JPH10130202A - Naphthalene compound, liquid crystal composition and liquid crystal element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound having a wide liquid crystal temperature region and useful for practical use of a ferroelectric liquid crystal element as a constituting component of a liquid crystal composition. SOLUTION: This compound is expressed by the formula Y1 is a single bond or O; Y2 is a single bond, etc.; R1 and R2 are each a (substituted 2-24C alkyl, etc.; X is H or a halogen; (i) is 0 or 1}, e.g. (s)-2-hydroxy-6-(2'- methylbutyloxy)naphthalene. The compound of the formula is obtained by condensing a compound of formula II with a compound of formula III in the presence of a dehydration condensing agent such as N,N'-dicyclohexylcarbodiimide(DCC) and a catalyst (e.g. 4-pyrolidinopyridine). The compound is added to a liquid crystal composition to improve a response time, orientation and a contrast ratio, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel naphthalene compound. More specifically, the present invention relates to a novel naphthalene compound useful as a component of a liquid crystal composition used for a liquid crystal display device, a liquid crystal composition containing the compound, and a liquid crystal device using the liquid crystal composition.

[0002]

2. Description of the Related Art 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 (high-speed response, alignment, high contrast ratio, memory stability, temperature dependence of these characteristics, etc.) required for application to the ferroelectric liquid crystal display device actually used. At present, a single compound cannot be used for optimization, and a ferroelectric liquid crystal composition obtained by mixing several liquid crystal compounds is used. Further, as the ferroelectric liquid crystal composition, not only a ferroelectric liquid crystal composition comprising a compound exhibiting a ferroelectric liquid crystal phase but also a non-chiral smectic C phase is disclosed in JP-A-61-195187. It has been reported that a compound or a composition 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 whole as a ferroelectric liquid crystal composition. Further, a compound or composition showing a phase such as a smectic C phase is used as a basic substance, and one or more compounds which are optically active but do not show a ferroelectric liquid crystal phase are mixed to form a ferroelectric liquid crystal composition as a whole. There are reports (Mol. Cryst. Liq. Cryst., 89, 32)
7 (1982)).

[0004] In summary, irrespective of whether a ferroelectric liquid crystal phase is exhibited or not, one or more optically active compounds are mixed with an achiral compound exhibiting a phase such as a smectic C phase. This shows that a ferroelectric liquid crystal composition can be formed. As described above, various compounds can be used as components of the liquid crystal composition, but in practice, a liquid crystal compound or a mixture exhibiting a smectic C phase or a chiral 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, biphenyl-based liquid crystal compounds, phenylpyrimidine-based liquid crystal compounds, and tolan-based liquid crystal compounds are known. However, it cannot be said that the liquid crystal compositions containing these compounds as constituents still have sufficient properties. Therefore, at present, various tests are conducted on materials exhibiting the smectic C phase or the chiral smectic C phase, and the response time, the memory stability, the layer structure in the smectic C phase, the tilt angle, the alignment characteristics on the alignment film, and the liquid crystal composition In such a case, it is necessary to optimize the compatibility between the liquid crystal compounds.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a ferroelectric liquid crystal device having a wide liquid crystal temperature range and a high speed response when compounded into a ferroelectric liquid crystal composition. It is intended to provide a compound suitable for improving various properties such as alignment, high contrast ratio, etc., a liquid crystal composition containing the compound, and a liquid crystal device using the composition.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above problems, and as a result, have found a certain kind of naphthalene compound, and have reached the present invention. That is,
The present invention relates to a naphthalene compound represented by the general formula (1) (Formula 2). The present invention also relates to a liquid crystal composition containing at least one kind of the naphthalene compound represented by the general formula (1), and a liquid crystal device using the composition.

[0007]

Embedded image [In the formula, Y ₁ represents a single bond or a —O— group; Y ₂ represents a single bond, a —O— group, a —CO— group, a —COO— group, and a —O
Represents a group selected from the group consisting of a CO- group, wherein R ₁ , R ₂
Is a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, or a linear or branched unsaturated group having 2 to 24 carbon atoms which may be substituted with a halogen atom. Alkyl groups, straight-chain or branched-chain alkoxyalkyl groups having 2 to 24 carbon atoms which may be substituted by halogen atoms or straight-chain or branched-chain alkoxyalkyl groups having 3 to 24 carbon atoms which may be substituted by halogen atoms. Represents a saturated alkoxyalkyl group, R ₁ and R ₂ may have an asymmetric carbon, and the asymmetric carbon may be optically active; X represents a hydrogen atom or a halogen atom; Or 1)

[0008]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. In the naphthalene compound represented by the general formula (1) of the present invention, Y ₁ represents a single bond or a —O— group, and Y ₂ represents a single bond, a —O— group, a —CO— group, a —COO— group and −
It represents a group selected from the group consisting of OCO- group, R _1, R
₂ is a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, or a linear or branched alkyl group having 2 to 24 carbon atoms which may be substituted with a halogen atom. A saturated alkyl group, a linear or branched alkoxyalkyl group having 2 to 24 carbon atoms which may be substituted with a halogen atom, or an unsaturated alkoxyalkyl group having 3 to 24 carbon atoms which may be substituted with a halogen atom. Wherein R ₁ and R ₂ may have an asymmetric carbon, which may be optically active, X represents a hydrogen atom or a halogen atom, and i represents 0 or 1.
The naphthalene compound represented by the general formula (1) of the present invention is
Y ₁ is a single bond or —O— group, Y ₂ is a single bond, —O—
When it is a group, -CO- group, -COO- group or -OCO- group, the following (1-A1), (1-A2), (1
-B1), (1-B2), (1-C1), (1-C
2), (1-D1), (1-D2), (1-E1),
(1-E2) It has ten kinds of structures of (Formula 3). Preferred naphthalene compounds are (1-B2), (1-C2) or (1-D2).

[0009]

Embedded image

In the naphthalene compound represented by the general formula (1) of the present invention, R ₁ and R ₂ are each a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom. A straight-chain or branched unsaturated alkyl group having 2 to 24 carbon atoms which may be substituted by a halogen atom, a straight-chain or branched alkoxyalkyl having 2 to 24 carbon atoms which may be substituted by a halogen atom, 3 to 2 carbon atoms which may be substituted with a group or a halogen atom
4 represents an unsaturated alkoxyalkyl group, R ₁ and R
₂ may have an asymmetric carbon, and the asymmetric carbon may be optically active. R ₁ and R ₂ preferably have 4 to 22 carbon atoms, and more preferably 5 to 20 carbon atoms.

Specific examples of the groups represented by R ₁ and R ₂ include, for example, a methyl group, an ethyl group, an n-propyl group,
n-butyl group, n-pentyl group, n-hexyl group, n-
Heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n
-Hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n
-Tetracosyl group, 1-methylethyl group, 1,1-dimethylethyl group, 1-methylpropyl group, 1-ethylpropyl group, 1-n-propylpropyl group, 1-methylbutyl group, 1-ethylbutyl group, 1- n-propylbutyl group, 1-n-butylbutyl group, 1-methylpentyl group,
1-ethylpentyl group, 1-n-propylpentyl group,
1-n-butylpentyl group, 1-n-pentylpentyl group, 1-methylhexyl group, 1-ethylhexyl group, 1
-N-propylhexyl group, 1-n-butylhexyl group, 1-n-pentylhexyl group, 1-n-hexylhexyl group, 1-methylheptyl group, 1-ethylheptyl group, 1-n-propylheptyl group , 1-n-butylheptyl group, 1-n-pentylheptyl group, 1-n-heptylheptyl group, 1-methyloctyl group, 1-ethyloctyl group, 1-n-propyloctyl group, 1-n-butyl Octyl 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-dimethyl Rubuchiru group, 2,3,3-trimethyl butyl group, a 3-methylbutyl group, 3-methylpentyl group, 3-ethylpentyl group, 4-methylpentyl group, 4
-Ethylhexyl group, 2,3-dimethylpentyl group,
2,4-dimethylpentyl group, 2,4,4-trimethylpentyl group, 2,3,3,4-tetramethylpentyl group, 3-methylhexyl group, 2,5-dimethylhexyl group, 3-ethylhexyl group, Alkyl groups such as 3,5,5, -trimethylhexyl group, 4-methylhexyl group, 6-methylheptyl group, 3,7-dimethyloctyl group, 6-methyloctyl group,

2-fluoroethyl group, 1,2-difluoroethyl 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, trifluoromethyl group, perfluoroethyl group, perfluoro-n-propyl group, perfluoro-n-butyl group, perfluoro-n-pentyl Group, perfluoro-
n-hexyl group, perfluoro-n-heptyl group, perfluoro-n-octyl group, perfluoro-n-nonyl group, perfluoro-n-decyl group, perfluoro-n-
Undecyl group, perfluoro-n-dodecyl group, perfluoro-n-tetradecyl group,

1-hydroperfluoroethyl, 1-hydroperfluoro-n-propyl, 1-hydroperfluoro-n-butyl, 1-hydroperfluoro-n-
Pentyl group, 1-hydroperfluoro-n-hexyl group, 1-hydroperfluoro-n-heptyl group, 1-hydroperfluoro-n-octyl group, 1-hydroperfluoro-n-nonyl group, 1-hydro Perfluoro-n-
Decyl group, 1-hydroperfluoro-n-undecyl group, 1-hydroperfluoro-n-dodecyl group, 1-hydroperfluoro-n-tetradecyl group, 1,1-dihydroperfluoroethyl group, 1,1- Dihydroperfluoro-n-propyl group, 1,1-dihydroperfluoro-n-butyl group, 1,1-dihydroperfluoro-n-
Pentyl group, 1,1-dihydroperfluoro-n-hexyl group, 1,1-dihydroperfluoro-n-heptyl group, 1,1-dihydroperfluoro-n-octyl group,
1,1-dihydroperfluoro-n-nonyl group, 1,1
-Dihydroperfluoro-n-decyl group, 1,1-dihydroperfluoro-n-undecyl group, 1,1-dihydroperfluoro-n-dodecyl group, 1,1-dihydroperfluoro-n-tetradecyl group, 1 , 1-Dihydroperfluoro-n-pentadecyl group, 1,1-dihydroperfluoro-n-hexadecyl group, 1,1,2-trihydroperfluoroethyl group, 1,1,3-trihydroperfluoro-n -Propyl group, 1,1,3-trihydroperfluoro-n-butyl group, 1,1,4-trihydroperfluoro-n-butyl group, 1,1,4-trihydroperfluoro-n-pentyl Group, 1,1,5-trihydroperfluoro-n-pentyl group, 1,1,3-trihydroperfluoro-n-hexyl group, 1,1,6-trihydroperfluoro -n- hexyl group, 1,1,5-tri hydro perfluoro -n- heptyl, 1,1,7-
Trihydroperfluoro-n-heptyl group, 1,1,8
-Trihydroperfluoro-n-octyl group, 1,1,
9-trihydroperfluoro-n-nonyl group, 1,1,
11-trihydroperfluoro-n-undecyl group,

2- (perfluoroethyl) ethyl group, 2
-(Perfluoro-n-propyl) ethyl group, 2- (perfluoro-n-butyl) ethyl group, 2- (perfluoro-n-pentyl) ethyl group, 2- (perfluoro-n
-Hexyl) ethyl group, 2- (perfluoro-n-heptyl) ethyl group, 2- (perfluoro-n-octyl)
Ethyl group, 2- (perfluoro-n-decyl) ethyl group, 2- (perfluoro-n-nonyl) ethyl group, 2-
(Perfluoro-n-dodecyl) ethyl group, 2-trifluoromethylpropyl group, 3- (perfluoro-n-propyl) propyl group, 3- (perfluoro-n-butyl) propyl group, 3- (perfluoro -N-hexyl)
Propyl group, 3- (perfluoro-n-heptyl) propyl group, 3- (perfluoro-n-octyl) propyl group, 3- (perfluoro-n-decyl) propyl group, 3
-(Perfluoro-n-dodecyl) propyl group, 4-
(Perfluoroethyl) butyl group, 4- (perfluoro-n-propyl) butyl group, 4- (perfluoro-n-
Butyl) butyl group, 4- (perfluoro-n-pentyl) butyl group, 4- (perfluoro-n-hexyl) butyl group, 4- (perfluoro-n-heptyl) butyl group, 4- (perfluoro- n-octyl) butyl group, 4
-(Perfluoro-n-decyl) butyl group, 5- (perfluoro-n-propyl) pentyl group, 5- (perfluoro-n-butyl) pentyl group, 5- (perfluoro-
n-pentyl) pentyl group, 5- (perfluoro-n-
Hexyl) pentyl group, 5- (perfluoro-n-heptyl) pentyl group, 5- (perfluoro-n-octyl) pentyl group, 6- (perfluoroethyl) hexyl group, 6- (perfluoro-n-propyl) ) Hexyl group,
6- (perfluoro-n-butyl) hexyl group, 6-
(Perfluoro-n-hexyl) hexyl group, 6- (perfluoro-n-heptyl) hexyl group, 6- (perfluoro-n-octyl) hexyl group, 7- (perfluoroethyl) heptyl group, 7- ( Perfluoro-n-propyl) heptyl group, 7- (perfluoro-n-butyl)
An alkyl group substituted with a halogen atom such as a heptyl group, a 7- (perfluoro-n-pentyl) heptyl group,

A methoxymethyl group, a 2-methoxyethyl group, a 3-methoxypropyl group, a 4-methoxybutyl group,
5-methoxypentyl group, 6-methoxyhexyl group, 7
-Methoxyheptyl group, 8-methoxyoctyl group, 9-
Methoxynonyl group, 10-methoxydecyl group, ethoxymethyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 5-ethoxypentyl group, 6-ethoxyhexyl group, 7-ethoxyheptyl group, 8-ethoxyoctyl group, 9-ethoxynonyl group,
10-ethoxydecyl group, n-propyloxymethyl group, 2-n-propyloxyethyl group, 3-n-propyloxypropyl group, 4-n-propyloxybutyl group, 5-n-propyloxypentyl group, 6 -N-propyloxyhexyl group, 7-n-propyloxyheptyl group, 8-n-propyloxyoctyl group, 9-n-propyloxynonyl group, 10-n-propyloxydecyl group, n-butyloxymethyl group , 2-n-butyloxyethyl group, 3-n-butyloxypropyl group, 4-n
-Butyloxybutyl group, 5-n-butyloxypentyl group, 6-n-butyloxyhexyl group, 7-n-butyloxyheptyl group, 8-n-butyloxyoctyl group, 9-n-butyloxynonyl group , 10-n-butyloxydecyl group, n-pentyloxymethyl group, 2-n
-Pentyloxyethyl group, 3-n-pentyloxypropyl group, 4-n-pentyloxybutyl group, 5-n-
Pentyloxypentyl group, 6-n-pentyloxyhexyl group, 7-n-pentyloxyheptyl group, 8-n
-Pentyloxyoctyl group, 9-n-pentyloxynonyl group, 10-n-pentyloxydecyl group,

N-hexyloxymethyl group, 2-n-hexyloxyethyl group, 3-n-hexyloxypropyl group, 4-n-hexyloxybutyl group, 5-n-hexyloxypentyl group, 6-n- Hexyloxyhexyl group, 7-n-hexyloxyheptyl group, 8-n-hexyloxyoctyl group, 9-n-hexyloxynonyl group, 10-n-hexyloxydecyl group, n-heptyloxymethyl group, 2- n-heptyloxyethyl group,
3-n-heptyloxypropyl group, 4-n-heptyloxybutyl group, 5-n-heptyloxypentyl group,
6-n-heptyloxyhexyl group, 7-n-heptyloxyheptyl group, 8-n-heptyloxyoctyl group, 9-n-heptyloxynonyl group, 10-n-heptyloxydecyl group, octyloxymethyl group, 2-n
-Octyloxyethyl group, 3-n-octyloxypropyl group, 4-n-octyloxybutyl group, 5-n-
Octyloxypentyl group, 6-n-octyloxyhexyl group, 7-n-octyloxyheptyl group, 8-n
-Octyloxyoctyl group, 9-n-octyloxynonyl group, 10-n-octyloxydecyl group, n-nonyloxymethyl group, 2-n-nonyloxyethyl group,
3-n-nonyloxypropyl group, 4-n-nonyloxybutyl group, 5-n-nonyloxypentyl group, 6-n
-Nonyloxyhexyl group, 7-n-nonyloxyheptyl group, 8-n-nonyloxyoctyl group, 9-n-nonyloxynonyl group, 10-n-nonyloxydecyl group,

N-decyloxymethyl group, 2-n-decyloxyethyl group, 3-n-decyloxypropyl group,
4-n-decyloxybutyl group, 5-n-decyloxypentyl group, 6-n-decyloxyhexyl group, 7-n
-Decyloxyheptyl group, 8-n-decyloxyoctyl group, 9-n-decyloxynonyl group, 10-n-decyloxydecyl group, 2-n-undecyloxyethyl group, 4-n-undecyloxy Butyl group, 6-n-undecyloxyhexyl group, 8-n-undecyloxyoctyl group, 10-n-undecyloxydecyl group, 2-
n-dodecyloxyethyl group, 4-n-dodecyloxybutyl group, 6-n-dodecyloxyhexyl group, 8-n
-Dodecyloxyoctyl group, 10-n-dodecyloxydecyl group, 1-methyl-2-methoxyethyl group, 1-
Methyl-2-ethoxyethyl group, 1-methyl-2-n-
Propyloxyethyl group, 1-methyl-2-n-butyloxyethyl group, 1-methyl-2-n-pentyloxyethyl group, 1-methyl-2-n-hexyloxyethyl group, 1-methyl-2- n-heptyloxyethyl group, 1
-Methyl-2-n-octyloxyethyl group, 1-methyl-2-n-nonyloxyethyl group, 1-methyl-2-
n-decyloxyethyl group, 1-methyl-2-n-undecyloxyethyl group, 1-methyl-2-n-dodecyloxyethyl group, 2-methoxypropyl group, 2-2-ethoxypropyl group, 2- n-propyloxypropyl group, 2-n-butyloxypropyl group, 2-n-pentyloxypropyl group, 2-n-hexyloxypropyl group, 2-n-heptyloxypropyl group, 2-n-octyloxypropyl Group, 2-n-nonyloxypropyl group, 2-n-decyloxypropyl group, 2-n-undecyloxypropyl group, 2-n-dodecyloxypropyl group,

1-methyl-3-methoxypropyl group, 1
-Methyl-3-ethoxypropyl group, 1-methyl-3-
n-propyloxypropyl group, 1-methyl-3-n-
Butyloxypropyl group, 1-methyl-3-n-pentyloxypropyl group, 1-methyl-3-n-hexyloxypropyl group, 1-methyl-3-n-heptyloxypropyl group, 1-methyl-3- n-octyloxypropyl group, 1-methyl-3-n-nonyloxypropyl group, 1-methyl-3-n-decyloxypropyl group, 1
-Methyl-3-n-undecyloxypropyl group, 1-
Methyl-3-n-dodecyloxypropyl group, 3-methoxybutyl group, 3-ethoxybutyl group, 3-n-propyloxybutyl group, 3-n-butyloxybutyl group, 3
-N-pentyloxybutyl group, 3-n-hexyloxybutyl group, 3-n-heptyloxybutyl group, 3-n
-Octyloxybutyl group, 3-n-nonyloxybutyl group, 3-n-decyloxybutyl group, 3-n-undecyloxybutyl group, 3-n-dodecyloxybutyl group, isopropyloxymethyl group, 2- Isopropyloxyethyl group, 3-isopropyloxypropyl group, 4
-Isopropyloxybutyl group, 5-isopropyloxypentyl group, 6-isopropyloxyhexyl group, 7
-Isopropyloxyheptyl group, 8-isopropyloxyoctyl group, 9-isopropyloxynonyl group, 1
0-isopropyloxydecyl group, isobutyloxymethyl group, 2-isobutyloxyethyl group, 3-isobutyloxypropyl group, 4-isobutyloxybutyl group,
5-isobutyloxypentyl group, 6-isobutyloxyhexyl group, 7-isobutyloxyheptyl group, 8-
Isobutyloxyoctyl group, 9-isobutyloxynonyl group, 10-isobutyloxydecyl group, tert-butyloxymethyl group, 2-tert-butyloxyethyl group,
3-tert-butyloxypropyl group, 4-tert-butyloxybutyl group, 5-tert-butyloxypentyl group,
6-tert-butyloxyhexyl group, 7-tert-butyloxyheptyl group, 8-tert-butyloxyoctyl group, 9-tert-butyloxynonyl group, 10-tert-butyloxydecyl group,

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

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

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

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

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

A (2-ethylhexyloxy) methyl group,
(3,5,5-trimethylhexyloxy) methyl group,
(3,7-dimethyloctyloxy) methyl group, 2-
(2′-ethylhexyloxy) ethyl group, 2-
(3 ′, 5 ′, 5′-trimethylhexyloxy) ethyl group, 2- (3 ′, 7′-dimethyloctyloxy) ethyl group, 3- (2′-ethylhexyloxy) propyl group, 3- (3 ′ , 5 ', 5'-trimethylhexyloxy) propyl group, 3- (3', 7'-dimethyloctyloxy) propyl group, 4- (2'-ethylhexyloxy) butyl group, 4- (3 ', 5' , 5'-trimethylhexyloxy) butyl group, 4- (3 ', 7'-dimethyloctyloxy) butyl group, 5- (2'-ethylhexyloxy) pentyl group, 5- (3', 5 ', 5' -Trimethylhexyloxy) pentyl group, 5- (3 ', 7'
-Dimethyloctyloxy) pentyl group, 6- (2'-
Ethylhexyloxy) hexyl group, 6- (3 ′,
5 ′, 5′-trimethylhexyloxy) hexyl group,
An alkoxyalkyl group such as a 6- (3 ′, 7′-dimethyloctyloxy) hexyl group,

2-propenyloxymethyl group, 2-
(2′-propenyloxy) ethyl group, 2- [2′-
(2 "-propenyloxy) ethoxy] ethyl group, 3-
(2′-propenyloxy) propyl group, 4- (2′-
Propenyloxy) butyl group, 5- (2′-propenyloxy) pentyl group, 6- (2′-propenyloxy)
Hexyl group, 7- (2′-propenyloxy) heptyl group, 8- (2′-propenyloxy) octyl group, 9-
(2′-propenyloxy) nonyl group, 10- (2′-
Unsaturated alkoxyalkyl groups such as propenyloxy) decyl group,

2- (2'-trifluoromethylpropyloxy) ethyl, 4- (2'-trifluoromethylpropyloxy) butyl, 6- (2'-trifluoromethylpropyloxy) hexyl, 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,

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 ′,
An alkoxyalkyl group substituted with a halogen atom such as 3′-dichloro-n-butyloxy) octyl group,

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

When R ₁ and R ₂ have an asymmetric carbon,
The asymmetric carbon may be optically active or non-optically active. When the asymmetric carbon is optically active, its absolute configuration may be S configuration or R configuration. When the asymmetric carbon is optically active, the optical purity is any purity in the range of 2 to 100% ee, and preferably 50 to 100% ee. Also, R
_The case where both ₁ and R ₂ are groups having an optically active asymmetric carbon is also included in the present invention. In this case, the absolute configurations of the optically active groups of R ₁ and R ₂ may be the same absolute configuration, or may be the opposite absolute configurations. In the naphthalene compound represented by the general formula (1) of the present invention, Y ₁ represents a single bond or an —O— group;
₂ represents a single bond, -O- group, -CO- group, -COO- group and a connecting group selected from the group consisting of -OCO- group,
Preferably, it represents a -O- group, a -CO- group or a -COO- group. X represents a hydrogen atom or a halogen atom, and preferably represents a hydrogen atom, a fluorine atom or a chlorine atom.
i represents 0 or 1. Specific examples of the naphthalene compound represented by the general formula (1) of the present invention include the following (Table 1)
To (Table 16). Note that “↑” in the table represents “same as above”.

[0031]

[Table 1]

[0032]

[Table 2]

[0033]

[Table 3]

[0034]

[Table 4]

[0035]

[Table 5]

[0036]

[Table 6]

[0037]

[Table 7]

[0038]

[Table 8]

[0039]

[Table 9]

[0040]

[Table 10]

[0041]

[Table 11]

[0042]

[Table 12]

[0043]

[Table 13]

[0044]

[Table 14]

[0045]

[Table 15]

[0046]

[Table 16] The naphthalene compound represented by the general formula (1) of the present invention is
For example, it can be produced through the following step (Formula 4).

[0047]

Embedded image That is, a compound represented by the general formula (2) and a cinnamic acid derivative represented by the general formula (3) are combined with a dehydration condensing agent such as N, N'-dicyclohexylcarbodiimide (hereinafter abbreviated as DCC) and a catalyst ( For example, it can be produced by condensation in the presence of 4-N, N-dimethylaminopyridine, 4-pyrrolidinopyridine). In addition, the compound represented by the general formula (2) can be produced according to the following method depending on the type of Y ₂ . In the case of a compound in which Y ₂ is a single bond, the compound can be produced, for example, through the following step (Formula 5).

[0048]

Embedded image That is, a carboxylic acid chloride is allowed to act on a compound represented by the formula (4) in the presence of aluminum chloride to introduce an acyl group by a Friedel-Crafts reaction, and then, an acylated product represented by the general formula (5) Or a method of reacting a compound represented by the general formula (6) with an acetylene compound in the presence of a palladium catalyst to form an acetylene derivative, followed by reduction and removal of a protecting group. it can. In the case of a compound in which Y ₂ is an —O— group, the compound can be produced, for example, through the following step (Formula 6).

[0049]

Embedded image That is, a method in which an alkylating agent is allowed to act on the dihydroxy compound represented by the formula (7) in the presence of a base, or an alcohol and diethyl are reacted with the dihydroxy compound represented by the formula (7) in the presence of triphenylphosphine. It can be obtained by a method of reacting azodicarboxylic acid (hereinafter abbreviated as DEAD). In the case of a compound in which Y ₂ is a —CO— group, the compound can be produced, for example, through the following step (Formula 7).

[0050]

Embedded image That is, a method in which carboxylic acid chloride is allowed to act on the compound represented by the formula (4) in the presence of aluminum chloride, or a compound represented by the general formula (8) is acted on by a Grignard reagent, hydrolyzed, and protected. It can be obtained by a method of removing a group. In the case where the compound in which Y ₂ is a —COO— group, for example,
It can be produced through the following step (Chem. 8).

[0051]

Embedded image That is, a method of reacting a carboxylic acid derivative represented by the general formula (9) with a chlorinating agent such as oxalyl chloride to form an acid chloride, followed by an alcohol to remove a protecting group, and a method of the general formula (9) In the presence of triphenylphosphine, an alcohol and D
A method of reacting EAD and then removing the protecting group, or in the presence of a base such as potassium carbonate in a hydroxynaphthalenecarboxylic acid represented by the formula (10) in a polar solvent such as N, N-dimethylformamide. It can be obtained by a method of reacting an alkylating agent. In the case where the compound in which Y ₂ is an —OCO— group, for example,
It can be produced through the following step (Chem. 9).

[0052]

Embedded image That is, it can be obtained by a method in which carboxylic acid chloride is allowed to act on the dihydroxy compound represented by the formula (7) in the presence of a base. The cinnamic acid derivative represented by the general formula (3) can be produced, for example, according to the following method (Chem. 10).

[0053]

Embedded image

That is, when Y ₁ is an —O— group in the general formula (3), a cinnamic acid derivative represented by the general formula (11) is added to a base (eg, sodium hydroxide, potassium hydroxide). It can be produced by allowing an alkylating agent such as an alkyl bromide to act in the presence. Further, a method in which acetic anhydride is allowed to act on an aldehyde represented by the general formula (12) in the presence of a base (eg, potassium acetate or sodium acetate); A method of reacting malonic acid in the presence of sodium hydroxide, potassium hydroxide) in the presence of a base (eg, sodium hydroxide, potassium hydroxide, potassium-tert-butoxide) on an aldehyde represented by the general formula (12) , (Alkoxycarbonylmethyl) triphenylphosphonium halide, and then hydrolyzing the resulting cinnamic acid ester derivative.

The naphthalene compound of the present invention includes a compound which exhibits liquid crystallinity by itself and a compound which does not exhibit liquid crystallinity. Compounds exhibiting liquid crystallinity include smectic C
Phase (hereinafter abbreviated as S _C phase) or chiral smectic C phase (hereinafter abbreviated as S _C ^* phase) and a compound exhibiting liquid crystallinity but exhibiting no S _C phase or S _C ^* phase There is. Each of these compounds can be effectively used as a component of a liquid crystal composition.

Next, the liquid crystal composition of the present invention will be described. Generally, the liquid crystal composition is composed of two or more components. The liquid crystal composition of the present invention contains at least one naphthalene compound of the present invention as an essential component. The naphthalene compound of the present invention used in the liquid crystal composition of the present invention includes a naphthalene compound having no liquid crystallinity, S
Naphthalene compound showing _C phase, naphthalene compound showing S _C ^* phase, and S _C phase and S _C ^* showing liquid crystallinity
Naphthalene compounds that do not show a phase are mentioned. The liquid crystal composition of the present invention preferably includes a liquid crystal composition exhibiting a phase such as chiral smectic C, F, G, H, or I, and more preferably a liquid crystal composition exhibiting an S _C ^* phase. .

The liquid crystal composition exhibiting the S _C ^* phase of the present invention exhibits the naphthalene compound of the present invention, the liquid crystal compound exhibiting an S _C ^* phase other than the naphthalene compound of the present invention, and the Sc phase other than the naphthalene compound of the present invention. It is a composition prepared by combining a plurality of compounds selected from a liquid crystal compound and an optically active compound, and contains at least one naphthalene compound of the present invention. The liquid crystal compound exhibiting an S _C ^* phase other than the naphthalene compound of the present invention is not particularly limited. For example, an optically active phenylbenzoate liquid crystal compound, an optically active biphenylbenzoate liquid crystal compound, an optically active naphthalene liquid crystal Compound, optically active phenylnaphthalene-based liquid crystal compound, optically active tolan-based liquid crystal compound, optically active phenylpyrimidine-based liquid crystal compound,
An optically active naphthylpyrimidine-based liquid crystal compound can be mentioned.

The liquid crystal compound exhibiting an S _C phase other than the naphthalene compound of the present invention is not particularly limited. Liquid crystal compounds, tolan liquid crystal compounds, phenylpyrimidine liquid crystal compounds, and naphthylpyrimidine liquid crystal compounds. The optically active compound does not exhibit liquid crystallinity by itself,
By mixing a liquid crystal composition showing a liquid crystal compound or S _C phase shows a S _C phase, denotes a compound capable of expressing the S _C ^* phase. The optically active compound is not particularly limited. For example, an optically active phenylbenzoate-based non-liquid crystal compound, an optically active biphenylbenzoate-based non-liquid crystal compound, an optically active naphthalene-based non-liquid crystal compound, an optically active phenylnaphthalene-based non-liquid crystal Compounds, optically active phenylpyrimidine-based non-liquid crystal compounds, optically active naphthylpyrimidine-based non-liquid crystal compounds, and optically active tolan-based non-liquid crystal compounds can be exemplified.

[0059] Further, the liquid crystal composition of the present invention, in addition to the above essential components, smectic and nematic liquid crystal compound do not exhibit S _C phase as an optional component, no liquid crystallinity other than the naphthalene compounds of the present invention compounds (For example, a dichroic dye such as an anthraquinone dye or an azo dye, and a conductivity-imparting agent or a life-improving agent). In the liquid crystal composition of the present invention, the content of the naphthalene compound of the present invention is not particularly limited, but is usually 5 to 99% by weight, preferably 10 to 90% by weight. In the liquid crystal composition of the present invention, the liquid crystal composition exhibiting chiral smectic C, F, G, H, and I phases is a liquid crystal composition exhibiting ferroelectricity. A liquid crystal composition exhibiting ferroelectricity causes a switching phenomenon when a voltage is applied, and a liquid crystal display device having a short response time can be manufactured using the switching phenomenon. The naphthalene compound of the present invention comprises at least one
The liquid crystal composition containing species, the response time as compared with the liquid crystal composition conventionally known, memory stability, layer structure, the tilt angle in the S _C phase, orientation characteristics and liquid crystal compound in the alignment film Excellent in compatibility between them.

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

The insulating alignment control layer 4 is for rubbing a thin film of a polymer such as polyimide with a flocked cloth such as nylon, acetate, rayon or the like to align the liquid crystal. Examples of the material of the insulating orientation control layer 4 include silicon nitride, silicon nitride containing hydrogen, silicon carbide, silicon carbide containing hydrogen, silicon oxide, boron nitride, and boron nitride containing hydrogen. , Cerium oxide, aluminum oxide, zirconium oxide, inorganic insulating layers such as titanium oxide and magnesium fluoride, polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyetherimide, polyetherketone, polyetheretherketone, Organic insulating layers such as polyethersulfone, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin, urea resin, and acrylic resin. It is may be an insulating alignment control layer of two-layer structure to form an organic insulating layer on the inorganic insulating layer may be made of only an inorganic insulating layer or an organic insulating layer insulating alignment control layer. 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 penetrating coating method, a screen printing method, a spray coating method, a roll coating method, or the like, under a predetermined condition. The solvent can be removed under (e.g., under heating), and calcined as required. When forming the organic insulating layer, if necessary,
-(3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidyloxypropyltrimethoxysilane, γ-glycidyloxypropylmethyldiethoxysilane, γ-glycidyloxypropyltriethoxysilane, γ-methacryloxypropylmethyldimethoxysilane Γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-methacryloxypropyltriethoxysilane, N-β- (aminoethyl) -γ-aminopropylmethyldimethoxysilane, N-β- (Aminoethyl) -γ-aminopropyltrimethoxysilane, N-β
-(Aminoethyl) -γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-
Surface treatment may be performed using a silane coupling agent such as aminopropyltriethoxysilane or the like, and then an organic insulating layer material or a precursor thereof may be applied. The thickness of the insulating orientation control layer 4 is usually from 10 Å to 1 Å.
μm, preferably 10-3000 Å,
More preferably, it is 10 to 1000 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 sandwiched between the substrates 2 as spacers, and the periphery of the two substrates 2 is sealed with a sealant (for example, an epoxy-based adhesive) so as to have an arbitrary interval. Can be kept. Further, a polymer film or glass fiber may be used as the spacer. A liquid crystal exhibiting a chiral smectic phase is sealed between the two substrates. The thickness of the liquid crystal layer 1 is generally set to 0.5 to 20 μm, preferably 1 to 5 μm, and more preferably 1 to 3 μm. The transparent electrode 3 is connected to an external power supply 7 by a lead wire. Outside the substrate 2, a pair of polarizing plates 8 whose polarization axes are in, for example, a crossed Nicols state are arranged. The example in FIG. 1 is a transmission type,
A light source 9 is provided. Note that 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,
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 naphthalene compound of the present invention and a liquid crystal composition containing the compound may be used in a field other than a liquid crystal element for display (for example, a nonlinear optical function element, an electronic material such as a capacitor material, a limiter, a memory, an amplifier, and a modulator). It can be applied to electronic elements such as, for example, conversion elements for heat, light, pressure, mechanical deformation and the like and voltage conversion elements and sensors, and power generation elements such as thermoelectric power generation elements.

[0064]

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples. The symbols I, Ch, and S in each of the examples and the tables were used.
_A , S _C , S _C ^* and C represent the following meanings. I: Isotropic liquid Ch: Cholesteric phase S _A : Smectic A phase S _C : Smectic C phase S _C ^* : Chiral smectic C phase C: Crystal phase

Production Example 1 (S) -2-hydroxy-6-
Production of (2′-methylbutyloxy) naphthalene A mixture of 16.0 g of 2,6-dihydroxynaphthalene, 13.3 g of anhydrous sodium carbonate and 150 g of N, N-dimethylformamide was heated to 65 ° C., and while stirring, 2) 25.8 g of p-toluenesulfonic acid ester of 2-methylbutanol was added dropwise over 1 hour.
After the dropwise addition, the mixture was further stirred at 65 ° C. for 5 hours, and then the reaction mixture was cooled to room temperature.
Of water, acidified with hydrochloric acid, and extracted with toluene. The toluene was distilled off under reduced pressure, and the target product was separated by silica gel column chromatography, and (S) -2-hydroxy 6- (2′-methylbutyloxy) naphthalene 9.2 was obtained.
g was obtained.

Production Example 2: Production of 2-hydroxy-6-n-heptanoylnaphthalene 2.44 g of magnesium metal and 50 of tetrahydrofuran
To a Grignard reagent prepared from the resulting mixture and 16.9 g of 1-bromohexane, a solution of 25.0 g of 2-tetrahydropyranyloxy-6-cyanonaphthalene in tetrahydrofuran was added dropwise over 1 hour. Thereafter, the mixture was stirred at room temperature for 16 hours, and after filtering off insolubles from the reaction mixture, tetrahydrofuran was distilled off and 200 ml of toluene was added. To this toluene solution, 150 ml of 10% by weight hydrochloric acid was added, and the mixture was heated and stirred at 50 ° C. for 3 hours. Thereafter, the toluene phase was separated, washed with water, and toluene was distilled off to remove 2-hydroxy-6-n-heptylcarbonylnaphthalene.
9 g were obtained.

Production Example 3: Production of 2-hydroxy-6-n-decyloxycarbonylnaphthalene 18.8 g (0.1 mol) of 2-hydroxy-6-naphthoic acid, 150 g of N, N-dimethylformamide and anhydrous sodium carbonate 13.3 g (0.125 mol) of the mixture was heated to 70 ° C., and 26.5 g (0.12 mol) of n-decyl bromide was added dropwise with stirring over 1 hour while stirring. After the dropwise addition, the mixture was further stirred at 70 ° C. for 6 hours. Thereafter, the reaction mixture was cooled to room temperature, and after filtering the inorganic salt, the filtrate was discharged into 1000 g of water. The precipitated solid was separated, washed with n-hexane, dried, and dried to obtain 30.2 g.
Of 2-hydroxy-6-n-decyloxycarbonylnaphthalene was obtained.

Production Example 4: (S) -2-hydroxy-6-
Production of (4′-methylhexyloxycarbonyl) naphthalene One drop of N, N-dimethylformamide was added to a mixture of 59.77 g of 2-benzyloxynaphthoic acid, 15.5 g of oxalyl chloride and 470 ml of toluene, and the mixture was added at 75 ° C. For 4 hours. Thereafter, excess oxalyl chloride and toluene were distilled off under reduced pressure,
420 ml of toluene and (S) -4-methyl-
25 g of 1-hexanol was added, the mixture was cooled with ice, and 22.8 g of triethylamine was added dropwise over 1 hour. Thereafter, the mixture was stirred at room temperature for 12 hours, and insolubles were removed by filtration. The filtrate was neutralized with hydrochloric acid, washed with water, and toluene was distilled off. The residue was recrystallized from isopropanol to give 72.5 g of (S) -2.
-Benzyloxy-6- (4'-methylhexyloxycarbonyl) naphthalene was obtained as colorless crystals. Next, 55 g of (S) -2-benzyloxy-6- (4′-methylhexyloxycarbonyl) naphthalene was dissolved in 350 ml of ethyl acetate, and Pd / C (containing 50% by weight of water) was dissolved.
5.5 g was added and the mixture was stirred under a hydrogen atmosphere for 12 hours.
afterwards. Pd / C was filtered off, and ethyl acetate was distilled off from the filtrate to obtain 35 g of (S) -2-hydroxy-6- (4′-methylhexyloxycarbonyl) naphthalene.

Production Example 5: (S) -2-hydroxy-6
Production of (2′-methylbutyloxycarbonyl) naphthalene In Production Example 4, except that (S) -2-methyl-1-butanol was used instead of using (S) -4-methyl-1-hexanol. According to the procedure described in Production Example 4, 30 g of (S) -2-hydroxy-6- (2′-methylbutyloxycarbonyl) naphthalene was obtained.

Production Example 6: 2-hydroxy-6- [2'-
Production of (perfluoro-n-butyl) ethoxycarbonyl] naphthalene In Production Example 4, instead of using (S) -4-methyl-1-hexanol, 2- (perfluoro-n-butyl) ethanol was used. Other than that, according to the procedure described in Production Example 4, 2-hydroxy-6- [2 ′-(perfluoro-n-butyl) ethoxycarbonyl] naphthalene 4
7 g were obtained.

Production Example 6: 2-hydroxy-6- (2'-
Production of n-hexyloxyethoxycarbonyl) naphthalene In Production Example 4, instead of using (S) -4-methyl-1-hexanol, ethylene glycol mono-n
By following the procedure described in Production Example 4 except for using -hexyl ether, 36 g of 2-hydroxy-6- (2'-n-hexyloxyethoxycarbonyl) naphthalene was obtained.

Production Example 7: 2-hydroxy-6- (2′-
Production of n-butyloxyethoxycarbonyl) naphthalene In Production Example 4, instead of using (S) -4-methyl-1-hexanol, ethylene glycol mono-n
According to the procedure described in Production Example 4 except that -butyl ether was used, 33 g of 2-hydroxy-6- (2'-n-butyloxyethoxycarbonyl) naphthalene was obtained.

Production Example 8 2-Hydroxy-6- [2'-
Production of (2 "-n-hexyloxyethoxy) ethoxycarbonyl] naphthalene In Production Example 4, instead of using (S) -4-methyl-1-hexanol, diethylene glycol mono-
According to the procedure described in Production Example 4 except that n-hexyl ether was used, 2-hydroxy-6- [2 ′-(2 ″) was used.
-N-hexyloxyethoxy) ethoxycarbonyl]
42 g of naphthalene were obtained.

Production Example 9: Production of trans-4-n-decyloxycinnamic acid 6.6 g of trans-4-hydroxycinnamic acid, 5.27 g of potassium hydroxide (85% by weight), and 2.7 of potassium iodide
g and 100 g of water were added to 13.3 g of n-decyl bromide, and the mixture was heated and stirred at 78 ° C. for 24 hours. Thereafter, 12 g of potassium hydroxide and 120 g of water were added, and the mixture was heated and stirred at 80 ° C. for 2 hours. After the reaction solution was cooled to room temperature, it was discharged into cold water (200 ml), hydrochloric acid was added to adjust the pH to 1, and the generated crystals were filtered. The obtained crystals were washed with hexane to obtain 10.2 g of trans-4-n-decyloxycinnamic acid.

Example 1 Preparation of Exemplified Compound 60 Trans-4-n-decyloxycinnamic acid 304 mg,
230 mg of (S) -2-hydroxy-6- (2′-methylbutyloxy) naphthalene and 206 mg of DCC are dissolved in 5 ml of chloroform, 20 mg of 4-pyrrolidinopyridine is added under ice-cooling, and the mixture is stirred at room temperature for 12 hours. Was done. Thereafter, insolubles were filtered off from the reaction mixture, chloroform was distilled off from the filtrate, and the residue was subjected to silica gel chromatography [eluent: chloroform / hexane = 2/1.
(vol / vol)], and the obtained solid was recrystallized twice from methanol-ethyl acetate to obtain 422 mg of Exemplified Compound 60 as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 2: Preparation of Exemplified Compound 114 In Example 1, (S) -2-hydroxy-6- (2 '
Instead of using -methylbutyloxy) naphthalene, 2-hydroxy-6-heptanoylnaphthalene 25
Except for using 6 mg, 403 mg of Exemplified Compound 114 was obtained as colorless crystals according to the procedure described in Example 1.
The phase transition temperature (° C.) of this compound is shown below.

Example 3 Preparation of Exemplified Compound 151 In Example 1, (S) -2-hydroxy-6- (2 ′)
Exemplified compound 151 was obtained as colorless crystals according to the procedure described in Example 1, except that 328 mg of 2-hydroxy-6-n-decyloxycarbonylnaphthalene was used instead of using -methylbutyloxy) naphthalene.
29 mg were obtained. The phase transition temperature (° C.) of this compound is shown below.

Example 4: Preparation of Exemplified Compound 156 In Example 1, (S) -2-hydroxy-6- (2 '
Exemplified compound 156 according to the procedure described in Example 1 except that (S) -2-hydroxy-6- (2'-methylbutyloxycarbonyl) naphthalene was used in an amount of 258 mg instead of using -methylbutyloxy) naphthalene.
Was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 5: Preparation of Exemplified Compound 175 In Example 1, (S) -2-hydroxy-6- (2 '
Instead of using -methylbutyloxy) naphthalene, 2-hydroxy-6- [2 ′-(perfluoro-n
-Butyl) ethoxycarbonyl] naphthalene 434 mg
489 mg of Exemplified Compound 175 as colorless crystals was obtained according to the procedure described in Example 1 except that was used. The phase transition temperature (° C.) of this compound is shown below.

Example 6 Preparation of Exemplified Compound 176 In Example 1, (S) -2-hydroxy-6- (2 ′)
Exemplified compound 17 according to the procedure described in Example 1 except that 286 mg of (S) -2-hydroxy-6- (4'-methylhexyloxycarbonyl) naphthalene was used instead of using -methylbutyloxy) naphthalene.
395 mg of 6 were obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 7: Preparation of Exemplified Compound 178 In Example 1, (S) -2-hydroxy-6- (2 '
Example compound 178 was converted to colorless according to the procedure described in Example 1, except that 284 mg of 2-hydroxy-6- (2'-n-butyloxyethoxycarbonyl) naphthalene was used instead of using -methylbutyloxy) naphthalene. 349 mg were obtained as crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 8: Preparation of Exemplified Compound 181 In Example 1, (S) -2-hydroxy-6- (2 '
Exemplified compound 181 according to the procedure described in Example 1, except that instead of using -methylbutyloxy) naphthalene, 312 mg of 2-hydroxy-6- (2'-n-hexyloxyethoxycarbonyl) naphthalene was used.
Was obtained as colorless crystals. The phase transition temperature (° C.) of this compound is shown below.

Example 9: Preparation of Exemplified Compound 182 In Example 1, (S) -2-hydroxy-6- (2 '
Instead of using -methylbutyloxy) naphthalene, 2-hydroxy-6- [2 '-(2 "-n-hexyloxyethoxy) ethoxycarbonyl] naphthalene 3
Except that 60 mg was used, 398 mg of Exemplified Compound 182 was obtained as colorless crystals according to the procedure described in Example 1. The phase transition temperature (° C.) of this compound is shown below.
The numbers in parentheses indicate the phase transition temperatures during the cooling process. Example 10: Preparation of liquid crystal composition The following compound group (Formula 11) was mixed at the ratio shown below, and heated and melted at 100 ° C to prepare a liquid crystal composition (ferroelectric liquid crystal composition). did.

[0084]

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

Example 11: Preparation of a 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 0.2 g of γ-glycidyloxypropyltrimethoxysilane was further formed. Surface treatment was performed using a 2% by weight ethanol solution. The glass plate with the ITO film was spin-coated with polyvinyl alcohol to form a film, and baked at 120 ° C. for 30 minutes to form an insulating orientation control layer. This orientation control layer was subjected to a rubbing treatment, and silica beads having an average particle size of 1.9 μm were sprayed on one glass plate. Thereafter, a glass plate was bonded using a sealant so that the respective rubbing treatment axes were antiparallel to each other, thereby producing a cell. This cell was heated to 100 ° C., the liquid crystal composition prepared in Example 10 heated (100 ° C.) was injected, and then cooled at a rate of 3 ° C./min to produce a liquid crystal element. When this liquid crystal element was sandwiched between two polarizing plates arranged in a crossed Nicols state and a rectangular wave of ± 20 V and 10 Hz was applied, a clear switching phenomenon was observed. In addition, a good uniform alignment state was observed with a polarizing microscope, and no alignment defects such as zigzag defects were observed. The optical response time at room temperature (25 ° C.) was 118 μsec.

[0086]

According to the present invention, as a component of a liquid crystal composition, it has a wide liquid crystal temperature range and has an effect of improving the response time, alignment characteristics, etc. of the liquid crystal composition when added to the liquid crystal composition. It has become possible to provide useful naphthalene compounds.

[Brief description of the drawings]

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

[Explanation of symbols]

1: Liquid crystal layer having a chiral smectic phase 2: Substrate 3: Transparent electrode 4: Insulating alignment control layer 5: Spacer 6: Lead wire 7: Power 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 Toatsu Chemicals Co., Ltd.

Claims (3)

[Claims] 1. A naphthalene compound represented by the general formula (1). Embedded image [In the formula, Y ₁ represents a single bond or a —O— group; Y ₂ represents a single bond, a —O— group, a —CO— group, a —COO— group, and a —O
Represents a group selected from the group consisting of a CO- group, wherein R ₁ , R ₂
Is a linear or branched alkyl group having 1 to 24 carbon atoms which may be substituted with a halogen atom, or a linear or branched unsaturated group having 2 to 24 carbon atoms which may be substituted with a halogen atom. Alkyl groups, straight-chain or branched-chain alkoxyalkyl groups having 2 to 24 carbon atoms which may be substituted by halogen atoms or straight-chain or branched-chain alkoxyalkyl groups having 3 to 24 carbon atoms which may be substituted by halogen atoms. Represents a saturated alkoxyalkyl group, R ₁ and R ₂ may have an asymmetric carbon, and the asymmetric carbon may be optically active; X represents a hydrogen atom or a halogen atom; Or 1) 2. A liquid crystal composition comprising at least one kind of the naphthalene compound according to claim 1. 3. A liquid crystal device comprising the liquid crystal composition according to claim 2.