JP2001220368A - Optically inactive ester compound, liquid crystal composition and liquid crystal element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal compound maintaining a bookshelf structure, having a slight reduction in a tilt angle and low viscosity. SOLUTION: This optically inactive ester compound is represented by general formula (1) [R1 and R2 are each an alkyl group, an alkenyl group, an alkoxyalkyl group or an alkenyloxyalkyl group; Y1 is COO group or OCOO group; Y2 is a single bond or an O group; Z is c≡C or an CH2CH2 group].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel non-optically active ester compound. More specifically, the present invention relates to a novel non-optically active ester compound useful as a component of a liquid crystal composition used for a liquid crystal display device, a liquid crystal composition containing the compound, and a liquid crystal device using the liquid crystal composition.

[0002]

2. Description of the Related Art Liquid crystal display devices have been used as various displays because of their thinness and light weight and low power consumption. 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 (super twisted nematic) type display elements having a twist angle of 180 to 270 ° have been developed, but the response time is still inferior. 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 ferroelectric liquid crystal, which has been actively studied in recent years, there is a possibility that the response time can be significantly improved [N.
A. Clark et al .; Applied Phys. Lett., 36 , 899 (1980)].

This method uses 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 phases are ferroelectric liquid crystal phases exhibiting ferroelectricity. These smectic liquid crystal phases belong to a tilt-type chiral smectic phase, but practically, use of a chiral smectic C phase, which has low viscosity and is expected to have high-speed response, is being studied. . In recent years, a display system using a chiral smectic CA phase (antiferroelectric phase), which is a higher order phase of the chiral smectic C phase, has been actively studied in recent years [L.
Chandani et al .; Jpn. J. App. Phys., 27 , L719 (1988).
].

Various liquid crystal compounds exhibiting the tilt-type smectic phase have been studied so far, and a large number of compounds have already been searched for and manufactured. However,
Numerous characteristics (high-speed response, alignment, high contrast ratio, threshold characteristics, memory stability, 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 to optimize the liquid crystal composition, and a ferroelectric liquid crystal composition obtained by mixing several liquid crystal compounds is used.

The tilt-type chiral smectic composition includes not only a liquid crystal composition consisting of a compound exhibiting a tilt-type chiral smectic liquid crystal phase but also a compound or a composition exhibiting a non-chiral tilt-type smectic phase. As a mixture, one or more compounds exhibiting a tilt-type chiral smectic phase can be mixed to obtain a whole as a tilt-type chiral smectic liquid crystal composition. Furthermore, a compound or composition exhibiting a tilt-based smectic phase is used as a basic substance, and is optically active but does not exhibit a tilt-based chiral smectic liquid crystal phase.
There have been reports that a kind or a plurality of compounds are mixed to form a tilt-type chiral smectic liquid crystal composition as a whole [Mol. Cryst. Liq. Cryst., 89 , 327 (1982)].

In summary, one or more compounds that are optically active irrespective of whether they exhibit a tilt-type chiral smectic liquid crystal phase and a compound that exhibits an achiral, tilt-type smectic liquid crystal phase are mixed. It can be seen from the result that a tilt-based smectic liquid crystal composition can be formed. As described above, various compounds can be used as components of the liquid crystal composition, but in practice, a liquid crystal compound or a liquid crystal compound exhibiting a tilt-based smectic phase or a chiral smectic phase in a wide temperature range including room temperature. Mixtures are desirable. As the components of these 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, liquid crystal compositions containing these compounds as constituents also have a layer structure in a smectic phase (ideally a bookshelf structure),
It cannot be said that it has sufficient properties such as viscosity, its temperature dependency, and threshold properties. There is a report of adding a compound represented by the general formula (3) or (4) to a smectic liquid crystal composition to lower the viscosity of the smectic liquid crystal composition (JP-A-6-122875).

[0007]

Embedded image Wherein R and R ′ represent an alkyl group or an alkoxy group; R ^* represents an alkyl group having an asymmetric carbon;
And B represent a hydrogen atom or a fluorine atom, and Y represents a methylene chain.

However, when the compound is used,
There is a problem that the tilt angle of the liquid crystal composition is reduced. Therefore, a material that reduces the viscosity of the liquid crystal material without reducing the tilt angle is desired. It is also known that a tilt-based smectic liquid crystal material undergoes volume shrinkage when transitioning from a non-tilt-based liquid crystal phase to a tilt-based liquid crystal phase, resulting in a chevron structure. Such a tilt-based smectic material having a chevron structure has a problem that the tilt angle (θ) and the memory angle (θm) are not equal due to the layer structure, and thus “leakage” of light transmittance occurs during actual driving. (Preprints of the lecture meeting of the Japanese Liquid Crystal Society, 1999, p. 418, 2D12). For this reason, a liquid crystal composition having a bookshelf structure in which θ-θm is reduced is desired. Thus, at present, as a smectic liquid crystal material, a high tilt angle, a low viscosity (high-speed response, a low threshold voltage), and a bookshelf structure (low θ) are used.
-Θm) is desired.

[0009]

SUMMARY OF THE INVENTION An object of the present invention is to provide a smectic liquid crystal device with various characteristics such as a layer structure, orientation, a threshold value, and a contrast ratio when the compound is mixed with a smectic liquid crystal composition. And a liquid crystal composition containing the compound, and a liquid crystal device using the composition.

[0010]

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 non-optically active ester compound, and have reached the present invention. That is, the present invention relates to a non-optically active ester compound represented by the general formula (1) (Formula 4). Further, the present invention relates to a liquid crystal composition containing at least one non-optically active ester compound represented by the general formula (1), and a liquid crystal device using the composition.

[0011]

Embedded image [Wherein, R ₁ and R ₂ each independently represent a linear or branched alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or 3 carbon atoms which may be substituted with a halogen atom. To 24 linear or branched alkenyl groups, 3 to 2 carbon atoms which may be substituted with a halogen atom
4 straight-chain or branched-chain alkoxyalkyl group, or 3 to 2 carbon atoms which may be substituted with a halogen atom.
4 represents a linear or branched alkenyloxyalkyl group, Y ₁ represents a —COO— group or —OCOO— group, Y ₂ represents a single bond or —O— group, and Z represents —C≡C.
— Or —CH ₂ CH ₂ —.

[0012]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. In the non-optically active ester compound represented by the general formula (1) of the present invention, Z is a —C≡C— group or —CH ₂ CH ₂ —.
When the group, Y ₁ is a —COO— group or —OCOO— group, and Y ₂ is a single bond or an —O— group, the following (1-A1) to (1-A4) and (1-B1) ) To (1)
-B4) has eight types of structures (Formula 5). Preferred structures are (1-A1) to (1-A4), (1-B2) and (1
-B4), and a more preferred structure is (1-A2),
(1-A4) and (1-B2).

[0013]

Embedded image

In the non-optically active ester compound represented by the general formula (1) of the present invention, R ₁ and R ₂ each independently represent a C 3 carbon atom which may be substituted with a halogen atom.
To 24 straight-chain or branched-chain alkyl groups, C3-C24 straight-chain or branched-chain alkenyl groups which may be substituted with halogen atoms, and C3-C24 which may be substituted with halogen atoms. Represents a straight-chain or branched-chain alkoxyalkyl group, or an alkenyloxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom. R ₁ and R ₂ preferably have 4 to 18 carbon atoms.
And more preferably 5 to 16. R ₁ and R ₂ preferably have 3 to ₂ carbon atoms containing no asymmetric carbon.
4 straight-chain or branched-chain alkyl groups, straight-chain or branched-chain alkenyl groups having 3 to 24 carbon atoms and containing no asymmetric carbon,
Represents a straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon, or an alkenyloxyalkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon; A straight-chain or branched-chain alkyl group having from 24 to 24 carbon atoms or a straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms which does not contain an asymmetric carbon atom.

Specific examples of the groups represented by R ₁ and R ₂ include, for example, n-propyl group, n-butyl group, n-pentyl group, 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 A 1-n-butylbutyl group, a 1-methylpentyl group, a 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-pentyl Heptyl 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 group, 3-methylbutyl group, 3-methylpentyl group, 3-ethylpentyl group, 4-methylpentyl group, 4-ethylhexyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 2, 4,4-trimethylpentyl group, 2,3,3,4-tetramethylpentyl group, 3-methylhexyl group, 2,5-dimethylhexyl group, 3-ethylhexyl group, 3,5,5, -trimethylhexyl group An alkyl group such as a 4-methylhexyl group, a 6-methylheptyl group, a 3,7-dimethyloctyl group, a 6-methyloctyl group,

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, 3-chloro-n-
Propyl group, 2-chloro-n-butyl group, 4-chloro-
n-butyl group, 2-chloro-n-pentyl group, 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-perfluoro Octyl 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-
an n-perfluorohexadecyl group,

1,1,3-trihydro-n-perfluoropropyl group, 1,1,3-trihydro-n-perfluorobutyl group, 1,1,4-trihydro-n-perfluorobutyl group, 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-perfluoro Decyl) propyl group, 3- (n-perfluorododecyl) propyl group, 4- (perfluoroethyl) butyl group, 4- (n-
Perfluoropropyl) butyl, 4- (n-perfluorobutyl) butyl, 4- (n-perfluoropentyl) butyl, 4- (n-perfluorohexyl) butyl, 4- (n-perfluoro Heptyl) butyl group, 4
-(N-perfluorooctyl) 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- (perfluoroethyl) heptyl group, 7- (n An alkyl group substituted with a halogen atom such as -perfluoropropyl) heptyl group, 7- (n-perfluorobutyl) heptyl group, 7- (n-perfluoropentyl) heptyl 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-heptyloxydecyl group, octyloxymethyl group, 2-n
-Octyloxyethyl group, 3-n-octyloxypropyl group, 4-n-octyloxybutyl group, 5-n-
Octyloxypentyl group, 6-n-octyloxyhexyl 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-undecyloxy Butyl group, 6-n-undecyloxyhexyl group, 8-n-undecyloxyoctyl 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 group, 2-2-ethoxypropyl group, 2- n-propyloxypropyl group, 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, 1
0-isopropyloxydecyl group, isobutyloxymethyl group, 2-isobutyloxyethyl group, 3-isobutyloxypropyl group, 4-isobutyloxybutyl group,
5-isobutyloxypentyl group, 6-isobutyloxyhexyl 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 group,

A 4- (2'-methoxyethoxy) butyl group, a 4- (2'-ethoxyethoxy) butyl group,
(2′-isopropyloxyethoxy) butyl group, 4-
(2′-isobutyloxyethoxy) butyl group, 4-
(2′-n-butyloxyethoxy) butyl group, 4-
(2′-n-hexyloxyethoxy) butyl group, 4-
(3'-n-propyloxypropyloxy) 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 group, (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'
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)
A hexyl group, an alkoxyalkyl group such as a 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- (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,

1,1-dihydro-perfluoro (2-methoxyethyl) group, 1,1-dihydro-perfluoro (3-n-propyloxypropyl) group, 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-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 group, 4-heptenyl group, 5-heptenyl group, 6-heptenyl group, 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, 3 Alkenyl groups such as 7,7-dimethyl-6-octenyl 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-perfluorooctyl-2-propenyl group, etc. An alkenyl group substituted with a halogen atom,

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′-
Alkenyloxyalkyl groups such as propenyloxy) decyl group, 2- (2′-propenyloxy) -perfluoroethyl group, 3- (2′-propenyloxy) -perfluoropropyl group, 4- (2′-propenyloxy )-
A perfluorobutyl group, a 5- (2′-propenyloxy) -perfluoropentyl group, a 6- (2′-propenyloxy) -perfluorohexyl group, a 7- (2′-propenyloxy) -perfluoroheptyl group, 8-
An alkenyloxyalkyl group substituted by a halogen atom such as (2′-propenyloxy) -perfluorooctyl group can be mentioned.

In the non-optically active ester compound of the present invention represented by the general formula (1), Y ₁ represents a —COO— group or a —OCOO— group, preferably a —COO— group. Y ₂ represents a single bond or an —O— group, and preferably represents an —O— group. Specific examples of the non-optically active ester compound represented by the general formula (1) of the present invention include compounds as shown in Table 1 (Tables 1 to 3) and Table 2 (Table 4) below. be able to.

[0038]

[Table 1]

[0039]

[Table 2]

[0040]

[Table 3]

[0041]

[Table 4] The non-optically active ester compound represented by the general formula (1) of the present invention can be produced, for example, through the following steps. A process for producing a non-optically active ester compound represented by the general formula (1) wherein Z is a —C≡C— group (Formula 6):

[0042]

Embedded image

A-: When Y ₂ is an —O— group: a compound represented by the general formula (5) (X represents a bromine atom, an iodine atom or a trifluoromethanesulfonate group) and a base (for example, carbonic acid) In the presence of potassium, sodium carbonate, potassium hydroxide, sodium hydroxide, an alkylating agent (LR ₂ : L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom or a p-toluenesulfonate group) ) To give a compound represented by the general formula (6A). A-: When Y ₂ is a single bond: An alkylacetylene compound (R ₃ -C≡C
H: R ₃ represents a group having two carbon atoms less than R ₂ ) using an inert gas atmosphere in the presence of a palladium catalyst [eg, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium] and a base. To produce a compound represented by the general formula (8), and then reacting the compound in the presence of a catalyst such as platinum oxide.
By hydrogenation, a compound represented by the general formula (6B) is obtained.

B: Next, general formula (6) [general formula (6
A) or the compound represented by (6B)] and 3-methyl-
1-butyn-3-ol is reacted under an inert gas atmosphere in the presence of a palladium catalyst [for example, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium] and a base, to obtain a compound represented by the general formula ( The compound represented by 9) is treated with sodium hydroxide or potassium hydroxide to produce an acetylene compound represented by the general formula (10). C: Next, a compound represented by the general formula (11) (X represents a bromine atom, an iodine atom or a trifluoromethanesulfonate group) and an acetylene compound represented by the general formula (10) are converted into a palladium catalyst and a base. By reacting in an inert gas atmosphere in the presence of a compound (1), a non-optically active ester compound (1A) in which Z in the general formula (1) is a —C≡C— group can be produced. Alternatively,
The following step (Chem. 7) may be performed.

[0045]

Embedded image

That is, in the step C, the compound represented by the general formula (11 ′) is substituted for the compound represented by the general formula (11).
(Wherein Pr represents a protecting group such as a tetrahydropyranyl group) using the compound represented by the formula (12) to obtain a compound represented by the formula (12), and then represented by the formula (12) By removing the protecting group of the compound, a compound represented by the general formula (13) is produced and reacted with a carboxylic acid, or an alkyl chloroformate and a base (for example, triethylamine,
By reacting in the presence of pyridine), the compound represented by the general formula (1)
The non-optically active ester compound represented by A) can be produced. In the reaction of the compound represented by the general formula (13) with a carboxylic acid, a. After derivatizing the carboxylic acid to the acid chloride with a chlorinating agent such as thionyl chloride, oxalyl chloride, etc.
A method of reacting with a compound represented by the general formula (13) in the presence of a base (eg, triethylamine, pyridine), b. A carboxylic acid and a compound represented by the general formula (13) are converted to N, N′-dicyclohexylcarbodiimide (hereinafter referred to as D
A method of performing dehydration condensation in the presence of a catalyst (for example, N, N-dimethylaminopyridine) and a catalyst (for example, N, N-dimethylaminopyridine) can be used. Further, when Y ₂ is an —O— group, a non-optically active ester compound represented by the general formula (1A) can be produced according to the following step (Chem. 8).

[0047]

Embedded image

That is, dihydropyran (DHP) is reacted with the general formula (5) to protect a hydroxyl group as a tetrahydropyranyl group (—O-THP) to produce a compound represented by the general formula (14). Then, an acetylene compound represented by the general formula (16) is obtained by the same operation as in the step B. Next, the compounds represented by the general formulas (16) and (11) are reacted under an inert gas atmosphere in the presence of a palladium catalyst and a base to produce a compound represented by the general formula (17). Then, the protecting group is removed, and an alkylating agent (LR ₂ : L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom or a p-toluenesulfonate group) is added to a base (for example, sodium carbonate, The compound represented by the general formula (1A) can be produced by acting in the presence of potassium carbonate, sodium hydroxide, and potassium hydroxide). A process for producing a non-optically active ester compound represented by the general formula (1) wherein Z is a -CH ₂ CH ₂ -group (Formula 9)-

[0049]

Embedded image

A compound represented by the general formula (1A) is converted to a palladium catalyst (for example, palladium / carbon, palladium /
The presence of alumina), under a hydrogen atmosphere, by catalytic hydrogenation, in the general formula (1) Z is -CH ₂ CH
_The non-optically active ester compound (1B) which is a ₂ -group can be produced. The non-optically active ester compound of the present invention includes a compound showing liquid crystallinity by itself and a compound not showing liquid crystallinity. In addition, compounds that exhibit liquid crystallinity include:
There are compounds showing a smectic C phase (hereinafter abbreviated as S _C phase) and compounds showing liquid crystallinity but not showing an S _C phase. Each of these compounds can be effectively used as a component of a liquid crystal composition.

Next, the liquid crystal composition of the present invention will be described. The liquid crystal composition generally comprises two or more components,
The liquid crystal composition of the present invention contains at least one non-optically active ester compound of the present invention as an essential component. The liquid crystal composition of the present invention preferably includes a liquid crystal composition exhibiting a phase such as chiral smectic C, C _A , F, G, H, or I, and more preferably an S _C ^* phase or a chiral smectic C. _A liquid crystal composition exhibiting an _A ^* phase. The liquid crystal composition of the present invention is a non-optically active ester compound of the present invention, a liquid crystal compound having a chiral smectic phase, a compound selected from a liquid crystal compound having a smectic phase other than the non-optically active ester compound of the present invention and a compound selected from optically active compounds. A composition prepared by combining a plurality of the non-optically active ester compounds of the present invention.

The liquid crystal compound exhibiting a chiral smectic phase is not particularly limited. Examples thereof include an optically active phenylbenzoate liquid crystal compound, an optically active biphenylbenzoate liquid crystal compound, an optically active naphthalene liquid crystal compound, and an optically active phenyl liquid crystal compound. Examples include a naphthalene-based liquid crystal compound, an optically active tolan-based liquid crystal compound, an optically active phenylpyrimidine-based liquid crystal compound, an optically active naphthylpyrimidine-based liquid crystal compound, and an optically active tetralin-based liquid crystal compound.

The liquid crystal compound exhibiting a smectic phase other than the non-optically active ester compound of the present invention is not particularly limited. For example, a non-optically active phenylbenzoate liquid crystal compound, a non-optically active biphenylbenzoate liquid crystal compound , Non-optically active naphthalene liquid crystal compound, non-optically active phenylnaphthalene liquid crystal compound, non-optically active trans liquid crystal compound, non-optically active phenylpyrimidine liquid crystal compound, non-optically active naphthylpyrimidine liquid crystal compound, non-optically active tetralin liquid crystal Compounds can be mentioned. Specific examples of these compounds exhibiting a chiral smectic phase or a smectic phase include, for example, compounds represented by the general formula (2) (Formula 10). The compound is described, for example, in JP-A-62-10
No. 045 or JP-A-63-32748.

[0054]

Embedded image [Wherein, R ₁₁ and R ₁₂ are each independently a linear or branched alkyl group having 3 to 24 carbon atoms, which may have an optically active asymmetric carbon, or a linear chain having 3 to 24 carbon atoms. Or a branched-chain alkenyl group or a straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms, wherein Y ₁₁ and Y ₁₂ are a single bond, a —COO— group or a bonding group selected from a —O— group Represents

The optically active compound refers to a compound which does not exhibit liquid crystallinity by itself, but has a capability of exhibiting a chiral smectic phase by being mixed with a liquid crystal compound exhibiting a smectic phase or a liquid crystal composition exhibiting a smectic phase. Examples of the optically active compound include, but are not limited to, optically active phenylbenzoate-based non-liquid crystal compounds, optically active biphenylbenzoate-based non-liquid crystal compounds, optically active naphthalene-based non-liquid crystal compounds, and optically active phenylnaphthalene-based compounds. Non-liquid crystal compounds, optically active tolan non-liquid crystal compounds, optically active phenylpyrimidine non-liquid crystal compounds, optically active naphthylpyrimidine non-liquid crystal compounds, and optically active tetralin non-liquid crystal compounds can be exemplified.

The liquid crystal composition of the present invention may further comprise, as an optional component, a nematic liquid crystal compound in addition to the above essential components.
Even if it contains a compound having no liquid crystallinity other than the non-optically active ester compound of the present invention (for example, a dichroic dye such as an anthraquinone dye or an azo dye, and a conductivity-imparting agent or a life improving agent). Good. In the liquid crystal composition of the present invention,
Although the content of the non-optically active ester compound of the present invention is not particularly limited, it is usually 5 to 99% by weight,
Preferably, it is 10 to 90% by weight. Further, the non-optically active ester compound of the present invention can be mixed with the above-mentioned components for a liquid crystal composition at a desired mixing ratio, and has high compatibility.

The liquid crystal composition containing at least one non-optically active ester compound of the present invention has a tilt angle (contrast), a threshold characteristic, a response time, and a layer structure in a smectic phase, as compared with a conventional liquid crystal composition. It is excellent in liquid crystal temperature range, alignment characteristics on an alignment film, and compatibility as a liquid crystal material.

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. The power supply 7 is connected between the pair of transparent electrodes 3 via a lead wire 6 so that a voltage can be applied. 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 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 composed of only 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 applied by a spinner coating method, a penetration coating method, a screen printing method, a spray coating method, a roll coating method, or the like,
The solvent can be removed under a predetermined condition (for example, under heating) and, if desired, calcination can be performed. When forming the organic insulating layer, if necessary, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-
Glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropylmethyldiethoxysilane, γ-
Glycidyloxypropyltriethoxysilane, γ-methacryloxypropylmethyldimethoxysilane, γ-
Methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, N-β-
(Aminoethyl) -γ-aminopropylmethyldimethoxysilane, N-β- (aminoethyl) -γ-aminopropyltrimethoxysilane, N-β- (aminoethyl)-
Surface treatment is performed using a silane coupling agent such as γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, and 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 angstrom to 1 μm, preferably 1
0-3000 angstroms, more preferably 1
0 to 1000 angstroms.

The two substrates 2 are kept at an arbitrary interval by the spacer 5. For example, silica beads and 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 have 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 in FIG. 1 is a transmission type,
A light source 9 is provided. 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 ( (E.g., guest-host) type and (e) field sequential color type display method can be used. The driving method of the liquid crystal element using the liquid crystal composition of the present invention may be a passive driving type such as a segment type or a simple matrix type, a TFT (thin film transistor) type, a MIM (metal-insulator-metal) type and the like. May be an active drive type.

Further, the non-optically active ester compound of the present invention and the liquid crystal composition containing the compound may be used in fields other than display liquid crystal elements (for example, electronic materials such as non-linear optical function elements, capacitor materials, limiters, etc.). Application to electronics devices such as memory, amplifier, modulator, heat, light, pressure, mechanical deformation and voltage conversion device and sensor, power generation device such as thermoelectric generation device, spatial light modulation device, photoconductive material) It is possible.

[0064]

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. In addition, the symbols I, N, and
S _A , S _C , S _C ^* and C have the following meanings. I: Isotropic liquid N: Nematic phase S _A : Smectic A phase S _C : Smectic C phase S _C ^* : Chiral smectic C phase C: Crystal phase Further, the phase transition temperature in each production example and example is temperature controlled. The measurement was performed using a polarizing microscope equipped with a device and a DSC (differential scanning calorimeter).

Production Example 1 Production of 4-n-decyloxy-3-fluorobromobenzene 38.2 g of 4-bromo-2-fluorophenol (0.
2mol), potassium carbonate 27.6g, n-decyl bromide 48.6g (0.22mol), and N, N-
A mixture consisting of 80 ml of dimethylformamide at 80 ° C.
For 6 hours. Thereafter, the inorganic salt was separated by filtration, and 100 ml of toluene and 100 ml of 1 / 2N hydrochloric acid were added to perform a neutralization treatment. After the toluene phase was further washed with water and separated, toluene was distilled off from the toluene phase under reduced pressure.
The residue is distilled under reduced pressure, and 174 to 176 ° C./5.5 mmHg
To obtain 48.3 g of colorless oily 4-n-decyloxy-3-fluorobromobenzene.

Preparation Example 2: Preparation of 1- (4'-n-decyloxy-3'-fluorophenyl) -3-methyl-1-butyn-3-ol 4-n-decyloxy-3-fluorobromobenzene 2
To a mixture consisting of 9.79 g (0.09 mol), 12.1 g (0.144 mol) of 3-methyl-1-butyn-3-ol, 0.6 g of triphenylphosphine, 0.2 g of copper iodide and 20 g of diisopropylamine. Under a nitrogen atmosphere, 0.4 g of dichlorobis (triphenylphosphine) palladium was added, and the mixture was stirred at 40 ° C. for 1 hour. Thereafter, the mixture was heated and stirred at 60 ° C. for 1 hour and at 70 ° C. for 3 hours. The precipitated diisopropylamine hydrobromide was filtered off, and diisopropylamine was distilled off from the filtrate under reduced pressure. The residue was dissolved in toluene, neutralized with 1 / 2N hydrochloric acid, washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography, and 1- (4′-n-decyloxy-3′-
28.0 g of (fluorophenyl) -3-methyl-1-butyn-3-ol was obtained as a yellow oil.

Production Example 3: Production of 4-n-decyloxy-3-fluoro-1-ethynylbenzene 1- (4'-n-decyloxy-3'-fluorophenyl) -3-methyl-1-butyn-3-ol 26g
(0.078 mol) and 1.6 g of finely ground potassium hydroxide were added to 80 ml of toluene, the temperature was raised to 110 ° C., and the mixture was heated with stirring for 2 hours. Thereafter, the reaction mixture was filtered through celite to remove inorganic substances, toluene was distilled off, methanol was added to the residue, the methanol phase was separated, and methanol was distilled off under reduced pressure to give 4-n-decyloxy-. 16.5 g of 3-fluoro-1-ethynylbenzene was obtained as a light brown oil.

Production Example 4: 4-n-dodecyloxy-3-
Preparation of Fluorobromobenzene In Preparation Example 1, instead of using 48.6 g of n-decyl bromide, 54.8 g of n-dodecyl bromide was used.
According to the procedure described in Production Example 1 except that
-Dodecyloxy-3-fluorobromobenzene 60.
3 g were obtained (191-194 / 6 mmHg).

Production Example 5 Production of 1- (4'-n-dodecyloxy-3'-fluorophenyl) -3-methyl-1-butyn-3-ol In Production Example 2, 4-n-decyloxy-3- Instead of using 29.79 g of fluorobromobenzene, 4
-N-dodecyloxy-3-fluorobenzene 32.3
According to the procedure described in Production Example 2 except that g was used, 1-
(4'-n-dodecyloxy-3'-fluorophenyl) -3-methyl-1-butyn-3-ol 30.1 g
I got

Production Example 6: 4-n-dodecyloxy-3-
Production of Fluoro-1-ethynylbenzene In Production Example 3, 1- (4′-n-decyloxy-3 ′)
-Fluorophenyl) -3-methyl-1-butyne-3-
Described in Production Example 3 except that 28.2 g of 1- (4′-n-dodecyloxy-3′-fluorophenyl) -3-methyl-1-butyn-3-ol was used instead of 26 g of all. By following the procedure described above, 17.8 g of 4-n-dodecyloxy-3-fluoro-1-ethynylbenzene was obtained as a pale brown oil.

Production Example 7: Production of 4-tetrahydropyranyloxybromobenzene 51.9 g (0.3 mol) of 4-bromophenol,
30.2 g (0.36 mol) of 2,3-dihydropyran
A mixture consisting of chloroform and 120 g was cooled to 3 ° C. using an ice bath, and 0.03 g of p-toluenesulfonic acid monohydrate was added thereto, followed by stirring at the same temperature for 15 minutes. Thereafter, 2 g of sodium hydrogen carbonate and 3 parts of water were added to the reaction mixture.
0 g was added to stop the reaction, and the chloroform phase was separated. Chloroform was distilled off under reduced pressure, and n-
Hexane was added to obtain 70.2 g of 4-tetrahydropyranyloxybromobenzene as colorless crystals (melting point: 57 ° C).

Production Example 8: Production of 1- (4'-tetrahydropyranyloxyphenyl) -2- (4 "-n-decyloxy-3" -fluorophenyl) acetylene 4-tetrahydropyranyloxybromobenzene 5.1
4 g (0.02 mol), 4-n-decyloxy-3-
5.52 g of fluoro-1-ethynylbenzene (0.02 g)
mol), 0.20 g of triphenylphosphine, 40 mg of dichlorobis (triphenylphosphine) palladium
And a suspension consisting of 80 mg of copper iodide and 3 ml of tetrahydrofuran under a nitrogen atmosphere to a mixture consisting of 10 g of triethylamine and triethylamine. The mixture was heated and stirred. Thereafter, the precipitated triethylamine salt was filtered off,
Triethylamine was distilled off from the filtrate under reduced pressure. After adding toluene to the residue and washing with water, toluene was distilled off under reduced pressure, and n-hexane was added to the residue to give 1- (4'-tetrahydropyranyloxyphenyl) -2- (4 "-n-
5.66 g of decyloxy-3 ″ -fluorophenyl) acetylene was obtained as light brown crystals.

Production Example 9 Production of 1- (4'-hydroxyphenyl) -2- (4 "-n-decyloxy-3" -fluorophenyl) acetylene 1- (4'-tetrahydropyranyloxyphenyl)-
0.10 g of p-toluenesulfonic acid was added to a mixture consisting of 4.36 g of 2- (4 "-n-decyloxy-3" -fluorophenyl) acetylene, 15 g of chloroform and 15 g of methanol with stirring, and the mixture was stirred at room temperature for 1 hour. Stirred. Thereafter, chloroform and methanol were distilled off under reduced pressure, and ethyl acetate and water were added to the residue, followed by washing with water and liquid separation. After distilling off ethyl acetate from the organic phase, n-
Hexane was added and 1- (4'-hydroxyphenyl)
3.40 g of -2- (4 "-n-decyloxy-3" -fluorophenyl) acetylene was obtained as pale brown crystals.

Production Example 10 Production of 1- (4'-tetrahydropyranyloxyphenyl) -2- (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene In Production Example 8, 4-n-decyloxy According to the procedure described in Production Example 8, except that 6.08 g of 4-n-dodecyloxy-3-fluoro-1-ethynylbenzene was used instead of 5.52 g of -3-fluoro-1-ethynylbenzene, -(4'-tetrahydropyranyloxyphenyl) -2- (4 "-n-dodecyloxy-3"
6.68 g of -fluorophenyl) acetylene were obtained.

Production Example 11 Production of 1- (4'-hydroxyphenyl) -2- (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene In Production Example 9, 1- (4'-tetrahydropyrani Instead of using 4.36 g of (oxyphenyl) -2- (4 "-n-decyloxyphenyl) acetylene, 1-
(4′-tetrahydropyranyloxyphenyl) -2-
According to the procedure of Production Example 9, except that 4.64 g of (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene was used, 1- (4'-hydroxyphenyl)
3.59 g of -2- (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene was obtained.

Production Example 12: Production of 4-tetrahydropyranyloxy-3-fluorobromobenzene Instead of using 51.9 g of 4-bromophenol in Production Example 7, 57.3 g of 4-bromo-2-fluorophenol was used. Was used and the procedure described in Production Example 7 was followed to obtain 80.9 g of 4-tetrahydropyranyloxy-3-fluorobromobenzene.

Production Example 13: Production of 4-tetrahydropyranyloxy-3-fluoroethynylbenzene 55.0 g (0.2 mol) of 4-tetrahydropyranyloxy-3-fluorobromobenzene, 3-methyl-1
-Butyn-3-ol (25.2 g, 0.3 mol), triphenylphosphine 2.0 g, dichlorobis (triphenylphosphine) palladium 0.4 g, and diisopropylamine 100 g were added to a mixture of copper iodide 0.1 g under a nitrogen atmosphere. 8 g and tetrahydrofuran 10 m
was added and the temperature was raised to 75 ° C. over 1 hour. After heating and stirring at the same temperature for 3 hours, diisopropylamine was distilled off, toluene was added to the residue, and the precipitated inorganic salt was separated by filtration. Toluene was distilled off from the filtrate to obtain 4-tetrahydropyranyloxy-3-fluoro- (3′-hydroxy-3′-methylbutynyl) benzene as a pale brown oil. Next, the obtained 4-tetrahydropyranyloxy- (3'-hydroxy-3'-methylbutenyl) benzene and finely ground potassium hydroxide 3.4
g was added to 170 ml of toluene, heated to 110 ° C., and heated and stirred for 3 hours. Thereafter, the reaction mixture was filtered through celite to remove inorganic substances, toluene was distilled off, and the residue was distilled under reduced pressure to give 122 to 128 ° C / 5 mmHg.
To obtain 29.3 g of 4-tetrahydropyranyloxy-3-fluoroethynylbenzene.

Production Example 14: Production of 4-n-dodecylcarbonyloxyiodobenzene A mixture of 6.98 g of n-tridecanoic acid chloride, 6.6 g of 4-iodophenol and 20 ml of toluene was cooled in an ice bath and stirred. Triethylamine3.
3 g were added dropwise. Thereafter, the mixture was stirred at room temperature for one day, and the precipitated triethylamine hydrochloride was separated by filtration. The filtrate was neutralized with 1 / 2N hydrochloric acid, washed with water, and then the toluene phase was separated. The toluene was distilled off from the toluene solution under reduced pressure, and 4-
n-dodecylcarbonyloxyiodobenzene 10.7
3 g were obtained.

Production Example 15: Production of 4-n-octylcarbonyloxyiodobenzene In Production Example 14, n-tridecanoic acid chloride
9.20 g of 4-n-octylcarbonyloxyiodobenzene was obtained according to the procedure described in Production Example 14 except that 5.30 g of n-pelargonic acid chloride was used instead of 98 g.

Production Example 16: Production of 4-n-hexylcarbonyloxyiodobenzene In Production Example 14, n-tridecanoic acid chloride was used.
8.76 g of 4-n-hexylcarbonyloxyiodobenzene was obtained according to the procedure described in Production Example 14 except that 4.46 g of n-enanthic acid chloride was used instead of 98 g.

Production Example 17: 1- (4'-n-dodecylcarbonyloxyphenyl) -2- (4 "-hydroxy-
Production of 3 "-fluorophenyl) acetylene 4-n-dodecylcarbonyloxyiodobenzene 8.
32 g (0.02 mol), 4.4 g of 4-tetrahydropyranyloxy-3-fluoro-1-ethynylbenzene
(0.02 mol), triphenylphosphine 0.20
g, 40 mg of dichlorobis (triphenylphosphine) palladium and 10 g of triethylamine, a suspension of 80 mg of copper iodide and 3 ml of tetrahydrofuran was added under a nitrogen atmosphere.
The mixture was heated and stirred for 1 hour, then heated and stirred at 50 ° C for 1 hour and at 75 ° C for 4 hours. . Thereafter, the precipitated triethylamine salt was filtered off, and triethylamine was distilled off from the filtrate under reduced pressure. Toluene was added to the residue, and after washing with water, toluene was distilled off under reduced pressure.
(4′-n-dodecylcarbonyloxyphenyl) -2
-(4 "-tetrahydropyranyloxy-3" -fluorophenyl) acetylene as light brown crystals 7.41
g was obtained. Next, 1- (4'-n-dodecylcarbonyloxyphenyl) -2- (4 "-tetrahydropyranyloxy-3" -fluorophenyl) acetylene 5.08.
g, 15 g of chloroform and 15 g of methanol to a mixture of 0.10 p-toluenesulfonic acid under stirring.
g was added and stirred at room temperature for 1 hour. Thereafter, chloroform and methanol were distilled off under reduced pressure, and ethyl acetate and water were added to the residue, followed by washing with water and liquid separation. After the ethyl acetate was distilled off from the organic phase, n-hexane was added to give 1-
(4′-dodecylcarbonyloxyphenyl) -2-
4.00 g of (4 "-hydroxy-3" -fluorophenyl) acetylene was obtained as light brown crystals.

Production Example 18: 1- (4'-n-octylcarbonyloxyphenyl) -2- (4 "-hydroxy-
Preparation of 3 "-fluorophenyl) acetylene In Preparation Example 17, instead of using 8.32 g of 4-n-dodecylcarbonyloxyiodobenzene, 4-
n-octylcarbonyloxyiodobenzene 7.20
Except for using g, according to the procedure described in Production Example 17
1- (4'-n-octylcarbonyloxyphenyl)
-2- (4 "-hydroxy-3" -fluorophenyl)
3.57 g of acetylene was obtained as light brown crystals.

Production Example 19: 1- (4'-n-hexylcarbonyloxyphenyl) -2- (4 "-hydroxy-
Preparation of 3 "-fluorophenyl) acetylene In Preparation Example 17, instead of using 8.32 g of 4-n-dodecylcarbonyloxyiodobenzene, 4-
n-hexylcarbonyloxyiodobenzene 6.64
Except for using g, according to the procedure described in Production Example 17
1- (4'-n-hexylcarbonyloxyphenyl)
-2- (4 "-hydroxy-3" -fluorophenyl)
3.21 g of acetylene was obtained as light brown crystals.

Example 1 Preparation of Exemplified Compound 13 1- (4′-n-dodecylcarbonyloxyphenyl)
-2- (4 "-hydroxy-3" -fluorophenyl)
424 mg of acetylene, n-octyl bromide 212
mg, 138 mg of potassium carbonate and 3 ml of N, N-dimethylformamide were stirred with heating at 70 ° C. for 3 hours. Thereafter, the mixture was neutralized by adding 1 / 2N hydrochloric acid, and extracted with toluene. After washing the toluene solution with water, toluene is distilled off from the toluene solution under reduced pressure, the residue is purified by silica gel column chromatography (eluent: toluene), and the obtained solid is recrystallized twice from ethanol to give the exemplified compound. 466 mg of 13 were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 2 Preparation of Exemplified Compound 19 1- (4′-Hydroxyphenyl) -2- (4 ″ -n-
380 mg of dodecyloxy-3 ″ -fluorophenyl) acetylene, 158 mg of n-pelargonic acid, DCC20
A mixture of 6 mg and 5 g of chloroform was stirred at room temperature for 30 minutes, after which a catalytic amount of N, N-dimethylaminopyridine was added and stirred at room temperature for another 12 hours. Next, the generated solid was filtered off, the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (eluent: toluene), and recrystallized twice from ethanol to give Exemplified Compound 19 as a colorless product. 411 mg were obtained as crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 3 Preparation of Exemplified Compound 24 Exemplified compound 24 was prepared according to the procedure described in Example 2 except that 200 mg of n-lauric acid was used in place of 158 mg of n-pelargonic acid. 483 mg were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 4: Preparation of Exemplified Compound 31 In Example 1, 424 mg of 1- (4'-n-dodecylcarbonyloxyphenyl) -2- (4 "-hydroxy-3" -fluorophenyl) acetylene and n-octyl Instead of using 212 mg of bromide, 1-
(4'-n-octylcarbonyloxyphenyl) -2
368 mg of-(4 "-hydroxy-3" -fluorophenyl) acetylene and 165 n-hexylbromide
According to the procedure described in Example 1 except that mg was used, 366 mg of Exemplified Compound 31 as colorless crystals was obtained. The phase transition temperature (° C.) of this compound is shown below.

Example 5: Preparation of Exemplified Compound 58 In Example 1, 424 mg of 1- (4'-n-dodecylcarbonyloxyphenyl) -2- (4 "-hydroxy-3" -fluorophenyl) acetylene and n-octyl Instead of using 212 mg of bromide, 1-
(4'-n-hexylcarbonyloxyphenyl) -2
340 mg of-(4 "-hydroxy-3" -fluorophenyl) acetylene and 207 m of n-nonyl bromide
According to the procedure described in Example 1 except that g was used, 331 mg of Exemplified Compound 58 as colorless crystals was obtained. The phase transition temperature (° C.) of this compound is shown below.

Example 6: Preparation of Exemplified Compound 64 Exemplified Compound 64 was prepared in the same manner as in Example 2 except that 144 mg of n-caprylic acid was used instead of 158 mg of n-pelargonic acid. 385 mg were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 7 Preparation of Exemplified Compound 77 Exemplified compound 77 was prepared according to the procedure described in Example 2, except that 130 mg of n-enanthic acid was used in place of 158 mg of n-pelargonic acid. 364 mg were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 8: Preparation of Exemplified Compound 81 Exemplified Compound 81 was prepared according to the procedure described in Example 2 except that 228 mg of n-myristic acid was used in place of 158 mg of n-pelargonic acid. 507 mg were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 9: Preparation of Exemplified Compound 90 1- (4'-hydroxyphenyl) -2- (4 "-n-
Decyloxy-3 ″ -fluorophenyl) acetylene 3
A mixture of 52 mg, 207 mg of n-nonylchloroformate and 5 g of toluene was cooled in an ice bath, and 110 mg of triethylamine was added with stirring. Thereafter, the temperature was raised to room temperature, followed by stirring at room temperature for 6 hours. After neutralizing by adding 10 ml of 1/2 hydrochloric acid and separating a toluene phase, the toluene phase was washed with water and toluene was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) to give Exemplified Compound 90 as colorless crystals (355).
mg. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 10: Preparation of Exemplified Compound 100 In Example 2, 1- (4'-hydroxyphenyl)
Instead of using 380 mg of 2- (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene and 158 mg of n-pelargonic acid, 1- (4'-hydroxyphenyl) -2- (4 "-n- Decyloxy-3 "-
Exemplified compound 100 was converted to colorless crystals according to the procedure described in Example 2, except that 352 mg of (fluorophenyl) acetylene and 144 mg of n-caprylic acid were used.
5 mg were obtained. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 11: Preparation of Exemplified Compound 101 4-n-octylcarbonyloxyiodobenzene 37
4 mg, 4-n-decyloxy-3-fluoro-1-ethynylbenzene 276 mg, triphenylphosphine 1
A mixture of 0 mg, 10 mg of dichlorobis (triphenylphosphine) palladium, 8 mg of copper iodide and 4 g of triethylamine was heated and stirred at 40 ° C. for 1 hour under a nitrogen atmosphere, then heated at 50 ° C. for 1 hour and at 75 ° C. for 5 hours. Stirred. Thereafter, triethylamine was distilled off under reduced pressure, toluene was added to the residue, and after washing with water, toluene was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) to obtain 329 mg of Exemplified Compound 101 as colorless crystals. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 12 Preparation of Exemplified Compound 109 Exemplified compound 109 was prepared according to the procedure described in Example 2 except that 186 mg of n-undecanoic acid was used in place of 158 mg of n-pelargonic acid. 438 mg were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 13: Preparation of Exemplified Compound 117 Exemplified compound 117 was obtained in the same manner as in Example 1 except that 151 mg of n-pentyl bromide was used instead of 212 mg of n-octyl bromide. 387 mg were obtained as crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 14 Preparation of Exemplified Compound 120 Exemplified compound 120 was obtained in the same manner as in Example 1 except that 165 mg of n-hexyl bromide was used instead of 212 mg of n-octyl bromide. 348 mg were obtained as crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 15: Preparation of Exemplified Compound 124 Instead of using 372 mg of 4-n-octylcarbonyloxyiodobenzene in Example 11, 4-n-
According to the procedure described in Example 1 except that 416 mg of dodecylcarbonyloxyiodobenzene was used, 432 mg of Exemplified Compound 124 was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 16 Preparation of Exemplified Compound 126 The procedure of Example 1 was repeated, except that 272 mg of p-toluenesulfonic acid 2-n-butoxyethyl ester was used instead of 212 mg of n-octyl bromide. According to the operation, 308 mg of Exemplified Compound 126 was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 17: Preparation of Exemplified Compound 130 In Example 9, n-nonylchloroformate 207m
g instead of n-decyl chloroformate 22
Except that 1 mg was used, 365 mg of Exemplified Compound 130 was obtained as colorless crystals according to the procedure described in Example 9. The phase transition temperature (° C.) of this compound is shown below. still,(
The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 18: Preparation of Exemplified Compound 131 In Example 9, n-nonyl chloroformate 207m
n-octyl chloroformate 1 instead of using g
Except that 93 mg was used, 323 mg of Exemplified Compound 131 was obtained as colorless crystals according to the procedure described in Example 9.
The phase transition temperature (° C.) of this compound is shown below. still,
The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 19: Preparation of Exemplified Compound 132 In Example 9, 1- (4'-hydroxyphenyl)
Instead of using 352 mg of 2- (4 "-n-decyloxy-3" -fluorophenyl) acetylene and 207 mg of n-nonylchloroformate, 1- (4'-
Exemplified compound 13 according to the procedure described in Example 9 except that 380 mg of hydroxyphenyl) -2- (4 "-n-dodecyloxy-3" -fluorophenyl) acetylene and 193 mg of n-octylchloroformate were used.
418 mg of 2 were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the cooling process.

Example 20: Preparation of Exemplified Compound 135 150 mg of Exemplified Compound 101 produced in Example 11 was dissolved in 10 g of ethyl acetate, and 15 mg of 5% palladium / carbon (containing 50% by weight of water) was added under a nitrogen atmosphere. . Next, the inside of the system was set to a hydrogen atmosphere, and vigorously stirred at room temperature for 6 hours. Thereafter, palladium carbon was filtered off, ethyl acetate was distilled off from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: toluene) to obtain 136 mg of Exemplified Compound 135 as colorless crystals. The phase transition temperature (° C.) of this compound is shown below. In addition, ()
The numbers in the parentheses represent the phase transition temperatures during the cooling process.

Example 21: Preparation of Exemplified Compound 149 The procedure described in Example 20 was followed except that 150 mg of Exemplified Compound 101 was used in Example 20 instead of 150 mg of Exemplified Compound 120. 143 mg of Exemplified Compound 149 as colorless crystals
Obtained. The phase transition temperature (° C.) of this compound is shown below.

Example 22: Preparation of Exemplified Compound 158 The procedure described in Example 20 was followed except that 150 mg of Exemplified Compound 101 was used instead of 150 mg of Exemplified Compound 101 in Example 20. 122 mg of Exemplified Compound 158 was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 23: Preparation of Exemplified Compound 159 The procedure described in Example 20 was followed, except that 150 mg of Exemplified Compound 101 prepared in Example 12 was used instead of 150 mg of Exemplified Compound 101. 98 mg of Exemplified Compound 159 was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 24: Preparation of Exemplified Compound 171 The procedure described in Example 20 was followed, except that 150 mg of Exemplified Compound 101 was used instead of 150 mg of Exemplified Compound 101 in Example 20. 141 mg of Exemplified Compound 171 was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below. The numbers in parentheses indicate the phase transition temperatures during the temperature lowering process.

Example 25: Preparation of Exemplified Compound 180 The procedure described in Example 20 was followed, except that 150 mg of Exemplified Compound 101 prepared in Example 15 was used instead of 150 mg of Exemplified Compound 101. 137 mg of Exemplified Compound 180 as colorless crystals
Obtained. The phase transition temperature (° C.) of this compound is shown below.
The numbers in parentheses indicate the phase transition temperatures during the temperature lowering process.

Reference Example 1 Preparation of Liquid Crystal Composition The following compound group (Formula 11) was mixed at the ratio shown below, and heated and melted at 100 ° C. to obtain a liquid crystal composition (ferroelectric liquid crystal composition). Prepared.

[0110]

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Example 26: Preparation of liquid crystal composition To the liquid crystal composition prepared in Reference Example 1, 10% by weight of the exemplified compound 101 produced in Example 11 was added to prepare a liquid crystal composition.

Example 27: Production 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. An insulating orientation control layer (CRD-8616 manufactured by Sumitomo Bakelite Co., Ltd.) was spin-coated on the glass plate with the ITO film, and the film was baked at 90 ° C. for 5 minutes and at 200 ° C. for 30 minutes. 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. The cell was heated to 120 ° C. and heated (1
(20 ° C.), the liquid crystal composition prepared in Example 26 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. The driving characteristics at room temperature are summarized in Table 3 (Table 5).

The driving characteristics were measured in the following manner.・ Response time (τ10-90): ± 20 V,
A rectangular wave of 10 Hz was applied, the response under a polarizing microscope was detected by a light-multiplier tube, and the response time (transmission light amount 10% -90%) was determined with a digital oscilloscope. Tilt angle: A rectangular wave of ± 20 V, 1 Hz was applied to the liquid crystal element, 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 element, and the spontaneous polarization was determined by the triangular wave method. That is, the current accompanying the polarization reversal is converted into a voltage change by the current-voltage converter,
The integral value of the polarization reversal current was obtained from a digital oscilloscope. Threshold voltage: A rectangular wave of 180 Hz was applied to the liquid crystal element, the voltage was changed from ± 20 V to 0 V, and a value at which the transmitted light amount became 95% or less when ± 20 V was set as the threshold voltage. Θ-θm: Calculated from the difference between θ determined by the tilt angle and the memory angle (θm) when no electric field was applied.

Example 28: Preparation of liquid crystal composition To the liquid crystal composition prepared in Reference Example 1, 10% by weight of Exemplified Compound 31 produced in Example 4 was added to prepare a liquid crystal composition.

Example 29: Preparation of a liquid crystal element Example 27 was repeated except that the liquid crystal composition prepared in Example 28 was used instead of the liquid crystal composition prepared in Example 26. A liquid crystal element was produced according to the operation described in the above. When this liquid crystal element was held 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, under a polarizing microscope, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

Example 30: Preparation of liquid crystal composition The liquid crystal composition prepared in Reference Example 1 was added with 10% by weight of Exemplified Compound 13 prepared in Example 1 to prepare a liquid crystal composition.

Example 31: Preparation of a liquid crystal element Example 27 was described except that the liquid crystal composition prepared in Example 30 was used instead of the liquid crystal composition prepared in Example 26. A liquid crystal element was produced according to the operation described in above. When this liquid crystal element was held 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, under a polarizing microscope, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table 3. Example 32: Preparation of liquid crystal composition To the liquid crystal composition prepared in Reference example 1, 10% by weight of the exemplary compound 120 prepared in Example 14 was added. A liquid crystal composition was prepared.

Example 33: Preparation of a liquid crystal element Example 27 was repeated except that the liquid crystal composition prepared in Example 32 was used instead of the liquid crystal composition prepared in Example 26. A liquid crystal element was produced according to the operation described in the above. When this liquid crystal element was held 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, under a polarizing microscope, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. Table 3 summarizes the driving characteristics at room temperature. Comparative Example 1 A liquid crystal composition was prepared by adding 10% by weight of a compound represented by the following formula (Formula 12) to the liquid crystal composition prepared in Reference Example 1. did. Thereafter, the liquid crystal composition was injected into a liquid crystal cell manufactured by the same operation as in Example 27, to manufacture a liquid crystal element. When this liquid crystal element was held 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, under a polarizing microscope, a substantially uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

[0119]

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Comparative Example 2 A compound represented by the following formula (Formula 13) was added to the liquid crystal composition prepared in Reference Example 1 by 10% by weight to prepare a liquid crystal composition. Thereafter, the liquid crystal composition was injected into a liquid crystal cell manufactured by the same operation as in Example 27, to manufacture a liquid crystal element. This liquid crystal element was sandwiched between two polarizing plates arranged in a crossed Nicols state, and ± 20 V, 1
When a rectangular wave of 0 Hz was applied, a clear switching phenomenon was observed. In addition, under a polarizing microscope, a substantially uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

[0121]

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Comparative Example 3 A liquid crystal composition was prepared by adding 10% by weight of a compound represented by the following formula (Formula 14) to the liquid crystal composition prepared in Reference Example 1. Thereafter, the liquid crystal composition was injected into a liquid crystal cell manufactured by the same operation as in Example 27, to manufacture a liquid crystal element. When this liquid crystal element was sandwiched between two polarizing plates arranged in a crossed Nicols state and observed with a polarizing microscope, the precipitation of needle-like crystals in the liquid crystal was confirmed.

[0123]

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Reference Example 2 Preparation of Liquid Crystal Composition The following compound group (Chemical Formula 15) was mixed at the ratio shown below, and heated and melted at 100 ° C. to obtain a liquid crystal composition (ferroelectric liquid crystal composition). Prepared.

[0125]

Embedded image The phase transition temperature (° C.) of this liquid crystal composition is shown below.

Example 34: Preparation of a liquid crystal composition A liquid crystal composition was prepared by adding 15% by weight of the exemplified compound 180 prepared in Example 25 to the liquid crystal composition prepared in Reference Example 2.

Example 35: Preparation of a liquid crystal device Example 27 is the same as Example 27 except that the liquid crystal composition prepared in Example 34 was used instead of the liquid crystal composition prepared in Example 26. A liquid crystal element was produced according to the operation described in the above. When this liquid crystal element was held 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, under a polarizing microscope, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

Example 36: Preparation of liquid crystal composition A liquid crystal composition was prepared by adding 15% by weight of the exemplary compound 135 prepared in Example 20 to the liquid crystal composition prepared in Reference Example 2.

Example 37: Preparation of a liquid crystal device Example 27 was described except that the liquid crystal composition prepared in Example 36 was used instead of the liquid crystal composition prepared in Example 26. A liquid crystal element was produced according to the operation described in the above. When this liquid crystal element was held 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, under a polarizing microscope, a favorable uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

Comparative Example 4 A compound represented by the following formula (Formula 16) was added to the liquid crystal composition prepared in Reference Example 15 by 15% by weight to prepare a liquid crystal composition. Thereafter, the liquid crystal composition was injected into a liquid crystal cell manufactured by the same operation as in Example 27, to manufacture a liquid crystal element. This liquid crystal element was sandwiched between two polarizing plates arranged in a crossed Nicols state, and ± 20 V, 1
When a rectangular wave of 0 Hz was applied, a clear switching phenomenon was observed. In addition, under a polarizing microscope, a substantially uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. The driving characteristics at room temperature are summarized in Table-3.

[0131]

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[0132]

[Table 5]

From the comparison between Example 27, Example 29, Example 31, and Example 33 and Comparative Example 1 and Comparative Example 2,
It can be seen that by using the non-optically active ester compound of the present invention as a component of the liquid crystal composition, it becomes possible to improve the response speed of the liquid crystal composition and reduce θ-θm. Also, as compared with Comparative Example 1, it is found that the non-optically active ester compound of the present invention improves the response speed without narrowing the tilt angle. Further, comparison with Comparative Example 3 shows that the non-optically active ester compound of the present invention is excellent in compatibility with the liquid crystal composition. From the comparison between Example 35 and Example 37 and Comparative Example 4, the use of the non-optically active ester compound of the present invention showed that θ-
It can be seen that it is possible to reduce θm (bookshelf structure) and lower the threshold voltage.

[0134]

According to the present invention, it has become possible to provide a non-optically active ester compound useful as a component of a liquid crystal composition.

[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.

[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 source 8: polarizing plate 9: light source I ₀ : incident light I: transmitted light

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (Reference) C09K 19/18 C09K 19/18 19/46 19/46 G02F 1/13 500 G02F 1/13 500 (72) Inventor Hama Hideo 580-32 Nagaura, Sodegaura-shi, Chiba Prefecture Mitsui Chemicals, Inc. (72) Inventor Masakatsu Nakatsuka 580-32 Nagaura, Sodegaura-shi, Chiba Mitsui Chemicals Inc.F-term (reference) 4H006 AA01 AA03 AB64 BJ50 BM10 BM30 BM71 BP10 BP30 4H027 BA06 BD03 BD05 BD12 BD18 BD20 CB05 CC01 DK03

Claims (6)

[Claims] 1. A non-optically active ester compound represented by the general formula (1). Embedded image [Wherein, R ₁ and R ₂ each independently represent a linear or branched alkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom, or 3 carbon atoms which may be substituted with a halogen atom. To 24 linear or branched alkenyl groups, 3 to 2 carbon atoms which may be substituted with a halogen atom
4 straight-chain or branched-chain alkoxyalkyl group, or 3 to 2 carbon atoms which may be substituted with a halogen atom.
4 represents a linear or branched alkenyloxyalkyl group, Y ₁ represents a —COO— group or —OCOO— group, Y ₂ represents a single bond or —O— group, and Z represents —C≡C.
— Or —CH ₂ CH ₂ —. Wherein R ₁ and a straight-chain or branched-chain alkyl group having 3 to 24 carbon atoms which R ₂ does not contain an asymmetric carbon, or a straight-chain or branched 3 to 24 carbon atoms that does not contain an asymmetric carbon The non-optically active ester compound according to claim 1, which is a chain alkoxyalkyl group. 3. Y ₁ is a —COO— group, and Y ₂ is —O
The non-optically active ester compound according to claim 1 or 2, which is a group. 4. A liquid crystal composition comprising at least one non-optically active ester compound according to claim 1. 5. A liquid crystal comprising at least one kind of the non-optically active ester compound according to claim 1 and at least one kind of a compound represented by the following general formula (2). Composition. Embedded image [Wherein, R ₁₁ and R ₁₂ are each independently a linear or branched alkyl group having 3 to 24 carbon atoms, which may have an optically active asymmetric carbon, or a linear chain having 3 to 24 carbon atoms. Or a branched-chain alkenyl group or a straight-chain or branched-chain alkoxyalkyl group having 3 to 24 carbon atoms, wherein Y ₁₁ and Y ₁₂ are a single bond, a —COO— group or a bonding group selected from a —O— group Represents 6. A liquid crystal device using the liquid crystal composition according to claim 4 or 5.