JPH11152472A - Liquid crystal composition and liquid crystal device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid crystal composition capable of providing a ferroelectric liquid crystal device improved in various characteristics such as a liquid crystal temperature region or aligning properties by making the composition include a specific naphthylpyrimidine compound, a specified phenylpyrimidine compound or the like. SOLUTION: This composition contains (A) 10-60 wt.% of an optically inactive naphthylpyrimidine compound represented by the formula (R11 and R12 are each a (substituted)1-24C alkyl-(substituted)2-24C unsaturated alkyl; A11 and A12 are each a (substituted)1, 4-phenylene, pyridine-2,5-diyl or the like; X11 and X12 are each a single bond, COO or the like; Y11 and Y12 are each O, COO or the like], (B) 10-60 wt.% of an optically inactive phenylpyrimidine compound represented by formula II (R21 and R22 are each a 1-12C alkyl; Y21 and Y22 are each a single bond or O) and (C) 10-60 wt.% of an optically inactive thiadiazole compound represented by formula III (R31 and R32 are each a 1-12C alkyl; Y31 and Y32 are each a single bond or O).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

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

[0002]

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

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

The ferroelectric liquid crystal composition includes not only a ferroelectric liquid crystal composition comprising only a compound exhibiting a ferroelectric liquid crystal phase, but also a non-chiral smectic C in JP-A-61-195187. It has been reported that a compound or composition exhibiting a phase is used as a basic substance, and one or more compounds exhibiting a ferroelectric liquid crystal phase are mixed with the basic substance to obtain a ferroelectric liquid crystal composition as a whole. Further, a compound or composition showing a phase such as a smectic C phase is used as a basic substance, and one or more compounds which are optically active but do not show a ferroelectric liquid crystal phase are mixed to form a ferroelectric liquid crystal composition as a whole. There are also reports [Mol. Cryst. Liq. Cr
yst., 89, 327 (1982)]. To summarize these facts, 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, smectic C phase, or other compound, provide a ferroelectric substance. It turns out that a liquid crystal composition can be constituted.

As described above, various compounds can be used as constituents of the liquid crystal composition, but practically, a liquid crystal compound or a mixture exhibiting a smectic C phase in a wide temperature range including room temperature is desirable. . As the components of these smectic C liquid crystal compositions, phenylbenzoate-based liquid crystal compounds, phenylpyrimidine-based liquid crystal compounds, and the like are known. However, it cannot be said that the liquid crystal compositions containing these compounds as constituents still have sufficient properties. Therefore, at present, various tests are performed on materials exhibiting the smectic C phase, and the liquid crystal temperature range, the response time, the memory stability, the layer structure in the smectic C phase, the tilt angle, the alignment characteristics on the alignment film, etc. are optimized. It is necessary.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide a liquid crystal composition having improved characteristics such as a liquid crystal temperature range and orientation, and a use of the liquid crystal composition for practical use of a ferroelectric liquid crystal device. It is intended to provide a liquid crystal device having the above configuration.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found a certain kind of liquid crystal composition, and have reached the present invention. That is, the present invention relates to a non-optically active naphthylpyrimidine represented by at least one general formula (1) and a non-optically active non-optically active compound represented by at least one general formula (2) The present invention relates to a liquid crystal composition containing phenylpyrimidine and at least one non-optically active thiadiazole compound represented by the general formula (3). The present invention also relates to a liquid crystal device having the liquid crystal composition disposed between a pair of electrode substrates.

[0008]

Embedded image [Wherein, 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, or 2 to 24 carbon atoms which may be substituted with a halogen atom. And a non-adjacent —CH ₂ — group present in these groups (provided that Y ₁₁ ,
Y ₁₂ or -CH is bonded to an aromatic ring ₂ - group is excluded)
May be replaced by an oxygen atom, a sulfur atom, a —CO— group, a —COO— group or a —OCO— group, and A ₁₁ and A ₁₂ are a substituted or unsubstituted 1,4-phenylene group; A pyridine-2,5-diyl group or a trans-1,4-cyclohexylene group, X ₁₁ and X
₁₂ is a single bond, -COO- group, -OCO- group, -OCH ₂
— Or —CH ₂ O—, wherein Y ₁₁ and Y ₁₂ are —
Represents an O- group, a -COO- group or a -OCO- group,
b, p and q each represent 0 or 1]

[0009]

Embedded image [Wherein, R ₂₁ and R ₂₂ represent a linear or branched alkyl group having 1 to 12 carbon atoms, and Y ₂₁ and Y ₂₂ represent a single bond or an —O— group]

[0010]

Embedded image [Wherein, R ₃₁ and R ₃₂ represent a linear or branched alkyl group having 1 to 12 carbon atoms, and Y ₃₁ and Y ₃₂ represent a single bond or an —O— group]

[0011]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The liquid crystal composition of the present invention comprises at least one non-optically active naphthylpyrimidine represented by the general formula (1), at least one non-optically active phenylpyrimidine represented by the general formula (2), And a non-optically active thiadiazole compound represented by general formula (3). The non-optically active naphthylpyrimidine compound represented by the general formula (1) used in the liquid crystal composition of the present invention has the following general formula (1-) depending on the values of a, b, p, and q.
A) to (1-P) (Chemical formula 7).

[0012]

Embedded image In the liquid crystal composition of the present invention, the non-optically active naphthylpyrimidine compound represented by the general formula (1) is preferably
(1-A), (1-B), (1-C), (1-D),
(1-E), (1-F), (1-G), (1-H),
(1-I), (1-J), (1-M) or (1-N)
And more preferably (1-
B), (1-C), (1-F), (1-G), (1-
J) or (1-N).

In the liquid crystal composition of the present invention, the compound represented by the general formula (1)
The non-optically active naphthylpyrimidine compounds of -A) to (1-P) may be used alone or in combination of two or more. In the non-optically active naphthylpyrimidine compound represented by the general formula (1) used in the liquid crystal composition of the present invention, R ₁₁ and R ₁₂ are linear groups having 1 to 24 carbon atoms which may be substituted with a halogen atom. Or a branched-chain alkyl group, or an unsaturated alkyl group having 2 to 24 carbon atoms which may be substituted with a halogen atom;
Non-adjacent —CH ₂ — groups present in these groups (provided that —CH attached to Y ₁₁ , Y ₁₂ or an aromatic ring)
Excluding _2- group) is an oxygen atom, a sulfur atom, a -CO- group,
It may be replaced by a -COO- group or a -OCO- group.

Examples of the groups represented by R ₁₁ and R ₁₂ include: (1) a linear or branched alkyl group (hereinafter abbreviated as an alkyl group); (2) an alkyl group substituted with a halogen atom (hereinafter, an alkyl group) , abbreviated as haloalkyl group) (3) -CH ₂ - alkyl group is replaced by a sulfur atom - group an alkyl group of which is replaced by an oxygen atom (hereinafter, abbreviated as an alkoxyalkyl group) (4) -CH ₂ Group (hereinafter abbreviated as alkylthioalkyl group) (5) Alkyl group in which -CH ₂ -group is replaced by oxygen atom and substituted by halogen atom (hereinafter abbreviated as haloalkoxyalkyl group) (6)- CH ₂ - group is -CO- replaced alkyl group group (hereinafter, abbreviated as an alkylcarbonyl group) (7) -CH ₂ - alkyl group which group is replaced by -COO- group (hereinafter, alkylene Abbreviated as carbonyloxy group) (8) -CH ₂ - group is -OCO- alkyl group has been replaced with a group (hereinafter, abbreviated as alkoxycarbonylalkyl group) (9) straight-chain or branched unsaturated alkyl Group (hereinafter abbreviated as unsaturated alkyl group) (10) unsaturated alkyl group substituted with a halogen atom (hereinafter abbreviated as unsaturated haloalkyl group) (11) -CH ₂ -group is replaced with an oxygen atom Unsaturated alkyl group (hereinafter abbreviated as unsaturated alkoxyalkyl group) (12) An unsaturated alkyl group in which a —CH ₂ — group is replaced by an oxygen atom and substituted by a halogen atom (hereinafter, an unsaturated haloalkoxyalkyl group) Abbreviated as a group).

R ₁₁ and R ₁₂ are preferably an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkylthioalkyl group, an alkylcarbonylalkyl group, an alkoxycarbonylalkyl group, an alkylcarbonyloxyalkyl group or an unsaturated alkyl group. More preferably, they are an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkoxycarbonylalkyl group or an unsaturated alkyl group. R ₁₁ and R ₁₂ preferably have 4 to 20 carbon atoms, more preferably 5 to 15 carbon atoms.

Specific examples of R ₁₁ and R ₁₂ include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 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, 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-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 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-dimethylbutyl group, 2,3,3-trimethylbutyl group, 3-
Methylbutyl group, 3-methylpentyl group, 3-ethylpentyl group, 4-methylpentyl group, 2,3-dimethylpentyl group, 2,4-dimethylpentyl group, 2,4,4-
Trimethylpentyl, 2,3,3,4-tetramethylpentyl, 3-methylhexyl, 2,5-dimethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 3,5,5, -trimethylhexyl Groups, 4-methylhexyl group, 6-methylheptyl group, 3,7-dimethyloctyl group, alkyl groups such as 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, 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-
A chloro-n-octyl group, a 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-
n-perfluorohexadecyl group, 1,1,3-trihydro-n-perfluoropropyl group, 1,1,3-trihydro-n-perfluorobutyl group, 1,1,4-trihydro-n-perfluoro Butyl 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-perfluoro Octyl) 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-perfluoro Dodecyl) 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-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-
Haloalkyl groups such as (perfluoroethyl) heptyl group, 7- (n-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
A heptyloxydecyl group,

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

2-ethoxyethoxymethyl group, 2-n-
Butyloxyethoxymethyl group, 2-n-hexyloxyethoxymethyl group, 3-ethoxypropyloxymethyl group, 3-n-propyloxypropyloxymethyl group, 3-n-pentyloxypropyloxymethyl group,
3-n-hexyloxypropyloxymethyl group, 2-
Methoxy-1-methylethoxymethyl group, 2-ethoxy-1-methylethoxymethyl group, 2-n-butyloxy-1-methylethoxymethyl group, 4-methoxybutyloxymethyl group, 4-ethoxybutyloxymethyl group, 4
-N-butyloxybutyloxymethyl group, 2- (3 ′
-Methoxypropyloxy) ethyl group, 2- (3'-ethoxypropyloxy) ethyl group, 2- (1'-methyl-2'-methoxyethoxy) ethyl group, 2- (1'-methyl-2'-ethoxy) Ethoxy) ethyl group, 2- (1 ′
-Methyl-2'-n-butyloxyethoxy) ethyl group, 2- (4'-methoxybutyloxy) ethyl group, 2
-(4'-ethoxybutyloxy) ethyl group, 2-
[4 '-(2 "-ethylbutyloxy) butyloxy]
Ethyl group, 2- [4 '-(3 "-ethylpentyloxy) butyloxy] ethyl group, 3- (2'-methoxyethoxy) propyl group, 3- (2'-ethoxyethoxy)
Propyl group, 3- (2′-n-pentyloxyethoxy) propyl group, 3- (2′-n-hexyloxyethoxy) propyl group, 3- (3′-ethoxypropyloxy) propyl group, 3- (3 '-N-propyloxypropyloxy) propyl group, 3- (3'-n-butyloxypropyloxy) propyl group, 3- (4'-ethoxybutyloxy) propyl group, 3- (5'-ethoxypentyloxy ) Propyl, 4- (2′-methoxyethoxy) butyl, 4- (2′-ethoxyethoxy) butyl, 4- (2′-isopropyloxyethoxy) butyl, 4- (2′-isobutyloxyethoxy) ) Butyl group, 4- (2′-n-butyloxyethoxy) butyl group, 4- (2′-n-hexyloxyethoxy) butyl group, 4- (3′-n-propyloxypropyl) Oxy)
Butyl group, 4- (2'-n-propyloxy-1'-methylethoxy) butyl group, 4- [2 '-(2 "-methoxyethoxy) ethoxy] butyl group, 4- [2'-(2"
-N-butyloxyethoxy) ethoxy] butyl group, 4
-[2 '-(2 "-n-hexyloxyethoxy) ethoxy] butyl group, 5- (2'-n-hexyloxyethoxy) pentyl group, 2- [2'-(2" -n-butyloxyethoxy) ) Ethoxy] ethyl 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)
A hexyl group, an alkoxyalkyl group such as a 6- (3 ′, 7′-dimethyloctyloxy) hexyl group,

Methylthiomethyl, 2-methylthioethyl, 3-methylthiopropyl, 4-methylthiobutyl, 5-methylthiopentyl, 6-methylthiohexyl, 7-methylthioheptyl, 8-methylthiooctyl, 9 -Methylthiononyl group, 10-methylthiodecyl group, ethylthiomethyl group, 2-ethylthioethyl group, 3-ethylthiopropyl group, 4-ethylthiobutyl group, 5-ethylthiopentyl group, 6-ethylthiohexyl group 7-ethylthioheptyl, 8-ethylthiooctyl, 9-ethylthiononyl, 10-ethylthiodecyl, n-propylthiomethyl, 2-n-propylthioethyl, 3-n-propyl Thiopropyl group, 4-
n-propylthiobutyl group, 5-n-propylthiopentyl group, 6-n-propylthiohexyl group, 7-n-propylthioheptyl group, 8-n-propylthiooctyl group, 9-n-propylthiononyl Group, 10-n-propylthiodecyl group, n-butylthiomethyl group, 2-n-butylthioethyl group, 3-n-butylthiopropyl group, 4
-N-butylthiobutyl group, 5-n-butylthiopentyl group, 6-n-butylthiohexyl group, 7-n-butylthioheptyl group, 8-n-butylthiooctyl group, 9-
n-butylthiononyl group, 10-n-butylthiodecyl group, n-pentylthiomethyl group, 2-n-pentylthioethyl group, 3-n-pentylthiopropyl group, 4-n-
A pentylthiobutyl group, a 5-n-pentylthiopentyl group, a 6-n-pentylthiohexyl group, a 7-n-pentylthioheptyl group, an 8-n-pentylthiooctyl group,
9-n-pentylthiononyl group, 10-n-pentylthiodecyl group, n-hexylthiomethyl group, 2-n-hexylthioethyl group, 3-n-hexylthiopropyl group,
4-n-hexylthiobutyl group, 5-n-hexylthiopentyl group, 6-n-hexylthiohexyl group, 7-n
-Hexylthioheptyl group, 8-n-hexylthiooctyl group, 9-n-hexylthiononyl group, 10-n-hexylthiodecyl group, n-heptylthiomethyl group, 2-
n-heptylthioethyl group, 3-n-heptylthiopropyl group, 4-n-heptylthiobutyl group, 5-n-heptylthiopentyl group, 6-n-heptylthiohexyl group, 7-n-heptylthioheptyl Group, 8-n-heptylthiooctyl group, 9-n-heptylthiononyl group, 1
0-n-heptylthiodecyl group, octylthiomethyl group, 2-n-octylthioethyl group, 3-n-octylthiopropyl group, 4-n-octylthiobutyl group, 5-
n-octylthiopentyl group, 6-n-octylthiohexyl group, 7-n-octylthioheptyl group, 8-n-
Octylthiooctyl, 9-n-octylthiononyl, 10-n-octylthiodecyl, n-nonylthiomethyl, 2-n-nonylthioethyl, 3-n-nonylthiopropyl, 4- n-nonylthiobutyl group, 5-
n-nonylthiopentyl group, 6-n-nonylthiohexyl group, 7-n-nonylthioheptyl group, 8-n-nonylthiooctyl group, 9-n-nonylthiononyl group, 10-
n-nonylthiodecyl group, n-decylthiomethyl group, 2
-N-decylthioethyl group, 3-n-decylthiopropyl group, 4-n-decylthiobutyl group, 5-n-decylthiopentyl group, 6-n-decylthiohexyl group, 7-n
-Decylthioheptyl group, 8-n-decylthiooctyl group, 9-n-decylthiononyl group, 10-n-decylthiodecyl group, 2- (2'-ethylhexylthio) ethyl group, 2- (3 ', 5', 5'-trimethylhexylthio) ethyl group, 2- (3 ', 7'-dimethyloctylthio) ethyl group, 4- (2'-ethylhexylthio) butyl group, 4- (3', 5 ', 5'- Trimethylhexylthio) butyl group, 4- (3 ′, 7′-dimethyloctylthio) butyl group, 6- (2′-ethylhexylthio) hexyl group, 6- (3 ′, 5 ′, 5′-trimethylhexylthio) Alkylthioalkyl groups such as) hexyl group, 6- (3 ′, 7′-dimethyloctylthio) 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
A-(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-
A dihydro-perfluoro (2-methoxyethyl) group,
1,1-dihydro-perfluoro (3-n-propyloxypropyl) group, 1,1-dihydro-perfluoro (2-ethoxyethyl) group, 1,1-dihydro-perfluoro (2-n-pentyloxy) group Ethyl) 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'-trichloromethylbutyloxy) 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) B) 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 ′,
Haloalkoxyalkyl groups such as 3′-dichloro-n-butyloxy) octyl group,

A methylcarbonylmethyl group, a 2-methylcarbonylethyl group, a 3-methylcarbonylpropyl group,
4-methylcarbonylbutyl, 5-methylcarbonylpentyl, 6-methylcarbonylhexyl, 7-methylcarbonylheptyl, 8-methylcarbonyloctyl, 9-methylcarbonylnonyl, ethylcarbonylmethyl, 2-ethyl Carbonylethyl group, 3-ethylcarbonylpropyl group, 4-ethylcarbonylbutyl group, 5-ethylcarbonylpentyl group, 6-ethylcarbonylhexyl group, 7-ethylcarbonylheptyl group, 8-ethylcarbonyloctyl group, 9-ethylcarbonyl Nonyl group, n-propylcarbonylmethyl group, 2
-N-propylcarbonylethyl group, 3-n-propylcarbonylpropyl group, 4-n-propylcarbonylbutyl group, 5-n-propylcarbonylpentyl group, 6-
n-propylcarbonylhexyl group, 7-n-propylcarbonylheptyl group, 8-n-propylcarbonyloctyl group, 9-n-propylcarbonylnonyl group, n-
Butylcarbonylmethyl group, 2-n-butylcarbonylethyl group, 3-n-butylcarbonylpropyl group, 4-
n-butylcarbonylbutyl group, 5-n-butylcarbonylpentyl group, 6-n-butylcarbonylhexyl group, 7-n-butylcarbonylheptyl group, 8-n-butylcarbonyloctyl group, 9-n-butylcarbonylnonyl Group, n-pentylcarbonylmethyl group, 2-n-
Pentylcarbonylethyl group, 3-n-pentylcarbonylpropyl group, 4-n-pentylcarbonylbutyl group, 5-n-pentylcarbonylpentyl group, 6-n-
Pentylcarbonylhexyl group, 7-n-pentylcarbonylheptyl group, 8-n-pentylcarbonyloctyl group, 9-n-pentylcarbonylnonyl group, n-hexylcarbonylmethyl group, 2-n-hexylcarbonylethyl group, 3- n-hexylcarbonylpropyl group, 4
-N-hexylcarbonylbutyl group, 5-n-hexylcarbonylpentyl group, 6-n-hexylcarbonylhexyl group, 7-n-hexylcarbonylheptyl group, 8
Alkylcarbonylalkyl groups such as -n-hexylcarbonyloctyl group, 9-n-hexylcarbonylnonyl group,

Methylcarbonyloxymethyl group, 2-methylcarbonyloxyethyl group, 3-methylcarbonyloxypropyl group, 4-methylcarbonyloxybutyl group, 5-methylcarbonyloxypentyl group, 6-methylcarbonyloxyhexyl group, 7 -Methylcarbonyloxyheptyl group, 8-methylcarbonyloxyoctyl group, 9-methylcarbonyloxynonyl group, ethylcarbonyloxymethyl group, 2-ethylcarbonyloxyethyl group, 3-ethylcarbonyloxypropyl group, 4
-Ethylcarbonyloxybutyl group, 5-ethylcarbonyloxypentyl group, 6-ethylcarbonyloxyhexyl group, 7-ethylcarbonyloxyheptyl group, 8
-Ethylcarbonyloxyoctyl group, 9-ethylcarbonyloxynonyl group, n-propylcarbonyloxymethyl group, 2-n-propylcarbonyloxyethyl group, 3-n-propylcarbonyloxypropyl group, 4
-N-propylcarbonyloxybutyl group, 5-n-propylcarbonyloxypentyl group, 6-n-propylcarbonyloxyhexyl group, 7-n-propylcarbonyloxyheptyl group, 8-n-propylcarbonyloxyoctyl group, 9 -N-propylcarbonyloxynonyl group, n-butylcarbonyloxymethyl group, 2-n
-Butylcarbonyloxyethyl group, 3-n-butylcarbonyloxypropyl group, 4-n-butylcarbonyloxybutyl group, 5-n-butylcarbonyloxypentyl group, 6-n-butylcarbonyloxyhexyl group,
7-n-butylcarbonyloxyheptyl group, 8-n-
Butylcarbonyloxyoctyl group, 9-n-butylcarbonyloxynonyl group,

An n-pentylcarbonyloxymethyl group,
2-n-pentylcarbonyloxyethyl group, 3-n-
Pentylcarbonyloxypropyl group, 4-n-pentylcarbonyloxybutyl group, 5-n-pentylcarbonyloxypentyl group, 6-n-pentylcarbonyloxyhexyl group, 7-n-pentylcarbonyloxyheptyl group, 8-n- Pentylcarbonyloxyoctyl group, 9-n-pentylcarbonyloxynonyl group, n-
Hexylcarbonyloxymethyl group, 2-n-hexylcarbonyloxyethyl group, 3-n-hexylcarbonyloxypropyl group, 4-n-hexylcarbonyloxybutyl group, 5-n-hexylcarbonyloxypentyl group, 6-n- Hexylcarbonyloxyhexyl group,
7-n-hexylcarbonyloxyheptyl group, 8-n
-Hexylcarbonyloxyoctyl group, 9-n-hexylcarbonyloxynonyl group, n-heptylcarbonyloxymethyl group, 2-n-heptylcarbonyloxyethyl group, 3-n-heptylcarbonyloxypropyl group, 4-n-heptyl Carbonyloxybutyl group, 5-
n-heptylcarbonyloxypentyl group, 6-n-heptylcarbonyloxyhexyl group, 7-n-heptylcarbonyloxyheptyl group, 8-n-heptylcarbonyloxyoctyl group, 9-n-heptylcarbonyloxynonyl group, n- Octylcarbonyloxymethyl group, 2-n-octylcarbonyloxyethyl group, 3-
n-octylcarbonyloxypropyl group, 4-n-octylcarbonyloxybutyl group, 5-n-octylcarbonyloxypentyl group, 6-n-octylcarbonyloxyhexyl group, 7-n-octylcarbonyloxyheptyl group, 8- an n-octylcarbonyloxyoctyl group, a 9-n-octylcarbonyloxynonyl group,
n-nonylcarbonyloxymethyl group, 2-n-nonylcarbonyloxyethyl group, 3-n-nonylcarbonyloxypropyl group, 4-n-nonylcarbonyloxybutyl group, 5-n-nonylcarbonyloxypentyl group,
6-n-nonylcarbonyloxyhexyl group, 7-n-
Alkylcarbonyloxyalkyl groups such as nonylcarbonyloxyheptyl group, 8-n-nonylcarbonyloxyoctyl group, and 9-n-nonylcarbonyloxynonyl group;

Methyloxycarbonylmethyl, 2-methyloxycarbonylethyl, 3-methyloxycarbonylpropyl, 4-methyloxycarbonylbutyl, 5-methyloxycarbonylpentyl, 6-methyloxycarbonylhexyl, 7 -Methyloxycarbonylheptyl group, 8-methyloxycarbonyloctyl group, 9-methyloxycarbonylnonyl group, ethyloxycarbonylmethyl group, 2-ethyloxycarbonylethyl group, 3-ethyloxycarbonylpropyl group, 4
-Ethyloxycarbonylbutyl group, 5-ethyloxycarbonylpentyl group, 6-ethyloxycarbonylhexyl group, 7-ethyloxycarbonylheptyl group, 8
-Ethyloxycarbonyloctyl group, 9-ethyloxycarbonylnonyl group, n-propyloxycarbonylmethyl group, 2-n-propyloxycarbonylethyl group, 3-n-propyloxycarbonylpropyl group, 4
-N-propyloxycarbonylbutyl group, 5-n-propyloxycarbonylpentyl group, 6-n-propyloxycarbonylhexyl group, 7-n-propyloxycarbonylheptyl group, 8-n-propyloxycarbonyloctyl group, 9 -N-propyloxycarbonylnonyl group, n-butyloxycarbonylmethyl group, 2-n
-Butyloxycarbonylethyl group, 3-n-butyloxycarbonylpropyl group, 4-n-butyloxycarbonylbutyl group, 5-n-butyloxycarbonylpentyl group, 6-n-butyloxycarbonylhexyl group,
7-n-butyloxycarbonylheptyl group, 8-n-
Butyloxycarbonyloctyl, 9-n-butyloxycarbonylnonyl, n-pentyloxycarbonylmethyl, 2-n-pentyloxycarbonylethyl, 3-n-pentyloxycarbonylpropyl, 4
-N-pentyloxycarbonylbutyl group, 5-n-pentyloxycarbonylpentyl group, 6-n-pentyloxycarbonylhexyl group, 7-n-pentyloxycarbonylheptyl group, 8-n-pentyloxycarbonyloctyl group, 9 -N-pentyloxycarbonyl nonyl group,

An n-hexyloxycarbonylmethyl group,
2-n-hexyloxycarbonylethyl group, 3-n-
Hexyloxycarbonylpropyl group, 4-n-hexyloxycarbonylbutyl group, 5-n-hexyloxycarbonylpentyl group, 6-n-hexyloxycarbonylhexyl group, 7-n-hexyloxycarbonylheptyl group, 8-n- Hexyloxycarbonyloctyl group, 9-n-hexyloxycarbonylnonyl group, n-
Heptyloxycarbonylmethyl group, 2-n-heptyloxycarbonylethyl group, 3-n-heptyloxycarbonylpropyl group, 4-n-heptyloxycarbonylbutyl group, 5-n-heptyloxycarbonylpentyl group, 6-n- Heptyloxycarbonylhexyl group,
7-n-heptyloxycarbonylheptyl group, 8-n
-Heptyloxycarbonyloctyl group, 9-n-heptyloxycarbonylnonyl group, n-octyloxycarbonylmethyl group, 2-n-octyloxycarbonylethyl group, 3-n-octyloxycarbonylpropyl group, 4-n-octyl Oxycarbonylbutyl group, 5-
n-octyloxycarbonylpentyl group, 6-n-octyloxycarbonylhexyl group, 7-n-octyloxycarbonylheptyl group, 8-n-octyloxycarbonyloctyl group, 9-n-octyloxycarbonylnonyl group, n- Nonyloxycarbonylmethyl group,
2-n-nonyloxycarbonylethyl group, 3-n-nonyloxycarbonylpropyl group, 4-n-nonyloxycarbonylbutyl group, 5-n-nonyloxycarbonylpentyl group, 6-n-nonyloxycarbonylhexyl group, 7-n-nonyloxycarbonylheptyl group, 8
An alkoxycarbonylalkyl group such as -n-nonyloxycarbonyloctyl group, 9-n-nonyloxycarbonylnonyl group,

2-propenyl group, 2-butenyl group, 3-
Butenyl group, 2-pentenyl group, 3-pentenyl group, 4
-Pentenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 3-heptenyl, 4-heptenyl group, 5-heptenyl group, 6-heptenyl, 2-octenyl Group, 3-octenyl group, 4-octenyl group, 5-octenyl group, 6
-Octenyl group, 7-octenyl group, 2-nonenyl group,
3-nonenyl group, 4-nonenyl group, 5-nonenyl group, 6
-Nonenyl group, 7-nonenyl group, 8-nonenyl group, 2-
Decenyl group, 3-decenyl group, 4-decenyl group, 5-decenyl group, 6-decenyl group, 7-decenyl group, 8-decenyl group, 9-decenyl group, 2-butynyl group, 3-hexynyl group, 3- Heptynyl group, 4-heptynyl group, 5-heptynyl group, 7-octynyl group, 3,7-dimethyl-6
-Unsaturated alkyl group such as octenyl group, 3-n-perfluoropropyl-2-propenyl group, 3-n-perfluorobutyl-2-propenyl group, 3-n-perfluoropentyl-2-propenyl group, 3 Unsaturated haloalkyl groups such as -n-perfluorohexyl-2-propenyl group, 3-n-perfluoroheptyl-2-propenyl group and 3-n-perfluorooctyl-2-propenyl group;
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 '
Unsaturated alkoxyalkyl groups such as -propenyloxy) heptyl group, 8- (2'-propenyloxy) octyl group, 9- (2'-propenyloxy) nonyl group, and 10- (2'-propenyloxy) decyl group; 2- (2′-propenyloxy) -perfluoroethyl group, 3- (2 ′
-Propenyloxy) -perfluoropropyl group, 4-
(2′-propenyloxy) -perfluorobutyl group,
5- (2′-propenyloxy) -perfluoropentyl group, 6- (2′-propenyloxy) -perfluorohexyl group, 7- (2′-propenyloxy) -perfluoroheptyl group, 8- (2 ′ -Propenyloxy)-
Examples include an unsaturated haloalkoxyalkyl group such as a perfluorooctyl group. When a plurality of non-optically active naphthyl pyrimidine compounds represented by the general formula (1) are used in the liquid crystal composition of the present invention, R ₁₁ and R ₁₁ of the non-optically active naphthyl pyrimidine compound represented by the general formula (1) are used. R ₁₂ may be the same or different.

In the non-optically active naphthylpyrimidine compound represented by the general formula (1) of the present invention, A ₁₁ and A ₁₂
Represents a substituted or unsubstituted 1,4-phenylene group, pyridine-2,5-diyl group or trans-1,4-cyclohexylene group, wherein the substituent is a fluorine atom,
Examples include a halogen atom such as a chlorine atom and a bromine atom, or a cyano group, a nitro group, a methyl group, a trifluoromethyl group, a hydroxyl group, and the like. A ₁₁ and A ₁₂ are preferably a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a 1,4-phenylene group substituted by a hydroxyl group, a pyridine-2,5-diyl group or a trans-1,4 A cyclohexylene group, or an unsubstituted 1,4-phenylene group, a pyridine-2,5-diyl group or trans-
A 1,4-cyclohexylene group, more preferably,
A 1,4-phenylene group substituted by a fluorine atom or a hydroxyl group, or an unsubstituted 1,4-phenylene group, a pyridine-2,5-diyl group or a trans-1,4-cyclohexylene group. X ₁₁ and X ₁₂ are a single bond,-
COO—, —OCO—, —OCH ₂ — and —C
It represents a linking group selected from H ₂ O-group. Y ₁₁ and Y ₁₂
Represents a -O- group, a -COO- group or a -OCO- group. a, b, p and q each represent 0 or 1.
Specific examples of the non-optically active naphthylpyrimidine compound represented by the general formula (1) used in the present invention include the following compounds (Chemical Formulas 8 to 26).

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[0042]

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[0043]

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[0044]

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[0045]

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[0050]

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[0051]

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[0052]

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[0053]

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[0054]

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[0055]

Embedded image In the liquid crystal composition of the present invention, the non-optically active naphthylpyrimidine compound represented by the general formula (1) to be used may be produced by, for example, the production method described in JP-A No. 9-110837, pp. 63-70. Can be.

Next, the non-optically active phenylpyrimidine 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 phenylpyrimidine compound represented by the general formula (2), R ₂₁ and R ₂₂ represent a linear or branched alkyl group having 1 to 12 carbon atoms, and preferably have 4 to 11 carbon atoms. Represents a linear or branched alkyl group, and more preferably has 5 to 1 carbon atoms.
0 represents a linear alkyl group. Specific examples of the groups represented by R ₂₁ and R _22, for example, among the alkyl groups exemplified as specific examples of R ₁₁ and R _12, carbon atoms from 1 to 12
And the group of In the non-optically active phenylpyrimidine compound represented by the general formula (2), Y ₂₁ and Y ₂₂ represent a single bond or an —O— group. Non-optically active phenylpyrimidine compounds used in the liquid crystal composition of the present invention, depending on the type of Y ₂₁ and Y _22, the following (2-
A), (2-B), (2-C) or (2-D)
7) Four types of structures are adopted.

[0057]

Embedded image In the liquid crystal composition of the present invention, the non-optically active phenylpyrimidine compound represented by the general formula (2) is preferably
(2-C) or (2-D), more preferably
(2-C). Specific examples of the non-optically active phenylpyrimidine compound represented by the general formula (2) include, for example,
The following compounds (Chemical Formulas 28 to 31) can be exemplified.

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[0059]

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[0060]

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[0061]

Embedded image Some of the non-optically active phenylpyrimidine compounds represented by the general formula (2) used in the liquid crystal composition of the present invention can be obtained as commercial products, and can also be produced through the following steps. it can.

Production process of the non-optically active phenylpyrimidine compound represented by the general formula (2)
An acrolein derivative represented by 2) and a general formula (5)
A non-optically active phenylpyrimidine compound represented by the general formula (2) is produced by reacting an amidine derivative represented by the following formula (Formula 32) in the presence of a base (eg, sodium methoxide, sodium ethoxide). can do. Further, when Y ₂₁ and / or Y ₂₂ are —O— groups, if desired, R _{21 of the} acrolein derivative represented by the general formula (4) or the amidine derivative represented by the general formula (5) As R ₂₂ , a protecting group (for example, a benzyl group,
After the introduction of a tetrahydropyranyl group) to form a pyrimidine ring, it is also possible to remove the protecting group and introduce an R ₂₁ or R ₂₂ group.

[0063]

Embedded image In the liquid crystal composition of the present invention, as the non-optically active phenylpyrimidine compound represented by the general formula (2), only one type may be used, or a plurality of types may be used. When a plurality of non-optically active phenylpyrimidine compounds represented by the general formula (2) are used in the liquid crystal composition of the present invention, in each of the non-optically active phenylpyrimidine compounds represented by the general formula (2), R ₂₁ and / or R ₂₂ may be the same or different.

Next, the non-optically active thiadiazole compound represented by the general formula (3) 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 (3), R ₃₁ and R ₃₂ are
Represents a linear or branched alkyl group having 1 to 12 carbon atoms, preferably represents a linear or branched alkyl group having 1 to 11 carbon atoms, more preferably a linear alkyl group having 2 to 10 carbon atoms. Represents a group. Specific examples of the groups represented by R ₃₁ and R ₃₂ include, for example, groups having 1 to 12 carbon atoms among the alkyl groups exemplified as specific examples of R ₁₁ and R ₁₂ . In the non-optically active thiadiazole compound represented by the general formula (3), Y ₃₁ and Y ₃₂ represent a single bond or an —O— group.

The non-optically active thiadiazole compound used in the liquid crystal composition of the present invention is represented by the following (3-A), (3-B) or (3-C) depending on the type of Y ₃₁ and Y _32.
It has three types of structures shown in (Formula 33). In the liquid crystal composition of the present invention, the non-optically active thiadiazole compound represented by the general formula (3) is preferably (3-A) or (3-A).
B), and more preferably (3-A).

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Embedded image Specific examples of the non-optically active thiadiazole compound represented by the general formula (3) include, for example, compounds shown below (Chemical Formula 3)
4 to 38).

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[0071]

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The non-optically active thiadiazole compound represented by the general formula (3) used in the liquid crystal composition of the present invention is:
For example, it can be manufactured through the following steps.
That is, hydrazine is allowed to act on a benzoic acid derivative (wherein Z ₁ represents a halogen atom or an alkoxy group) represented by the general formula (6)
A hydrazide represented by 9). Thereafter, a benzoic acid halide represented by the general formula (8) (Chemical Formula 39) is allowed to act on this hydrazide, and N is represented by the general formula (9) (Chemical Formula 39).
—Acyl hydrazide. Then, phosphorus pentasulfide or 2,4-bis (4-methoxyphenyl) -1,3-
A non-optically active thiadiazole compound represented by the general formula (3) can be produced using dithia-2,4-diphosphetane-2,4-disulfide (lawesson's reagent).

[0073]

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The liquid crystal composition of the present invention comprises at least one non-optically active naphthylpyrimidine compound represented by the general formula (1) and at least one non-optically active phenylpyrimidine represented by the general formula (2) The liquid crystal composition contains a compound and at least one non-optically active thiadiazole compound represented by the general formula (3). The content is not particularly limited, but is preferably at least 1
The content of the non-optically active naphthylpyrimidine compound represented by the general formula (1) is 10 to 60% by weight, and the content of at least one non-optically active phenylpyrimidine compound represented by the general formula (2) is contained. The amount is 10-60% by weight,
The content of at least one non-optically active thiadiazole compound represented by the general formula (3) is 10 to 60% by weight. More preferably, the content of at least one non-optically active naphthylpyrimidine compound represented by the general formula (1) is 20 to 50% by weight, and at least one non-optically active naphthylpyrimidine compound represented by the general formula (2) The content of the active phenylpyrimidine compound is 20 to 50% by weight, and the content of at least one non-optically active thiadiazole compound represented by the general formula (3) is 20 to 50% by weight.

The liquid crystal composition of the present invention has a wider range of liquid crystals than conventionally known non-optically active liquid crystal compositions (for example, phenylpyrimidine non-optically active liquid crystal composition, phenylbenzoate liquid crystal composition). It is excellent in that it has a phase temperature range, excellent orientation, low viscosity, etc., and can provide a liquid crystal composition and a liquid crystal element having excellent performance when an optically active compound is added. It is.

The liquid crystal composition of the present invention is preferably a liquid crystal composition exhibiting a smectic C phase, and can be used as a ferroelectric liquid crystal composition. The liquid crystal composition of the present invention, the high temperature side, isotropic liquid, a nematic phase, a smectic A phase, a smectic C phase (hereinafter abbreviated to S _C phase) is characterized in that shows the phase sequence is Therefore, the alignment characteristics on the alignment film are excellent.

Next, the optically active compound to be added to the liquid crystal composition of the present invention, if desired, will be described. The optically active compound used in the liquid crystal composition of the present invention refers to a compound capable of forming an optically active liquid crystal composition when added to the liquid crystal composition of the present invention, and is preferably represented by the following general formula: It represents the compound represented by (10). R ₄₁ -Y ₄₁ -A ₄₁ -Y ₄₂ -R ₄₂ (10) [wherein, R ₄₁ and R ₄₂ are linear or branched alkyl having 1 to 24 carbon atoms which may be substituted with a halogen atom. Groups (non-adjacent —CH ₂ present in these groups)
The-group may be replaced by an oxygen, sulfur, -O-, -COO- or -OCO- group;
₄₁ and R ₄₂ may have an asymmetric carbon, the asymmetric carbon may be an optically active), or represents an optically active group (of 40) shown below,

[0078]

Embedded image (In the above formula, m represents an integer of 1 to 10, and r and s are 0
Or 1; t represents an integer of 0 to 4;
At least one of R ₄₁ and R ₄₂ represents an integer of 0;
It contains at least one optically active asymmetric carbon, and Y ₄₁ and Y ₄₂ are each a single bond, an —O— group, an —OCO— group, or —
Represents a COO- group, and A ₄₁ represents any of the following groups (Formula 41)]

[0079]

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Specific examples of R ₄₁ and R ₄₂ include the alkyl groups, haloalkyl groups, alkoxyalkyl groups, alkylthioalkyl groups, haloalkoxyalkyl groups, alkylcarbonyl groups, and alkylcarbonyloxyalkyl groups exemplified for R ₁₁ and R _12. And an alkoxycarbonylalkyl group, and a group in which the asymmetric carbon present in those groups is optically active, or an optically active group shown below (Formula 42).

[0081]

Embedded image (In the above formula, m, r, s, t and u represent the same meaning as described above.)

In the optically active compound used in the liquid crystal composition of the present invention, the absolute configuration of the optically active asymmetric carbon is not particularly limited.
The (S) -configuration may be used. The optical purity of the optically active asymmetric carbon is 0: 100 (100% ee) to 45:55 (10%) as the ratio between the (R) form and the (S) form.
ee) or 55:45 (10% ee) to 100:
A value of 0 (100% ee) is effectively used. Also,
Y ₄₁ and Y ₄₂ are a single bond, an —O— group, an —OCO— group,
Or a -COO- group. When an optically active compound is used as desired in the liquid crystal composition of the present invention, only one type of the optically active compound may be used, or a plurality of optically active compounds may be used in combination. The addition amount of the optically active compound is not particularly limited, but is preferably 1 to 40% by weight, more preferably 1 to 30% by weight, based on the liquid crystal composition of the present invention.
%, More preferably 1 to 20% by weight.

The non-optically active naphthylpyrimidine compound represented by the general formula (1), the non-optically active phenylpyrimidine compound represented by the general formula (2) and the general formula (3) used in the liquid crystal composition of the present invention. The non-optically active thiadiazole compound represented by the formula (1) includes a compound showing liquid crystallinity by itself and a compound not showing liquid crystallinity. Compounds exhibiting liquid crystallinity include compounds exhibiting an S _C phase,
Some compounds exhibit liquid crystallinity but do not exhibit the _SC phase. Each of these compounds can be effectively used as a component of the liquid crystal composition of the present invention. In the liquid crystal composition of the present invention, a non-optically active naphthylpyrimidine compound represented by the general formula (1), a non-optically active phenylpyrimidine compound represented by the general formula (2) and a non-optically active phenylpyrimidine compound represented by the general formula (3) It is preferable that at least one compound among the optically active thiadiazole compounds is a compound exhibiting an S _C phase. In the liquid crystal composition of the present invention, the optically active compound optionally used includes a compound exhibiting liquid crystallinity by itself and a compound not exhibiting liquid crystallinity. The compound exhibiting liquid crystallinity includes chiral smectic C Phase (hereinafter, S _C
^* Abbreviated as “phase”) and S _C
^{* Some} compounds show no phase. Each of these compounds can be effectively used as a component of the liquid crystal composition of the present invention.

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

The liquid crystal composition of the present invention causes a switching phenomenon when a voltage is applied, and can be applied to a liquid crystal display device having a short response time utilizing the switching phenomenon. The liquid crystal composition of the present invention, the response time as compared with the liquid crystal composition conventionally known, memory stability, layer structure in S _C phase, excellent in orientation characteristics in the tilt angle and orientation film ing.

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 illustrating an example of a liquid crystal element having a chiral smectic phase for describing a 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, and the layer thickness is set by a spacer 5. A connection is made between a pair of transparent electrodes 3 via a lead wire 6 so that a voltage can be applied from a power supply 7. Further, the pair of substrates 2 is sandwiched by a pair of polarizing plates 8 arranged in a crossed Nicols state, and a light source 9 is arranged outside one of them.

Examples of the material of the substrate 2 include glass such as soda lime glass and borosilicate glass, and transparent polymers such as polycarbonate, polyether sulfone, and polyacrylate. As the transparent electrode 3 provided on the two substrates 2, for example, In ₂ O ₃ , SnO ₂ or ITO (indium tin oxide; Indi)
um Tin Oxide). 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, or rayon to align the liquid crystal.

Examples of the insulating orientation control layer 4 include a silicon nitride, a silicon nitride containing hydrogen, a silicon carbide, a silicon carbide containing hydrogen, a silicon oxide, a boron nitride, and a boron nitride containing hydrogen. Substances, cerium oxide, aluminum oxide, zirconium oxide, inorganic substance insulating layer such as titanium oxide and magnesium fluoride, polyvinyl alcohol, polyimide, polyamide imide, polyester imide, polyether imide,
Organic materials such as polyether ketone, polyether ether ketone, polyether sulfone, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin, urea resin, acrylic resin, etc. An insulating orientation control layer having a two-layer structure in which an organic insulating layer is formed on an inorganic insulating layer, or an insulating orientation control layer consisting only of an inorganic insulating layer or an organic insulating layer. You may.

When the insulating orientation control layer is an inorganic insulating layer, it can be formed by an evaporation method or the like. In the case of an organic insulating layer, an organic insulating layer material or a solution of a precursor thereof is 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, and Removing the solvent under the conditions of (for example, under heating),
It can be formed by firing if desired. When forming the organic insulating layer, 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) -γ-aminopropyltriethoxysilane, γ Surface treatment may be performed using a silane coupling agent such as -aminopropyltrimethoxysilane or γ-aminopropyltriethoxysilane, and then an organic insulating layer material or a precursor thereof may be applied. Insulating orientation control layer 4
Is usually 10 Å to 1 μm, preferably 10 to 3,000 Å, and more preferably 10 to 1,000 Å.

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 used as spacers on the substrate 2.
By sealing the periphery of the two substrates 2 with a sealant (for example, an epoxy-based adhesive), it is possible to maintain an arbitrary interval. 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 generally has a thickness of 0.5 to 20 μm.
m, preferably 1-5 μm, more preferably 1-3
Set to a thickness of μm. The transparent electrode 3 is connected to an external power supply 7 by a lead wire. Outside the substrate 2, a pair of polarizing plates 8 whose polarization axes are in, for example, a crossed Nicols state are arranged. The example shown in FIG. 1 is of a transmission type and includes a light source 9. Further, the liquid crystal device using the liquid crystal composition of the present invention can be applied not only as a transmissive device shown in FIG. 1 but also as a reflective device.

The display system of the liquid crystal device using the liquid crystal composition of the present invention is not particularly limited, but
For example, (a) helical distortion type, (b) SSFLC (surface stabilized ferroelectric liquid crystal) type, (c) TSM (transient scattering mode) type, (d) GH ( A guest-host type display scheme can be used.
Further, the liquid crystal composition of the present invention may be used in fields other than display liquid crystal devices (for example, nonlinear optical function devices, electronic materials such as capacitor materials, limiters, memories,
Electronics elements such as amplifiers and modulators, heat,
Light, pressure, mechanical deformation and voltage conversion elements and sensors,
It can be applied to a power generation element such as a thermoelectric power generation element.

[0092]

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. Incidentally, the symbols I, N, Ch, S _A , S
_C , S _C ^* and C represent the following meanings. I: isotropic liquid N: nematic phase Ch: cholesteric phase (chiral nematic phase) S _A: smectic A phase S _C: smectic C phase S _C ^*: chiral smectic C phase C: crystal phase

The measurement in each example was performed according to the following method. -Phase transition temperature: Measured using a polarizing microscope equipped with a temperature controller and a differential scanning calorimeter. Optical response time: ± 20 V, 10 Hz rectangular wave is applied to the liquid crystal cell, the response of the liquid crystal cell under a polarizing microscope is detected using a photomultiplier tube, and the response time (transmission light amount 10%) is obtained from a digital oscilloscope. -90%). Tilt angle: ± 20 V, 1 Hz rectangular wave was applied to the liquid crystal cell, and the angle (2θ) of the extinction position at two points was visually determined under a polarizing microscope, and the angle was calculated (2θ / 2). Spontaneous polarization: A triangular wave of ± 20 V, 120 Hz was applied to the liquid crystal cell, and the spontaneous polarization was determined by a triangular wave method. That is, the current accompanying the polarization reversal 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. -Memory stability: 200 μs, ± 20 for liquid crystal cell
V, and was obtained from the retention of the amount of transmitted light when a bipolar pulse (FIG. 2) with a duty ratio of 1: 200 was applied. The larger this value is, the higher the memory stability is. ΔT: ± 20 V in the liquid crystal cell, duty ratio 1:20
A bipolar pulse of 0 was applied, and the value was obtained from the pulse width at the time when the memory stability became 80%. The smaller this value is,
This means that driving with short pulses is possible. -Contrast ratio: ± 20 V, 10 Hz rectangular wave is applied to the liquid crystal cell, and the response of the liquid crystal cell under a polarizing microscope is
It was detected using a photomultiplier tube, and determined from the output difference (mv) between the photomultiplier tube in the bright state and the dark state. The larger this value is, the higher the contrast ratio is.

Example 1 Preparation of Liquid Crystal Composition The following compound group (Chemical Formula 43) was mixed at the following ratio, melted at 100 ° C., and then cooled to room temperature.
A liquid crystal composition was prepared. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → N → S A →} S c → C 99 89 86 10 ℃ below

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Example 2 Preparation of Liquid Crystal Composition The following compound group (Formula 44) was mixed at the following ratio, melted by heating at 100 ° C., and then cooled to room temperature.
A liquid crystal composition was prepared. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → N → S A →} S c → C 98 87 80 10 ℃ below

[0097]

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Comparative Example 1 For comparison, a liquid crystal composition containing no non-optically active naphthylpyrimidine compound represented by the general formula (1) was prepared. That is, the following compound group (Formula 45) was mixed at the ratio shown below, and heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → N → S A →} S c → C 84 73 70 10 ℃ below

[0099]

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Comparative Example 2 For comparison, a liquid crystal composition containing no non-optically active naphthylpyrimidine compound represented by the general formula (1) was prepared. That is, the following compound group (Chemical Formula 46) was mixed at the ratio shown below, heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → N → S A →} S c → C 82 70 68 10 ℃ below

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Comparative Example 3 For comparison, a liquid crystal composition containing no non-optically active phenylpyrimidine compound represented by the general formula (2) was prepared. That is, the following compound group (Chemical Formula 47) was mixed at the ratio shown below, heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. This liquid crystal composition crystallized at room temperature.

[0103]

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Comparative Example 4 For comparison, a liquid crystal composition containing no non-optically active thiadiazole compound represented by the general formula (3) was prepared. That is, the following compound group (Chemical Formula 48) was mixed at the ratio shown below, heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. The phase transition temperature of this liquid crystal composition is shown below. _{· I → N → S A →} S c → C 78 75 61 10 ℃ below

[0105]

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Example 3 Preparation of Liquid Crystal Composition An optically active compound was added to the liquid crystal composition prepared in Example 1 to prepare a liquid crystal composition (ferroelectric liquid crystal composition). That is, an optically active compound represented by the following formula (11) (Formula 49) was added to the liquid crystal composition prepared in Example 1 for 7.
0 wt% was added, and the mixture was heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 89 65 56 10 ℃ below

[0107]

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Example 4 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. XL-1400 [polyimide (Hitachi Chemical Co., Ltd.) was used as an insulating orientation control layer on the glass plate with the ITO film.
Manufactured) was spin-coated so as to have a thickness of 200 Å, and then baked at 90 ° C. for 1 hour, and further baked at 200 ° C. for 1 hour. After cooling the glass plate to room temperature, this orientation control layer is subjected to a rubbing treatment. Thereafter, silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates, and the rubbing treatment shafts of the two glass plates are separated. Were bonded to each other using a sealing agent so that the cells were antiparallel to each other, thereby producing a cell. Thereafter, the cell was heated to 120 ° C., and the liquid crystal composition prepared in Example 3 was heated to 120 ° C., and injected.
The mixture was cooled to room temperature at a cooling rate of 1 minute to produce a liquid crystal element.
When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, a favorable uniform alignment state was observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 1 (Table 1).

Comparative Example 5 As a comparison, the liquid crystal composition prepared in Comparative Example 1 was added with the formula (1)
7% by weight of the optically active compound represented by 1) was added,
After heating and melting at 0 ° C., the mixture was cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 75 67 58 10 ℃ less then prepared two 1.1mm thick glass plate, on each of the glass plates, to form an ITO film, further Surface treatment was performed. XL-1400 [polyimide (manufactured by Hitachi Chemical Co., Ltd.)] is spin-coated on the glass plate with the ITO film so as to have a thickness of 200 Å as an insulating orientation control layer. The firing was performed for 200 hours, and then the firing was performed at 200 ° C. for 1 hour. After cooling the glass plate to room temperature, this orientation control layer is subjected to a rubbing treatment. Thereafter, silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates, and the rubbing treatment shafts of the two glass plates are separated. Were bonded to each other using a sealing agent so that the cells were antiparallel to each other, thereby producing a cell. Thereafter, the cell was heated to 120 ° C., the above-mentioned liquid crystal composition heated to 120 ° C. was injected, and cooled to room temperature at a rate of temperature decrease of 2 ° C./min, to produce a liquid crystal element. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, two types of domains, a bright state and a dark state, were generated even when an electric field was applied. Could not be obtained. In addition, the physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured for one of the domains.

Comparative Example 6 As a comparison, the liquid crystal composition prepared in Comparative Example 2 was added with the formula (1)
7% by weight of the optically active compound represented by 1) was added,
After heating and melting at 0 ° C., the mixture was cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 78 64 53 10 ℃ less then prepared two 1.1mm thick glass plate, on each of the glass plates, to form an ITO film, further Surface treatment was performed. XL-1400 [polyimide (manufactured by Hitachi Chemical Co., Ltd.)] is spin-coated on the glass plate with the ITO film so as to have a thickness of 200 Å as an insulating orientation control layer. The firing was performed for 200 hours, and then the firing was performed at 200 ° C. for 1 hour. After cooling the glass plate to room temperature, this orientation control layer is subjected to a rubbing treatment. Thereafter, silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates, and the rubbing treatment shafts of the two glass plates are separated. Were bonded to each other using a sealing agent so that the cells were antiparallel to each other, thereby producing a cell. Thereafter, the cell was heated to 120 ° C., the above-mentioned liquid crystal composition heated to 120 ° C. was injected, and cooled to room temperature at a rate of temperature decrease of 2 ° C./min, to produce a liquid crystal element. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, two types of domains, a bright state and a dark state, were generated even when an electric field was applied. Could not be obtained. In addition, the physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured for one of the domains.

Comparative Example 7 As a comparison, the liquid crystal composition prepared in Comparative Example 4 was added with the formula (1)
7% by weight of the optically active compound represented by 1) was added,
After heating and melting at 0 ° C., the mixture was cooled to room temperature to prepare a liquid crystal composition (ferroelectric liquid crystal composition). The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 69 65 49 10 ℃ less then prepared two 1.1mm thick glass plate, on each of the glass plates, to form an ITO film, further Surface treatment was performed. XL-1400 [polyimide (manufactured by Hitachi Chemical Co., Ltd.)] is spin-coated on the glass plate with the ITO film so as to have a thickness of 200 Å as an insulating orientation control layer. The firing was performed for 200 hours, and then the firing was performed at 200 ° C. for 1 hour. After cooling the glass plate to room temperature, this orientation control layer is subjected to a rubbing treatment. Thereafter, silica beads having an average particle size of 1.9 μm are sprayed on one of the glass plates, and the rubbing treatment shafts of the two glass plates are separated. Were bonded to each other using a sealing agent so that the cells were antiparallel to each other, thereby producing a cell. Thereafter, the cell was heated to 120 ° C., the above-mentioned liquid crystal composition heated to 120 ° C. was injected, and cooled to room temperature at a rate of temperature decrease of 2 ° C./min, to produce a liquid crystal element. The liquid crystal element was placed in a polarizing microscope in a crossed Nicols state, and the alignment state was observed. As a result, stripe-shaped defects were observed. In addition, physical properties of the liquid crystal composition at room temperature (25 ° C.) were measured and are shown in Table 1.

Example 5 Preparation of Liquid Crystal Composition In Example 3, instead of using the optically active compound represented by the formula (11), an optically active compound represented by the formula (12) A liquid crystal composition (ferroelectric liquid crystal composition) was prepared in accordance with the procedure described in Example 3, except that 7.0 wt% was added to the liquid crystal composition prepared in Example 1. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 88 78 69 10 ℃ below

[0113]

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Example 6: Preparation of liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 5 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, a favorable uniform alignment state was observed. Room temperature (25 ° C)
Table 1 shows the physical properties of the liquid crystal composition.

Example 7: Preparation of liquid crystal composition In Example 3, instead of using the optically active compound represented by the formula (11), an optically active compound represented by the formula (13) A liquid crystal composition (ferroelectric liquid crystal composition) was prepared in accordance with the procedure described in Example 3, except that 7.0 wt% was added to the liquid crystal composition prepared in Example 1. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 88 77 69 10 ℃ below

[0116]

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Example 8: Preparation of a liquid crystal device Example 4 was repeated except that the liquid crystal composition prepared in Example 7 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, a favorable uniform alignment state was observed. Room temperature (25 ° C)
Table 1 shows the physical properties of the liquid crystal composition.

Example 9: Preparation of liquid crystal composition In Example 3, instead of using the optically active compound represented by the formula (11), an optically active compound represented by the formula (14) A liquid crystal composition (ferroelectric liquid crystal composition) was prepared in accordance with the procedure described in Example 3, except that 7.0 wt% was added to the liquid crystal composition prepared in Example 1. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 89 79 68 10 ℃ below

[0119]

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Example 10: Preparation of a liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 9 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed, a favorable uniform alignment state was observed. Room temperature (25 ° C)
Table 1 shows the physical properties of the liquid crystal composition.

Example 11: Preparation of liquid crystal composition In Example 3, instead of using the optically active compound represented by the formula (11), an optically active compound represented by the formula (15) (formula 53) was used. A liquid crystal composition (ferroelectric liquid crystal composition) was prepared in accordance with the procedure described in Example 3, except that 7.0 wt% was added to the liquid crystal composition prepared in Example 1. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 88 74 64 10 ℃ below

[0122]

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Example 12: Preparation of a liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 11 was used instead of the liquid crystal composition prepared in Example 3. A liquid crystal element was manufactured according to the operation described. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 13: Preparation of liquid crystal composition In Example 3, instead of using the optically active compound represented by the formula (11), an optically active compound represented by the formula (16) A liquid crystal composition (ferroelectric liquid crystal composition) was prepared in accordance with the procedure described in Example 3, except that 7.0 wt% was added to the liquid crystal composition prepared in Example 1. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 89 78 62 10 ℃ below

[0125]

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Example 14: Preparation of liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 13 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 15: Preparation of liquid crystal composition To the liquid crystal composition prepared in Example 2, 7.0% by weight of an optically active compound represented by the formula (11) was added, and the mixture was heated and melted at 100 ° C. , cooled to room temperature, the liquid crystal composition (ferroelectric liquid crystal composition was prepared. the phase transition temperatures of this liquid crystal composition (℃) shown _{below. · I → Ch → S a} → S c * → C 90 79 68 10 ° C or less

Example 16: Preparation of liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 15 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 17 Preparation of Liquid Crystal Composition To the liquid crystal composition prepared in Example 2, 7.0% by weight of an optically active compound represented by the formula (12) was added, and the mixture was heated and melted at 100 ° C. , cooled to room temperature, the liquid crystal composition (ferroelectric liquid crystal composition was prepared. the phase transition temperatures of this liquid crystal composition (℃) shown _{below. · I → Ch → S a} → S c * → C 92 86 65 10 ° C or less

Example 18: Preparation of a liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 17 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 19: Preparation of liquid crystal composition The following compound group (Formula 55) was mixed at the following ratio, melted by heating at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. . Further, to this liquid crystal composition, 7.0% by weight of an optically active compound represented by the formula (11) was added, and the mixture was heated and melted at 100 ° C., and then cooled to room temperature. Was prepared. The phase transition temperature (° C.) of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 95 88 72 10 ℃ below

[0132]

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Example 20: Preparation of a liquid crystal device Example 4 was repeated except that the liquid crystal composition prepared in Example 19 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 21: Preparation of liquid crystal composition The following compound group (Formula 56) was mixed at the ratio shown below, heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. . Further, to this liquid crystal composition, 7.0% by weight of an optically active compound represented by the formula (11) was added, and the mixture was heated and melted at 100 ° C., and then cooled to room temperature. Was prepared. The phase transition temperature of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 90 83 64 10 ℃ below

[0135]

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Example 22: Preparation of a liquid crystal element Example 4 was repeated, except that the liquid crystal composition prepared in Example 21 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

Example 23: Preparation of liquid crystal composition The following compound group (Formula 57) was mixed in the ratio shown below, heated and melted at 100 ° C., and then cooled to room temperature to prepare a liquid crystal composition. . Further, to this liquid crystal composition, 7.0% by weight of an optically active compound represented by the formula (11) was added, and the mixture was heated and melted at 100 ° C., and then cooled to room temperature. Was prepared. The phase transition temperature of this liquid crystal composition is shown below. _{· I → Ch → S A →} S c * → C 91 85 71 10 ℃ below

[0138]

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Example 24: Preparation of a liquid crystal element Example 4 was repeated except that the liquid crystal composition prepared in Example 23 was used instead of the liquid crystal composition prepared in Example 3. According to the operation described, a liquid crystal element was manufactured. When this liquid crystal element was placed in a polarizing microscope in a crossed Nicols state and its alignment state was observed,
A good uniform alignment state was observed. In addition, room temperature (25
C), and the physical properties of the liquid crystal composition were measured and are shown in Table 1.

[0140]

[Table 1] As is clear from Table 1, each Example and Comparative Example, it is found that the liquid crystal composition of the present invention has a wide liquid crystal temperature range, has excellent alignment characteristics, and has a stable memory state.

[0141]

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

[Brief description of the drawings]

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

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

[Explanation of symbols]

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

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

Claims (6)

[Claims] 1. A non-optically active naphthylpyrimidine compound represented by at least one of the following general formulas (1) and (2), and a non-optically active naphthylpyrimidine compound represented by at least one of the following general formulas (2) and (2). A liquid crystal composition comprising an optically active phenylpyrimidine compound and at least one non-optically active thiadiazole compound represented by the following general formula (3). Embedded image [Wherein, 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, or 2 to 24 carbon atoms which may be substituted with a halogen atom. And a non-adjacent —CH ₂ — group present in these groups (provided that Y ₁₁ ,
Y ₁₂ or -CH is bonded to an aromatic ring ₂ - group is excluded)
May be replaced by an oxygen atom, a sulfur atom, a —CO— group, a —COO— group or a —OCO— group, and A ₁₁ and A ₁₂ are a substituted or unsubstituted 1,4-phenylene group; A pyridine-2,5-diyl group or a trans-1,4-cyclohexylene group, X ₁₁ and X
₁₂ is a single bond, -COO- group, -OCO- group, -OCH ₂
— Or —CH ₂ O—, wherein Y ₁₁ and Y ₁₂ are —
Represents an O- group, a -COO- group or a -OCO- group,
b, p and q each represent 0 or 1.] [Wherein, R ₂₁ and R ₂₂ each represent a linear or branched alkyl group having 1 to 12 carbon atoms, and Y ₂₁ and Y ₂₂ each represent a single bond or an —O— group]. [Wherein, R ₃₁ and R ₃₂ represent a linear or branched alkyl group having 1 to 12 carbon atoms, and Y ₃₁ and Y ₃₂ represent a single bond or an —O— group] 2. The liquid crystal composition according to claim 1, wherein the non-optically active naphthylpyrimidine compound represented by the general formula (1) is a compound wherein p + q is 0 or 1. 3. The content of at least one non-optically active naphthylpyrimidine compound represented by the general formula (1) is 10
-60% by weight, and the content of at least one non-optically active phenylpyrimidine compound represented by the general formula (2) is 10-60% by weight, and represented by at least one general formula (3). The liquid crystal composition according to claim 1, wherein the content of the non-optically active thiadiazole compound is 10 to 60% by weight. 4. A liquid crystal composition comprising: an isotropic liquid from a high temperature side;
2. A phase series comprising a nematic phase, a smectic A phase, and a smectic C phase.
4. The liquid crystal composition according to any one of items 1 to 3. 5. A liquid crystal composition comprising the liquid crystal composition according to claim 1 and at least one optically active compound. 6. A liquid crystal device comprising the liquid crystal composition according to claim 5 disposed between a pair of electrode substrates.