JP2003096455A - Liquid-crystal composition and liquid-crystal element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a liquid-crystal composition enlarging the liquid crystal temperature, suppressing lowering of a tilt angle and realizing high-speed responsitivity at low temperatures, maintaining a bookshelf structure and a liquid-crystal element using the liquid crystal composition. SOLUTION: This liquid-crystal composition comprises at least one kind of naphthalene compound represented by general formula (1) (wherein, R11 and R12 denote each an alkyl group, an alkoxyalkyl group or the like; Y11 denotes a single bond or O; X11 and X12 denote each H or a halogen atom; and Y12 denotes COO, CH2 CH2 , OCH2 or the like) and an optically inactive thidiazole compound represented by general formula (2) (wherein, Y21 denotes a single bond or O; and X21 and X22 denote each H or a halogen atom). The liquid crystal element is obtained by using the composition.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel liquid crystal composition. More specifically, it relates to a liquid crystal composition useful as a constituent component of a liquid crystal element such as a display element and a liquid crystal element using the liquid crystal composition.

[0002]

2. Description of the Related Art Currently, a TN (twisted nematic) type display system is most widely used as a liquid crystal display device. This TN type display system is inferior in terms of response time to light emitting type devices (cathode tube, electroluminescence, plasma display, etc.).
STN (supermarket with a twist angle of 180-270 °)
Twisted nematic) display devices have also been developed, but the response time is still poor. Although various efforts have been made to improve the TN type display element having a short response time, it has not been realized yet.

However, in a new display method using a ferroelectric liquid crystal, which has been actively researched in recent years, there is a possibility that the response time is significantly improved [NAClark].
Applied Phys.lett., 36 , 899 (1980)].

This method is a method utilizing a chiral smectic phase such as a chiral smectic C phase exhibiting ferroelectricity. The phase showing ferroelectricity is chiral smectic C
Not only phase but chiral smectic F, G, H, I
It is known that such phase is a ferroelectric liquid crystal phase exhibiting ferroelectricity. These smectic liquid crystal phases belong to the tilt type chiral smectic phase, but in practice, the chiral smectic C, which has a low viscosity, is practically used.
Phases are preferred.

Various liquid crystal compounds exhibiting a chiral smectic C phase have been studied so far, and many compounds have already been searched and produced. However, many characteristics (high-speed response, orientation, high contrast ratio, memory stability, temperature dependence of these characteristics, etc.) required for application to the ferroelectric liquid crystal display element actually used are For optimization, at present, a ferroelectric liquid crystal composition obtained by mixing several liquid crystal compounds, which cannot be handled by one compound, is used.

Further, as the ferroelectric liquid crystal composition, not only a ferroelectric liquid crystal composition consisting of a compound exhibiting a ferroelectric liquid crystal phase but also a non-chiral smectic C is disclosed in JP-A-61-1195187. It has been reported that a compound or composition exhibiting a phase is used as a basic substance and one or a plurality of compounds exhibiting a ferroelectric liquid crystal phase are mixed with the basic substance to obtain the whole as a ferroelectric liquid crystal composition. Furthermore, a compound or composition showing a phase such as a smectic C phase is used as a basic substance, and one or a plurality of compounds which are optically active but do not show a ferroelectric liquid crystal phase are mixed to form a whole ferroelectric liquid crystal composition. You can also see reports (Mol.Cryst.Liq.Crys
t., 89, 327 (1982)).

In summary, by mixing one or more compounds that are optically active regardless of whether they exhibit a ferroelectric liquid crystal phase and a compound that exhibits a non-chiral phase such as a smectic C phase, It is understood that a ferroelectric liquid crystal composition can be constructed.

As described above, various compounds can be used as the constituents of the liquid crystal composition, but practically, a liquid crystal exhibiting a smectic C phase or a chiral smectic C phase in a wide temperature range including room temperature. Compounds or mixtures are desirable. As constituent components of these smectic C liquid crystal compositions, phenylbenzoate liquid crystal compounds, biphenyl liquid crystal compounds, phenylpyrimidine liquid crystal compounds and the like are known. However, it cannot be said that the liquid crystal composition containing these compounds as a constituent still has sufficient characteristics. For example, most of the chiral smectic C liquid crystal compositions that have been reported so far have a chevron structure (a layer structure bent in a “<” shape), and therefore, the response of spontaneous polarization to an applied electric field is large. It may not be performed efficiently and may cause an increase in response time, deterioration of memory property, and a decrease in contrast ratio due to zigzag alignment defects. Therefore, a liquid crystal material having a non-chiral or chiral smectic C phase having a bookshelf structure or a structure close thereto (pseudo bookshelf structure) is desired.

For example, JP-A-3-26785 discloses a naphthalene compound and a naphthalene compound having an asymmetric carbon represented by the following general formula (4) (Chemical formula 4). A liquid crystal composition containing a pyrimidine compound represented by Chemical formula 4) is disclosed, and a low viscosity bookshelf structure liquid crystal composition is obtained.

[0010]

[Chemical 4] (In the formula, R is an alkyl or alkoxy group having 6 to 16 carbon atoms, R'is 4 to 4 carbon atoms having at least one asymmetric carbon.
13 alkyl or alkoxy groups, R "and R"'
Represents an alkyl group having 6 to 16 carbon atoms)

However, when the naphthalene compound and the pyrimidine compound having the above asymmetric carbon are mixed with the naphthalene type liquid crystal, there are problems such as lowering of the upper limit of the liquid crystal temperature range and lowering of the tilt angle. Further, the smectic liquid crystal has a large temperature dependence of the response characteristic, and therefore, there is a problem that the response characteristic deteriorates (for example, an increase in threshold voltage) in a low temperature region (room temperature or lower).

Therefore, at present, it is necessary to maintain the bookshelf structure, suppress the decrease in the liquid crystal temperature range, maintain the required tilt angle, and improve the response characteristics at low temperatures. ..

[0013]

The object of the present invention is to realize a liquid crystal layer structure, orientation, and
It is intended to provide a liquid crystal composition in which various characteristics such as a liquid crystal temperature range and a tilt angle are improved, and a liquid crystal device using the liquid crystal composition.

[0014]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors have found a liquid crystal composition of a certain kind and arrived at the present invention. That is, the present invention relates to at least one kind of the naphthalene compound represented by the general formula (1) (formula 5) and at least one kind of the general formula (2).
The present invention relates to a liquid crystal composition containing a non-optically active thiadiazole compound represented by (Chemical Formula 6). Also,
The present invention relates to a liquid crystal element in which the liquid crystal composition is arranged between a pair of electrode substrates.

[0015]

[Chemical 5] [In the formula, R ₁₁ and R ₁₂ are a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, and 2 to 2 carbon atoms which may be substituted with a halogen atom.
A straight-chain or branched-chain alkoxyalkyl group having 4 or 3 to 2 carbon atoms which may be substituted with a halogen atom.
4 represents a linear or branched alkenyl group, R ₁₁ and R ₁₂ may have an optically active asymmetric carbon, and Y ₁₁
Represents a single bond or an —O— group, Y ₁₂ represents a —COO— group,
A —CH ₂ CH ₂ — group, a —OCH ₂ — or a —CH ₂ O— group, X ₁₁ and X ₁₂ represent a halogen atom or a hydrogen atom, and n represents 0 or 1.

[0016]

[Chemical 6] [In the formula, m and m'represent an integer of 1 to 20, Y ₂₁ represents a single bond or an -O- group, and X ₂₁ and X ₂₂ represent a hydrogen atom or a halogen atom.]

[0017]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.

The naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention is Y ₁₂
The following general formulas (1-A), (1-B),
They are roughly classified into four types, (1-C) and (1-D) (chemical formula 7).

[0019]

[Chemical 7] [In the formula, R ₁₁ and R ₁₂ , Y ₁₁ , X ₁₁ and X ₁₂ , n have the same meanings as in the general formula (1)]

In the liquid crystal composition of the present invention, the compound represented by the general formula (1
The naphthalene compounds represented by -A) to (1-D) may be used alone or in combination of two or more. It is preferably (1-A), (1-B) and / or (1-D), and more preferably (1-A) and / or (1-B).

When a plurality of naphthalene compounds represented by the general formula (1) are used in combination in the liquid crystal composition of the present invention, at least one of the naphthalene compounds represented by the general formula (1) is preferably (1 -A) and (1-
A) to (1-D) are used in combination, more preferably at least one of the naphthalene compounds represented by the general formula (1) is (1-A), and (1-
The naphthalene compound represented by A), (1-B) and / or (1-D) is used in combination.

In the naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention, R ₁₁ and R ₁₂ each have 1 to 1 carbon atoms which may be substituted with a halogen atom.
24 straight-chain or branched-chain alkyl group, C2-C24 straight-chain or branched-chain alkoxyalkyl group which may be substituted with a halogen atom, or C3 which may be substituted with a halogen atom To a linear or branched alkenyl group having 24 to 24 carbon atoms, preferably a linear or branched alkyl group having 3 to 20 carbon atoms which may be substituted with a halogen atom, or a halogen atom. It represents a good alkenyl group having 4 to 20 carbon atoms, and more preferably a linear or branched alkyl group having 4 to 15 carbon atoms which may be substituted with a halogen atom. In addition, when R ₁₁ and / or R ₁₂ is a branched chain group,
R ₁₁ and / or R ₁₂ may have an asymmetric carbon atom, and may further have an optically active asymmetric carbon atom.

When R ₁₁ and / or R ₁₂ have an optically active asymmetric carbon, both R ₁₁ and R ₁₂ may have an optically active asymmetric carbon, and only R ₁₁ has an optically active asymmetric carbon. It may have an asymmetric carbon atom, or only R ₁₂ may have an optically active asymmetric carbon atom. When the naphthalene compound represented by the general formula (1) having a wide liquid crystal temperature range is used for the purpose of widening the liquid crystal temperature range of the liquid crystal composition, R ₁₂ generally has an optically active asymmetric carbon. It is preferable to use a naphthalene compound represented by the formula (1).

In R ₁₁ and R ₁₂ , the halogen atom is preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom.

Specific examples of the group represented by R ₁₁ include, for example, methyl group, ethyl group, 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, 1-n
-Butylbutyl group, 1-methylpentyl group, 1-ethylpentyl group, 1-n-propylpentyl group, 1-n-butylpentyl group, 1-n-pentylpentyl group, 1-methylhexyl group, 1-ethylhexyl group , 1-n-propylhexyl group, 1-n-butylhexyl group, 1-n-
Pentylhexyl group, 1-n-hexylhexyl group, 1
-Methylheptyl group, 1-ethylheptyl group, 1-n-
Propylheptyl group, 1-n-butylheptyl group, 1-
n-pentylheptyl group, 1-n-heptylheptyl group, 1-methyloctyl group, 1-ethyloctyl group, 1
-N-propyloctyl group, 1-n-butyloctyl group, 1-n-pentyloctyl group, 1-n-hexyloctyl group, 1-n-heptyloctyl group, 1-n-octyloctyl group, 1-methylnonyl Group, 1-ethylnonyl group, 1-n-propylnonyl group, 1-n-butylnonyl group, 1-n-pentylnonyl group, 1-n-hexylnonyl group, 1-n-heptylnonyl group, 1-n-octyl group Nonyl group, 1-n-nonylnonyl group, 1-methyldecyl group, 2-methylpropyl group, 2-methylbutyl group, 2-
Ethylbutyl group, 2-methylpentyl group, 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-butylheptyl 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-dimeme Rubuchiru group, 2,3,3-trimethyl butyl group, a 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, Alkyl groups such as 3,5,5-trimethylhexyl group, 4-methylhexyl group, 6-methylheptyl group, 3,7-dimethyloctyl group and 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 Group, 3-fluoro-n-butyl group,
4-fluoro-n-butyl group, 3-fluoro-2-methylpropyl group, 2,3-difluoro-n-butyl group,
2,4-difluoro-n-butyl group, 3,4-difluoro-n-butyl group, 2-fluoro-n-pentyl group, 3
-Fluoro-n-pentyl group, 5-fluoro-n-pentyl group, 2,4-difluoro-n-pentyl group, 2,5
-Difluoro-n-pentyl group, 2-fluoro-3-methylbutyl group, 2-fluoro-n-hexyl group, 3-fluoro-n-hexyl group, 4-fluoro-n-hexyl group, 5-fluoro-n- Hexyl group, 6-fluoro-n
-Hexyl group, 2-fluoro-n-heptyl group, 4-fluoro-n-heptyl group, 5-fluoro-n-heptyl group, 2-fluoro-n-octyl group, 3-fluoro-n
-Octyl group, 6-fluoro-n-octyl group, 4-fluoro-n-nonyl group, 7-fluoro-n-nonyl group,
3-fluoro-n-decyl group, 6-fluoro-n-decyl group, 4-fluoro-n-dodecyl group, 8-fluoro-
n-dodecyl group, 5-fluoro-n-tetradecyl group,
9-fluoro-n-tetradecyl group,

2-chloroethyl 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-perfluorooctyl group, 1,1-dihydro-n-
Perfluorononyl group, 1,1-dihydro-n-perfluorodecyl group, 1,1-dihydro-n-perfluoroundecyl group, 1,1-dihydro-n-perfluorododecyl group, 1,1-dihydro -N-perfluorotetradecyl group, 1,1-dihydro-n-perfluoropentadecyl group, 1,1-dihydro-n-perfluorohexadecyl group,

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

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

2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5-methoxypentyl group, 6-methoxyhexyl group, 7-methoxyheptyl group, 8-methoxyoctyl group, 9-methoxynonyl group ,
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 Group, 9-ethoxynonyl group, 10-ethoxydecyl group, n-propyloxymethyl group, 2-n-propyloxyethyl group, 3-n-propyloxypropyl group, 4
-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 Base, 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 Group, 10-n-decyloxydecyl group, 2-n-undecyloxyethyl group,
4-n-undecyloxybutyl 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- (3'-ethylpentyloxy) butyl group, 5-
(3'-Ethylpentyloxy) pentyl group, 6-
(3'-Ethylpentyloxy) hexyl group, 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
-(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] ethoxy} ethyl 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, 1-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, 4- (2'-methoxyethoxy) butyl group, 4- (2'-ethoxyethoxy) butyl group, 4- (2'-isopropyloxyethoxy) butyl group, 4- (2'-isobutyloxyethoxy) ) Butyl group, 4- (2'-n-butyloxyethoxy) butyl group, 4- (2'-n-hexyloxyethoxy) butyl group, 4- (3'-n-propyloxypropoxy group) Oxy)
Butyl group, 4- (2'-n-propyloxy-1'-methylethoxy) butyl group, 4- [2 '-(2 "-methoxyethoxy) ethoxy] butyl group, 4- [2'-(2"
-N-butyloxyethoxy) ethoxy] butyl group, 4
-[2 '-(2 "-n-hexyloxyethoxy) ethoxy] butyl group, 5- (2'-n-hexyloxyethoxy) pentyl group, 2- [2'-(2" -n-butyloxyethoxy) ) Ethoxy] ethyl 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' , 5'-Trimethylhexyloxy) butyl group, 4- (3 ', 7'-dimethyloctyloxy) butyl group, 5- (2'-ethylhexyloxy) pentyl group, 5- (3', 5 ', 5' -Trimethylhexyloxy) pentyl group, 5- (3 ', 7'
-Dimethyloctyloxy) pentyl group, 6- (2'-
Ethylhexyloxy) hexyl group, 6- (3 ′,
5 ', 5'-trimethylhexyloxy) hexyl group,
Alkoxyalkyl groups such as 6- (3 ', 7'-dimethyloctyloxy) hexyl group, 2- (2'-trifluoromethylpropyloxy) ethyl group, 4- (2'-trifluoromethylpropyloxy) butyl group , 6- (2 '
-Trifluoromethylpropyloxy) hexyl group, 8
-(2'-trifluoromethylpropyloxy) octyl group, 2- (2'-trifluoromethylbutyloxy)
Ethyl group, 4- (2'-trifluoromethylbutyloxy) butyl group, 6- (2'-trifluoromethylbutyloxy) hexyl group, 8- (2'-trifluoromethylbutyloxy) octyl group, 2- (2'-trifluoromethylheptyloxy) ethyl group, 4- (2'-trifluoromethylheptyloxy) butyl group, 6- (2'-
Trifluoromethylheptyloxy) hexyl group, 8-
(2'-trifluoromethylheptyloxy) octyl group, 2- (2'-fluoroethyloxy) ethyl group, 4
-(2'-fluoroethyloxy) butyl group, 6-
(2'-Fluoroethyloxy) hexyl group, 8-
(2'-fluoroethyloxy) octyl group, 2-
(2'-fluoro-n-propyloxy) ethyl group, 4
A-(2'-fluoro-n-propyloxy) butyl group,
6- (2'-fluoro-n-propyloxy) hexyl group, 8- (2'-fluoro-n-propyloxy) octyl group, 2- (3'-fluoro-n-propyloxy)
Ethyl group, 4- (3'-fluoro-n-propyloxy) butyl group, 6- (3'-fluoro-n-propyloxy) hexyl group, 8- (3'-fluoro-n-propyloxy) octyl group , 2- (3'-fluoro-2'-
Methylpropyloxy) ethyl group, 4- (3′-fluoro-2′-methylpropyloxy) butyl group, 6-
(3'-Fluoro-2'-methylpropyloxy) hexyl group, 8- (3'-fluoro-2'-methylpropyloxy) octyl group, 2- (2 ', 3'-difluoro-
n-propyloxy) ethyl group, 4- (2 ′, 3′-difluoro-n-propyloxy) butyl group, 6-
(2 ', 3'-Difluoro-n-propyloxy) hexyl group, 8- (2', 3'-difluoro-n-propyloxy) octyl group, 2- (2'-fluoro-n-butyloxy) ethyl group , 4- (2'-fluoro-n-butyloxy) butyl group, 6- (2'-fluoro-n-butyloxy) hexyl group, 8- (2'-fluoro-n-butyloxy) octyl group, 2- (3 '-Fluoro-n-
Butyloxy) ethyl group, 4- (3'-fluoro-n-
Butyloxy) butyl group, 6- (3'-fluoro-n-
Butyloxy) hexyl group, 8- (3'-fluoro-n
-Butyloxy) octyl group, 2- (4'-fluoro-
n-butyloxy) ethyl group, 4- (4'-fluoro-
n-butyloxy) butyl group, 6- (4′-fluoro-
n-butyloxy) hexyl group, 8- (4'-fluoro-n-butyloxy) octyl group, 2- (2 ', 3'-
Difluoro-n-butyloxy) ethyl group, 4-
(2 ', 3'-difluoro-n-butyloxy) butyl group, 6- (2', 3'-difluoro-n-butyloxy) hexyl group, 8- (2 ', 3'-difluoro-n-
Butyloxy) octyl group, perfluoro (2-n-hexyloxyethyl) group,

1,1-dihydro-perfluoro (2-methoxyethyl) group, 1,1-dihydro-perfluoro (3-n-propyloxypropyl) group, 1,1-dihydro-perfluoro (2-ethoxy) 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-
(Butyloxy) octyl group and other alkoxyalkyl groups substituted with a halogen atom,

3-n-perfluoropropyl-2-propenyl group, 3-n-perfluorobutyl-2-propenyl group, 3-n-perfluoropentyl-2-propenyl group, 3-n-perfluorohexyl- Alkenyl group substituted by halogen atom such as 2-propenyl group, 3-n-perfluoroheptyl-2-propenyl group, 3-n-perfluorooctyl-2-propenyl group, 2-propenyl group, 2-butenyl group , 3-butenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2-
Hexenyl group, 3-hexenyl group, 4-hexenyl group,
5-hexenyl group, 2-heptenyl group, 3-heptenyl, 4-heptenyl group, 5-heptenyl group, 6-heptenyl, 2-octenyl group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6- Octenyl group, 7-
Octenyl group, 2-nonenyl group, 3-nonenyl group, 4-
Nonenyl group, 5-nonenyl group, 6-nonenyl group, 7-nonenyl group, 8-nonenyl group, 2-decenyl group, 3-decenyl group, 4-decenyl group, 5-decenyl group, 6-decenyl group, 7- Examples thereof include alkenyl groups such as decenyl group, 8-decenyl group, 9-decenyl group, and 3,7-dimethyl-6-octenyl group.

The above-mentioned specific examples have an asymmetric carbon atom.
Branched alkyl group, branched alkoxyalkyl group, branched alkyl
There is no description of the absolute configuration of the asymmetric carbon in the kenyl group.
Although not shown, it is represented by the general formula (1) used in the liquid crystal composition of the present invention.
Of naphthalene compounds ₁₁And R₁₂as,
The (R) -form, the (S) -form and the racemic form may be used depending on the purpose.
It can be selected and used.

When a plurality of naphthalene compounds represented by the general formula (1) are used in the liquid crystal composition of the present invention, R ₁₁ and R ₁₂ of the naphthalene compound represented by the general formula (1) are used.
May be the same or different.

In the naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention, Y ₁₁ represents a single bond or —O— group, Y ₁₂ represents —COO— group, —CH.
₂ CH ₂ - group, -OCH ₂ - represents a group or -CH ₂ O-group. Further, n represents 0 or 1, and X ₁₁ and X ₁₂ represent a halogen atom or a hydrogen atom. When n is 0, Y ₁₁ is preferably an —O— group, and when n is 1, it is preferably a single bond.

X ₁₁ and X ₁₂ represent a hydrogen atom or a halogen atom, preferably a fluorine atom, a chlorine atom, a bromine atom or a hydrogen atom, and more preferably a fluorine atom or a hydrogen atom. Further, the substitution positions of X ₁₁ and X ₁₂ are not particularly limited, but preferably,
X ₁₁ is ortho to Y ₁₁ , and X ₁₂ is ortho or meta to Y ₁₂ .

In the liquid crystal composition of the present invention, one kind of naphthalene compound represented by the general formula (1) may be used, or a plurality thereof may be used. Preferably, at least two types are used, and more preferably at least three types are used.

The naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention is described in, for example, JP-A-63-233932 and JP-A-09-263561.
Japanese Patent Laid-Open No. 09-227462, Japanese Patent Laid-Open No.
It can be manufactured according to the methods described in JP-A-130187 and JP-A-10-212263. Specific examples of the naphthalene compound represented by the general formula (1) used in the liquid crystal composition of the present invention include the following compounds (Table 1). Incidentally, n-C _p in Table H _{2p + 1} - group and _{-C p 'H 2p' + 1} -n group represents an alkyl group of straight chain, p and p 'is an integer of 1 to 24. Also, X ₁₁
The substitution position of is the ortho position to Y ₁₁ , and the substitution position of X ₁₂ is the meta position to Y ₁₂ .

[0045]

[Table 1]

[0046]

[0047]

[0048]

[0049]

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

In the non-optically active thiadiazole compound represented by the general formula (2) of the present invention, m and m ′ are 1 to
It represents an integer of 20, preferably an integer of 3 to 15, and more preferably an integer of 4 to 14. Y ₂₁ is-
It represents an O-group or a single bond, and preferably Y ₂₁ is a single bond. Further, X ₂₁ and X ₂₂ are a hydrogen atom or a halogen atom, preferably a hydrogen atom, a fluorine atom or a chlorine atom, and more preferably a hydrogen atom or a fluorine atom. Further, each of X ₂₁ and X ₂₂ may be a hydrogen atom, or each may be a halogen atom.

The substitution position of X ₂₁ and X ₂₂ is not particularly limited, but X ₂₁ is preferably an ortho position with respect to Y ₂₁ , and X ₂₂ is preferably with respect to the thiadiazole ring. It is the ortho position.

The non-optically active thiadiazole compound of the present invention is roughly classified into the following two types of structures (Chemical Formula 8) depending on the selection of the linking group of Y ₂₁ .

[0054]

[Chemical 8] [In the formula, m and m ′, X ₂₁ and X ₂₂ have the same meanings as in formula (2)] Preferably, it is (2-A).

In the liquid crystal composition of the present invention, the general formula (2)
The non-optically active thiadiazole compound represented by may be used alone or in combination of two or more. When a plurality of non-optically active thiadiazole compounds represented by general formula (2) are used in combination in the liquid crystal composition of the present invention, m and m ′ are the same in each non-optically active thiadiazole compound represented by general formula (2). Or may be different.

The non-optically active thiadiazole compound represented by the general formula (2) of the present invention can be produced, for example, according to the following process (Formula 9).

That is, hydrazine is allowed to act on the benzoic acid derivative represented by the general formula (A) (formula 9) (wherein X ′ represents a halogen atom or an alkoxy group), and the general formula (B) (formula 9) ) And the hydrazide represented by. afterwards,
The carboxylic acid derivative represented by the general formula (A ′) (Chemical formula 9) (wherein X ″ represents a halogen atom) is allowed to act on this hydrazide to give N represented by the general formula (C) (Chemical formula 9). -Acyl hydrazide, and then N represented by the general formula (C)
-Acyl hydrazide, phosphorus pentasulfide or 2,4-bis (4'-methoxyphenyl) -1,3-dithia-2,
4-diphosphetane-2,4-disulfide (law
The non-optically active thiadiazole compound represented by the general formula (2) can be produced by reacting it with Esson's reagent).

[0058]

[Chemical 9] [In the formula, m and m ′, Y ₂₁ , X ₂₁ and X ₂₂ have the same meanings as in the general formula (2), X ′ represents a halogen atom or an alkoxy group, and X ″ represents a halogen atom.)

General Use in Liquid Crystal Compositions of the Present Invention
Of the non-optically active thiadiazole compound represented by the formula (2)
As specific examples, the following compounds (Table 2) are listed.
You can get it. In the table, X_{twenty one}Is replaced by Y_{twenty one}
Ortho to X _{twenty two}The substitution position of is
Ortho position to the ring.

[0060]

[Table 2]

[0061]

The liquid crystal composition of the present invention comprises a liquid crystal containing at least one naphthalene compound represented by the general formula (1) and at least one non-optically active thiadiazole compound represented by the general formula (2). The weight ratio of the naphthalene compound represented by the general formula (1) and the non-optically active thiadiazole compound represented by the general formula (2) in the liquid crystal composition is not particularly limited. The weight ratio of the naphthalene compound represented by the general formula (1) to the non-optically active thiadiazole compound represented by the general formula (2) is preferably 40: 1 to 1: 6, more preferably 2
It is 0: 1 to 1: 3.

The liquid crystal composition of the present invention is further represented by the general formula (1) for the purpose of adjusting the temperature range of the liquid crystal phase and adjusting the response characteristics of the liquid crystal composition to an applied electric field. A liquid crystal compound and / or a non-liquid crystal compound other than the naphthalene compound and the non-optically active thiadiazole compound represented by the general formula (2) may be contained.

The liquid crystal compounds and / or non-liquid crystal compounds other than the naphthalene compound represented by the general formula (1) and the non-optically active thiadiazole compound represented by the general formula (2) are not particularly limited. However, for example, a phenylbenzoate compound represented by the general formula (3) (Chemical Formula 10),

[0065]

[Chemical 10] [In the formula, R ₃₁ and R ₃₂ represent a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, and R ₃₁ and R _{32 each} have an optically active asymmetric carbon atom. Y ₃₁ may be a single bond, —COO— group or —O.
Represents a -group, Y ₃₂ represents a -COO- group or a -O- group] A naphthalene compound represented by the general formula (6) (Chemical Formula 11),

[0066]

[Chemical 11] [In the formula, R ₄₁ and R ₄₂ represent a linear or branched alkyl group having 1 to 24 carbon atoms, R ₄₁ and R ₄₂ may have an optically active asymmetric carbon, and Y ₄₁ and Y ₄₂ is -O
A group or a single bond, X ₄₁ and X _{42 each} represent a hydrogen atom or a halogen atom, and z represents 0 or 1.] A biphenyl compound represented by the general formula (7) it can.

[0067]

[Chemical 12] [In the formula, R ₅₁ and R ₅₂ represent a linear or branched alkyl group having 1 to 24 carbon atoms, R ₅₁ and R ₅₂ may have an optically active asymmetric carbon, and Y ₅₁ and Y ₅₂ represents a single bond, an —O— group or a —COO— group, and X ₅₁ and X
₅₂ represents a hydrogen atom or a halogen atom, s and t represent 1 or 2, and at least one of s and t is 2. Preferably, the phenylbenzoate compound represented by the general formula (3) or the general formula ( It is a naphthalene compound represented by 6).

In the compounds represented by the general formula (3), the general formula (6) and the general formula (7), R ₃₁ , R ₃₂ , R ₄₁ ,
R ₄₂ , R ₅₁ and R ₅₂ represent a linear or branched alkyl group having 1 to 24 carbon atoms, and these groups may have an asymmetric carbon, and the asymmetric carbon is optically active. You may.
Preferably, R ₃₁ , R ₄₂ and R ₅₁ are linear alkyl groups having 3 to 15 carbon atoms, and R ₃₂ , R ₄₁ and R ₅₂ are alkyl groups having 4 to 12 carbon atoms having asymmetric carbon atoms. .

In the linear or branched alkyl group having 1 to 24 carbon atoms, specific examples thereof include R ₁₁ and R _12.
Examples of the alkyl group given as a specific example of can be given.

Y ₃₁ and Y ₃₂ represent a single bond, a --COO-- group or a --O-- group, preferably a --COO-- group or a --O-- group. Y ₄₁ and Y ₄₂ represent an —O— group or a single bond. Y ₅₁ and Y ₅₂ are a single bond, an —O— group or —
It represents a COO- group. X ₄₁ , X ₄₂ , X ₅₁ and X ₅₂ represent a hydrogen atom or a halogen atom, preferably a hydrogen atom or a fluorine atom. z represents 0 or 1, s and t represent 1 or 2, and at least one of s and t is 2.

When the compounds represented by the general formula (3), the general formula (6) and the general formula (7) are used in the liquid crystal composition of the present invention, these compounds may be used alone. Moreover, you may use together two or more. When a plurality of compounds represented by general formula (3), general formula (6) and general formula (7) are used in the liquid crystal composition of the present invention, each of general formula (3), general formula (6) and In the compound represented by the general formula (7), R ₃₁ , R ₃₂ , R ₄₁ , R ₄₂ , R ₅₁ and R ₅₂ may be the same or different.

The phenylbenzoate compound represented by the general formula (3) is described in, for example, JP-A-59-20250, JP-A-60-32748, and JP-A-61-21.
It can be produced according to the production method described in JP-A No. 0056 or JP-A No. 61-257948. The naphthalene compound represented by the general formula (6) can be produced, for example, according to the production method described in JP-A-63-233932. The biphenyl compound represented by the general formula (7) is described in, for example, JP-A-59-128357.
JP-A-60-23476, JP-A-60-3274
It can be produced according to the production method described in JP-A No. 8, JP-A-61-22051 or JP-A-61-30559.

In the liquid crystal composition of the present invention, the naphthalene compound represented by the general formula (1) and the general formula (2)
When a liquid crystal compound and / or a non-liquid crystal compound (hereinafter abbreviated as an additive component) other than the non-optically active thiadiazole compound represented by are used, the naphthalene compound represented by the general formula (1) and the non-optically active compound are used. The content of the additive component with respect to the mixture composed of the thiadiazole compound is not particularly limited, but preferably, the naphthalene compound represented by the general formula (1) and the non-optically active compound represented by the general formula (2) are used. The content of the thiadiazole compound is 99 to 15
% By weight, and the content of the additive component is 1 to 85% by weight, and more preferably the naphthalene compound represented by the general formula (1) and the non-optically active thiadiazole compound represented by the general formula (2). The content is 99 to 20% by weight, the content of the additive component is 1 to 80% by weight, and more preferably the naphthalene compound represented by the general formula (1) and the general formula (2). The content of the non-optically active thiadiazole compound is 98 to 25% by weight, and the content of the additive component is 2
~ 75% by weight.

The naphthalene compound represented by the general formula (1) and the general formula (2) used in the liquid crystal composition of the present invention.
A non-optically active thiadiazole compound represented by
The additive components include a compound exhibiting liquid crystallinity by itself and a compound exhibiting no liquid crystallinity. Further, a compound exhibiting liquid crystallinity includes a smectic C phase (hereinafter abbreviated as S _C phase) or a chiral smectic C phase (hereinafter, S S phase).
_C ^* phase) and a liquid crystallinity, but S
_Some compounds do not exhibit _C phase or S _C ^* phase. Each of these compounds can be effectively used as a constituent component of the liquid crystal composition of the present invention, but in the liquid crystal composition of the present invention, when an additive component is not used, according to the present invention,
At least one of the naphthalene compound represented by the general formula (1) and the non-optically active thiadiazole compound represented by the general formula (2) is a compound exhibiting an S _C phase or an S _C ^* phase. Preferably there is.

When an additive component is used in the liquid crystal composition of the present invention, the naphthalene compound represented by the general formula (1) according to the present invention and the non-optically active thiadiazole compound represented by the general formula (2), And, at least one of the added components is preferably a compound exhibiting a S _C phase or a S _C ^* phase.

The liquid crystal composition of the present invention causes a switching phenomenon when a voltage is applied, and can be applied to a liquid crystal display device using this which has a short response time. The liquid crystal composition of the present invention has a liquid crystal layer structure (bookshelf structure), orientation (bookshelf structure), temperature range of liquid crystal phase, viscosity (response time), as compared with conventionally known liquid crystal compositions.
Excellent in temperature dependence of viscosity (threshold voltage at low temperature), memory stability, and tilt angle.

Next, the liquid crystal element of the present invention will be described. The liquid crystal element of the present invention comprises the liquid crystal composition of the present invention arranged 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 arranged between a pair of substrates 2 each provided with a transparent electrode 3 and an insulating orientation control layer 4, and the layer thickness is set by a spacer 5. It is formed by connecting a pair of transparent electrodes 3 through a lead wire 6 so that a voltage can be applied from a power source 7. Further, the pair of substrates 2 is sandwiched by the pair of polarizing plates 8 arranged in a crossed Nicol state,
The light source 9 is arranged on the outer side of one side.

Examples of the material of the substrate 2 include glass such as soda lime glass and borosilicate glass, and transparent polymers such as polycarbonate, polyether sulfone and polyacrylate. The transparent electrode 3 provided on the two substrates 2 is, for example, In ₂ O ₃ , SnO ₂ or ITO (Indium tin oxide; Indiu).
A transparent electrode formed of a thin film of m Tin Oxide) is included.

The insulating orientation control layer 4 is for rubbing a polymer thin film such as polyimide with a flocked cloth such as nylon, acetate or rayon to orient 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, boron nitride containing hydrogen. , Cerium oxide, aluminum oxide, zirconium oxide, inorganic material insulating layer such as titanium oxide and magnesium fluoride, polyvinyl alcohol, polyimide, polyamide imide, polyester imide, polyether imide,
Organic materials such as polyetherketone, polyetheretherketone, polyethersulfone, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin, urea resin, acrylic resin An insulating layer may be used, and the insulating orientation control layer may have a two-layer structure in which an organic insulating layer is formed on an inorganic insulating layer, or an insulating orientation control layer composed only of an inorganic insulating layer or an organic insulating layer. May be.

When the insulating orientation control layer is an inorganic insulating layer, it can be formed by a vapor deposition method or the like. In the case of an organic insulating layer, an organic insulating layer material or a solution of its precursor 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,
It can be formed by removing the solvent under predetermined conditions (for example, under heating) and baking it if desired. 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, and γ-aminopropyltriethoxysilane, and then an organic insulating layer material or a precursor thereof. May be applied. The layer thickness of the insulating orientation control layer 4 is
Usually, 10 angstrom to 1 μm, preferably 1
0 to 3000 angstroms, more preferably 1
It is 0 to 1000 angstroms.

The two substrates 2 are kept at arbitrary intervals by the spacer 5. For example, silica beads or alumina beads having a predetermined diameter are sandwiched between the substrates 2 as spacers, and the two substrates 2 are hermetically sealed with a sealant (for example, an epoxy-based adhesive) so that the spacers are spaced at arbitrary intervals. 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 liquid crystal layer 1 is generally set to have a thickness of 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 source 7 by a lead wire. Further, on the outside of the substrate 2, a pair of polarizing plates 8 whose polarization axes are, for example, in a crossed Nicols state are arranged. The example of (Fig. 1) is transmissive,
A light source 9 is provided. Further, the liquid crystal element using the liquid crystal composition of the present invention can be applied not only as the transmissive element shown in (FIG. 1) but also as a reflective element.

The display system of the liquid crystal device using the liquid crystal composition of the present invention is not particularly limited,
For example, (a) helical variable distortion type, (b) SSFLC (surface stabilized ferro-electric liquid crystal) type, (c) TSM (transient scattering mode) type, (d) G-H ( A guest-host type display system and an (e) field sequential color type display system can be used.

The driving method of a 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. ) Type or the like may be used.

Further, the liquid crystal composition of the present invention is used in fields other than display liquid crystal devices (for example, electronic materials such as nonlinear optical function devices and capacitor materials, electronic devices such as limiters, memories, amplifiers and modulators, heat, It can be applied to light, pressure, mechanical deformation, and other voltage / voltage conversion elements and sensors, thermoelectric power generation elements such as power generation elements, spatial light modulation elements, and photoconductive materials.

[0087]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples. The symbols S _A and S _C in the examples and tables
^* Means the following. S _A : Smectic A phase S _C ^* : Chiral smectic C phase

The measurement in each example was carried out according to the method described below. Phase transition temperature: measured using a polarization microscope equipped with a temperature control device.・ Optical response time: ± 20 V, 10 Hz rectangular wave is applied to the liquid crystal element, the response under a polarizing microscope is detected by a photomultiplier, and the response time (transmitted light amount 10% -90%) is obtained from a digital oscilloscope. It was -Spontaneous polarization: A triangular wave of ± 20 V and 120 Hz was applied to the liquid crystal element, and the spontaneous polarization was obtained. That is, the current associated with the polarization reversal was converted into a voltage by a current-voltage converter, and the integrated value of the polarization reversal current was obtained from a digital oscilloscope. Tilt angle: A rectangular wave of ± 20 V and 1 Hz was applied to the liquid crystal element, and the angle (2θ) of the extinction positions at two points was visually determined under a polarizing microscope and calculated from this (2θ / 2). -Θ-θm: It was determined from the difference between θ obtained by the tilt angle and the memory angle (θm) when the electric field was not applied. The smaller this value,
Indicates that the layer structure is close to the bookshelf structure.・ Threshold voltage: 180Hz rectangular wave is applied to the liquid crystal element,
Voltage is changed from ± 20V to 0V, and the amount of transmitted light is ± 2
The voltage value at which the voltage becomes 95% or less when the voltage is 0 V is set as the threshold voltage. The smaller this voltage value, the lower the voltage that can be driven. The threshold voltage was measured under two temperature conditions of room temperature (25 ° C) and low temperature (5 ° C).

Reference Example 1: Preparation of Liquid Crystal Composition A The following compounds (Chemical Formula 13) were mixed in the ratios shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0090]

[Chemical 13]

Reference Example 2: Preparation of Liquid Crystal Composition B The following compound (Chemical Formula 14) was mixed in the ratio shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0092]

[Chemical 14]

Reference Example 3: Preparation of liquid crystal composition C
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0094]

[Chemical 15]

Reference Example 4: Preparation of Liquid Crystal Composition D The following compound (Chemical Formula 16) was mixed in the ratio shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0096]

[Chemical 16]

Reference Example 5: Preparation of liquid crystal composition E The following compound (Chemical Formula 17) was mixed in the ratio shown below,
The mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0098]

[Chemical 17]

Example 1: Preparation of liquid crystal composition To the liquid crystal composition A, the following compound (non-optically active thiadiazole compound) (Chemical formula 18) was added in an amount of 10% by weight to prepare 100
A liquid crystal composition (ferroelectric liquid crystal composition) was prepared by heating and melting at 0 ° C. and then cooling to room temperature.

[0100]

[Chemical 18]

Comparative Example 1: A compound other than the non-optically active thiadiazole compound according to the present invention was added to the naphthalene type liquid crystal. That is, 7% by weight of the following pyrimidine compound (P1) (Chemical formula 19) and 8% by weight of the following optically active naphthalene compound (N1) (Chemical formula 19) were added to the liquid crystal composition A, and 1
The mixture was heated and melted at 00 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0102]

[Chemical 19]

Example 2: Preparation of liquid crystal composition To liquid crystal composition B, the following compound (non-optically active thiadiazole compound) (Chemical Formula 20) was added in an amount of 7% by weight, and the mixture was heated to 100 ° C.
Then, the mixture was heated and melted at 1, then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition).

[0104]

[Chemical 20]

Example 3: Preparation of liquid crystal composition Liquid crystal composition C was mixed with the following compound (T-1) in an amount of 8% by weight.
(Non-optically active thiadiazole compound) (Chemical formula 21) and 12 wt% of the following compound (T-2) (Non-optically active thiadiazole compound) (Chemical formula 21) were added, and the mixture was heated and melted at 100 ° C., and then at room temperature. The mixture was cooled down to a liquid crystal composition (ferroelectric liquid crystal composition).

[0106]

[Chemical 21]

Example 4: Preparation of liquid crystal composition To liquid crystal composition D, the following compound (non-optically active thiadiazole compound) (Chemical Formula 22) was added in an amount of 10% by weight to prepare 100
A liquid crystal composition (ferroelectric liquid crystal composition) was prepared by heating and melting at 0 ° C. and then cooling to room temperature.

[0108]

[Chemical formula 22]

Example 5: Preparation of liquid crystal composition To liquid crystal composition E, the following compound (non-optically active thiadiazole compound) (Chemical Formula 23) was added in an amount of 10% by weight to prepare 100
A liquid crystal composition (ferroelectric liquid crystal composition) was prepared by heating and melting at 0 ° C. and then cooling to room temperature.

[0110]

[Chemical formula 23]

Example 6: Preparation of liquid crystal composition To liquid crystal composition C, the following compound (non-optically active thiadiazole compound) (Chemical formula 24) was added in an amount of 10% by weight to prepare 100
A liquid crystal composition (ferroelectric liquid crystal composition) was prepared by heating and melting at 0 ° C. and then cooling to room temperature.

[0112]

[Chemical formula 24]

Example 7: Preparation of liquid crystal composition Liquid crystal composition E was mixed with the following compound (T-3) in an amount of 5% by weight.
(Non-optically active thiadiazole compound) (Chemical formula 25) and the following compound (T-4) (optically active naphthalene compound) (Chemical formula 25) in an amount of 10% by weight were added, and the mixture was heated and melted at 100 ° C., and then allowed to reach room temperature. After cooling, a liquid crystal composition (ferroelectric liquid crystal composition) was prepared.

[0114]

[Chemical 25]

Example 8: Preparation of liquid crystal element Two 1.1 mm thick glass plates were prepared, an ITO film was formed on each glass plate, and surface treatment was further performed. CRD-8616 (manufactured by Sumitomo Bakelite Co., Ltd.) as an insulating orientation control layer was spin-coated on the glass plate with the ITO film so as to have a film thickness of 200 Å, and then baked at 90 ° C. for 1 hour and further 200 ° C. Firing for 1 hour. After cooling the glass plate to room temperature,
This orientation control layer is rubbed, and then one glass plate is sprinkled with silica beads having an average particle size of 1.9 μm, and two rubbed axes of the two glass plates are antiparallel to each other. The glass plate of No. 1 was pasted with a sealant to form a cell. Then replace this cell with 120
The liquid crystal compositions prepared in Examples 1 to 7 were heated to
What was heated to 0 ° C. was injected and cooled to room temperature at a temperature decreasing rate of 2 ° C./min. When this liquid crystal cell was placed in a polarization microscope in a crossed Nicols state and the alignment state was observed, a good uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. Further, the physical properties of the liquid crystal composition at room temperature (25 ° C.) and the threshold voltage at 5 ° C. were measured and are shown in (Table 3).

Comparative Example 3: Preparation of Liquid Crystal Element A cell was prepared by the same operation as that described in Example 8, and the liquid crystal compositions prepared in Reference Examples 1 to 5 and Comparative Example 1 were injected thereinto, It was cooled to room temperature at a temperature decrease rate of 2 ° C / min. When this liquid crystal cell was placed in a polarization microscope in a crossed Nicols state and the alignment state was observed, a good uniform alignment state was observed, and no alignment defects such as zigzag defects were observed. Further, the physical properties of the liquid crystal composition at room temperature (25 ° C.) and the threshold voltage at 5 ° C. were measured (Table 3).
I wrote it in.

As is clear from (Table 3), the liquid crystal composition of the present invention has an expanded upper limit temperature of the liquid crystal phase as compared with the liquid crystal compositions of Reference Examples 1, 2, 3, 4 and 5, and the tilt There is almost no decrease in angles, etc., and it is close to the ideal bookshelf structure as can be seen from the value of θ-θm,
Further, it can be seen that the threshold voltage at low temperature is also reduced.
Further, as compared with the liquid crystal composition of Example 1 and the liquid crystal composition of Comparative Example 1, the liquid crystal composition of the present invention expands the liquid crystal phase maximum temperature, the tilt angle is less lowered, and the θ-θm is smaller. It can be seen that the threshold voltage is also lowered.

[0118]

[Table 3]

[0119]

According to the present invention, it is possible to provide a high-speed response liquid crystal composition in which the bookshelf structure is maintained, the temperature range of the liquid crystal is expanded, and the decrease in tilt angle is suppressed.

[Brief description of 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 chiral smectic phase 2 substrates 3 transparent electrodes 4 Insulating orientation control layer 5 spacers 6 lead wire 7 power supply 8 Polarizer 9 light sources I0 incident light I transmitted light

   ─────────────────────────────────────────────────── ─── Continued front page    (72) Inventor Hidetaka Tsukada             Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture             Inside the company (72) Inventor Masakatsu Nakatsuka             Mitsui Chemicals Co., Ltd. 580-32 Nagaura, Sodegaura City, Chiba Prefecture             Inside the company F-term (reference) 4H027 BA06 BD02 BD04 BD08 BD12                       BD18 CC07 CC08 DJ01 DJ05                       DK03 DK07 DK08

Claims (6)

[Claims] 1. A naphthalene compound represented by the general formula (1) (formula 1): [In the formula, R ₁₁ and R ₁₂ are a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, and 2 to 2 carbon atoms which may be substituted with a halogen atom.
A straight-chain or branched-chain alkoxyalkyl group having 4 or 3 to 2 carbon atoms which may be substituted with a halogen atom.
4 represents a linear or branched alkenyl group, R ₁₁ and R ₁₂ may have an optically active asymmetric carbon, and Y ₁₁
Represents a single bond or an —O— group, Y ₁₂ represents a —COO— group,
A —CH ₂ CH ₂ — group, a —OCH ₂ — or a —CH ₂ O— group, X ₁₁ and X ₁₂ represent a hydrogen atom or a halogen atom, and n represents 0 or 1] at least one general formula ( 2) A liquid crystal composition comprising a non-optically active thiadiazole compound represented by (Chemical Formula 2). [Chemical 2] [In the formula, m and m'represent an integer of 1 to 20, Y ₂₁ represents a single bond or an -O- group, and X ₂₁ and X ₂₂ represent a hydrogen atom or a halogen atom.] 2. A non-optically active thiadi represented by the general formula (2).
Y of azole compound _{twenty one}The liquid according to claim 1, wherein is a single bond.
Crystal composition. 3. An optically active naphthalene compound represented by the general formula (1) at least two kinds.
Alternatively, the liquid crystal composition according to item 2. 4. The weight ratio of the naphthalene compound represented by the general formula (1) to the non-optically active thiadiazole compound represented by the general formula (2) in the crystal composition is 40: 1 to 1: 6. The liquid crystal composition according to claim 1, 2 or 3. 5. The liquid crystal composition according to claim 1, which contains at least one compound represented by the general formula (3) (formula 3). [Chemical 3] [In the formula, R ₃₁ and R ₃₂ represent a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, and R ₃₁ and R _{32 each} have an optically active asymmetric carbon atom. Y ₃₁ may be a single bond, —COO— group or —O.
Represents a group, Y ₃₂ is a single bond, a —COO— group or —O—
Represents a group] 6. A liquid crystal device comprising the liquid crystal composition according to claim 1, 2, 3, 4 or 5 disposed between a pair of electrode substrates.