined under a polarizing microscope, and calculated (2θ / 2). Spontaneous polarization: A triangular wave of ± 20 V, 120 Hz was applied to the liquid crystal cell, and the spontaneous polarization was determined by a triangular wave method. That is, the current accompanying the polarization reversal was converted into a voltage change by a current-voltage converter, and the integrated value of the polarization reversal current was obtained from a digital oscilloscope.・ Memory stability: 200 μs, ± 20 V,
It was determined from the retention of the amount of transmitted light when a bipolar pulse with a duty ratio of 1: 200 (FIG. 2) was applied. The larger this value is, the higher the memory stability is. ΔT: ± 20 V for liquid crystal cell, duty ratio 1: 200
Was applied, and the pulse width was determined from the pulse width when the memory stability reached 80%. The smaller the value is, the shorter the pulse can be driven. Contrast ratio: ± 20 V, 10 Hz rectangular wave is applied to the liquid crystal cell, the response of the liquid crystal cell under a polarizing microscope is detected using a photomultiplier tube, and the output difference between the bright and dark photomultiplier tubes ( mv). The larger this value is, the higher the contrast ratio is.

Example 1 Preparation of Liquid Crystal Composition The following compound (Chemical Formula 18) was mixed in the following ratio, melted at 100 ° C., and then cooled to room temperature.
A liquid crystal composition (ferroelectric liquid crystal composition) was prepared. The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0135]

Embedded image

Example 2 Preparation of Liquid Crystal Element Two glass plates having a thickness of 1.1 mm were prepared, an ITO film was formed on each of the glass plates, and a surface treatment was further performed. CRD-8616 (polyamide manufactured by Sumitomo Bakelite Co., Ltd.) was spin-coated on the glass plate with the ITO film as an insulating orientation control layer so as to have a thickness of 200 Å, and then baked at 90 ° C. for 1 hour. The firing was performed at 200 ° C. for 1 hour. After cooling the glass plate to room temperature, this orientation control layer is subjected to a rubbing treatment, and thereafter, silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates, and the rubbing treatment shafts of the two glass plates are separated. Were bonded to each other using a sealing agent so that the cells were antiparallel to each other, thereby forming a cell. Thereafter, the cell was heated to 120 ° C., the liquid crystal composition prepared in Example 1 heated to 120 was injected, and cooled to room temperature at a rate of 2 ° C./min. When this liquid crystal cell was placed in a crossed Nicol state polarizing microscope and its alignment state was observed, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, room temperature (25
(° C.) and the physical properties of the liquid crystal composition were measured.
It was noted in.

Example 3 Preparation of Liquid Crystal Element Two glass plates having a thickness of 1.1 mm were prepared, an ITO film was formed on each of the glass plates, and a surface treatment was further performed. This glass plate with an ITO film is spin-coated with polyvinyl alcohol as an insulating orientation control layer so that the film thickness becomes 200 Å, and then 120 ° C.
After baking for 30 minutes and cooling the glass plate to room temperature, a rubbing treatment is performed on this orientation control layer, and then silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates.
The two glass plates were stuck together using a sealant such that the respective rubbing axes of the two glass plates were antiparallel to each other, thereby forming a cell. Then, this cell is
The liquid crystal composition prepared in Example 1 was heated to 0 ° C.
, And cooled to room temperature at a rate of 2 ° C./min. When this liquid crystal cell was placed in a crossed Nicol state polarizing microscope and its alignment state was observed, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 4 Preparation of Liquid Crystal Composition The following compound (Chemical Formula 19) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0139]

Embedded image

Example 5: Preparation of a liquid crystal device Example 3 was repeated except that the liquid crystal composition prepared in Example 4 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 6: Preparation of liquid crystal composition The following compound (Chemical Formula 20) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0142]

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Example 7: Preparation of a liquid crystal element Example 3 was repeated except that the liquid crystal composition prepared in Example 6 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 8: Preparation of liquid crystal composition The following compound (Chemical Formula 21) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0145]

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Example 9: Preparation of liquid crystal device Example 3 was repeated except that the liquid crystal composition prepared in Example 8 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 10: Preparation of liquid crystal composition The following compound (formula 22) was mixed in the ratio shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0148]

Embedded image

Example 11: Preparation of liquid crystal element Example 3 was repeated except that the liquid crystal composition prepared in Example 10 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 12: Preparation of liquid crystal composition The following compound (Formula 23) was mixed at the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0151]

Embedded image

Example 13: Preparation of a liquid crystal element Example 3 was repeated except that the liquid crystal composition prepared in Example 12 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 14: Preparation of liquid crystal composition The following compound (Formula 24) was mixed in the ratio shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0154]

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Example 15: Preparation of a liquid crystal device Example 3 was repeated except that the liquid crystal composition prepared in Example 14 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 16: Preparation of liquid crystal composition The following compound (Chemical Formula 25) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0157]

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Example 17: Preparation of a liquid crystal element The procedure of Example 3 was repeated, except that the liquid crystal composition prepared in Example 16 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 18: Preparation of liquid crystal composition The following compound (Chemical Formula 26) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0160]

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Example 19: Preparation of a liquid crystal element In Example 3, instead of using the liquid crystal composition prepared in Example 1, the liquid crystal composition prepared in Example 18 was used. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 20: Preparation of liquid crystal composition The following compound (Chemical Formula 27) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0163]

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Example 21: Preparation of a liquid crystal element Example 3 was repeated except that the liquid crystal composition prepared in Example 20 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Example 22: Preparation of liquid crystal composition The following compound (Chemical Formula 28) was mixed in the following ratio,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0166]

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Example 23: Preparation of liquid crystal device Example 3 was repeated except that the liquid crystal composition prepared in Example 22 was used instead of the liquid crystal composition prepared in Example 1. A liquid crystal element was manufactured according to the operation described. From observation of the alignment state with a polarizing microscope in a crossed Nicols state, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 7.

Comparative Example For comparison, a liquid crystal composition containing no non-optically active ester compound of the present invention was prepared, and a liquid crystal device was produced. That is, the following compound group (Chemical Formula 29) was mixed and used in the ratio shown below, and heated and melted at 100 ° C. to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below.

[0169]

Embedded image Next, two glass plates having a thickness of 1.1 mm were prepared, an ITO film was formed on each of the glass plates, and a surface treatment was further performed. The glass plate with the ITO film was spin-coated with an insulating orientation control layer (polyvinyl alcohol), baked at 120 ° C. for 30 minutes after film formation. The alignment film was subjected to a rubbing treatment, and silica beads having an average particle size of 1.9 μm were sprayed on one glass plate. Thereafter, a glass plate was bonded using a sealant so that the respective rubbing treatment axes were antiparallel to each other, thereby producing a cell. This cell is 12
The liquid crystal composition was heated to 0 ° C., and the heated liquid crystal composition (120 ° C.) was injected, and then cooled at a rate of 3 ° C./min to produce a liquid crystal element. When this liquid crystal element was sandwiched between two polarizing plates arranged in a crossed Nicols state and a rectangular wave of ± 20 V and 10 Hz was applied, a clear switching phenomenon was observed. In addition, a good uniform alignment state was observed with a polarizing microscope, and no alignment defects such as zigzag defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were evaluated and are summarized in Table 7.

[0170]

[Table 61] As is clear from Table 7, the liquid crystal composition of the present invention has a relatively short response time, a stable memory state, a short ΔT, and a high contrast ratio. I understand.

[0171]

According to the present invention, orientation, memory stability,
It has become possible to provide a liquid crystal composition having excellent response time, contrast ratio, and the like.

[Brief description of the drawings]

FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element using a liquid crystal exhibiting a chiral smectic phase.

FIG. 2 is a graph showing a relationship between voltage and time of a bipolar pulse for measuring memory stability.

[Explanation of symbols]

1: Liquid crystal layer having a chiral smectic phase 2: Substrate 3: Transparent electrode 4: Insulating alignment control layer 5: Spacer 6: Lead wire 7: Power supply 8: Polarizing plate 9: Light source _IO : Incident light I: Transmitted light

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Masakatsu Nakatsuka 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Mitsui Chemicals, Inc.

Claims (6)

[Claims] 1. An optically active naphthalene compound represented by at least one kind of the following general formula (1) and a non-optically active compound represented by at least one kind of the following general formula (2): A liquid crystal composition containing an ester compound. Embedded image [Wherein, R ₁ represents a linear or branched alkyl group having 3 to 24 carbon atoms, R ^* has an optically active asymmetric carbon, and may be a carbon atom which may be substituted by a halogen atom or an alkoxy group. Represents an alkyl group of Formulas 3 to 24, Y ₁ represents a single bond or a —O— group, and Y ₂ represents a —COO— group or —C
Represents an H ₂ O— group, X ₁ and X ₂ represent a halogen atom or a hydrogen atom, and n ₁ represents 0 or 1.] [Wherein, R ₂ and R ₃ each represent a linear or branched alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or 3 to 24 carbon atoms which may be substituted with a halogen atom. A linear or branched unsaturated alkyl group of
A straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or
Represents a linear or branched unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, and R ₃ is a cycloalkyl group represented by the following general formula (3) Alkyl group (Wherein, p represents an integer of 0 to 4, and q represents an integer of 2 to 8), and Y ₃ is a single bond, a —O— group,
OO— or —OCOO—, and X ₃ represents a hydrogen atom or a halogen atom. 2. The liquid crystal composition according to claim 1, wherein at least one of the optically active naphthalene compounds represented by the general formula (1) is a compound having an asymmetric carbon at a bond of R ^* . 3. The liquid crystal composition according to claim 1, comprising at least two optically active naphthalene compounds represented by the general formula (1). 4. The content of the optically active naphthalene compound represented by the general formula (1) is 50 to 97% by weight, and the content of the non-optically active ester compound represented by the general formula (2) is 3 to 3% by weight. The liquid crystal composition according to any one of claims 1 to 3, which is 50% by weight. 5. The liquid crystal composition according to claim 1, further comprising at least one non-optically active naphthalene compound represented by the following general formula (4). Embedded image [Wherein, R ₄ and R ₅ each represent a linear or branched alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or 3 to 24 carbon atoms which may be substituted with a halogen atom. A linear or branched unsaturated alkyl group of
A straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or
A linear or branched unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, Y ₄ represents a single bond or —O— group, and Y ₅ represents —CO
Represents an O— group or a —CH ₂ O— group, and A is any group represented by the following formula (Formula 5) (Wherein, X _{4 to} X ₆ each represent a halogen atom or a hydrogen atom) 6. A liquid crystal device comprising the liquid crystal composition according to claim 1 interposed between a pair of electrode substrates.