JP2743506B2 - Optically active ester derivative, method for producing the same, liquid crystal composition containing the same as active ingredient, and liquid crystal device using the same - Google Patents

Description

The present invention relates to an optically active ester derivative useful as a compounding component of a ferroelectric liquid crystal composition, a method for producing the same, and a liquid crystal composition using the same as an active ingredient. And a liquid crystal element using the same.

<Conventional Technology> At present, a TN (twisted nematic) type display system is most widely used as a liquid crystal display device. This TN liquid crystal display has many advantages such as low driving voltage and low power consumption. However, in terms of response speed, it is inferior to light-emitting display devices such as cathode-ray tubes, electroluminescence, and plasma displays. A new TN type display element having a twist angle of 180 to 270 ° has also been developed, but the response speed is still inferior. Although various improvements have been made in this way, a TN type display element having a high response speed has not yet been developed. However, a new display system using ferroelectric liquid crystal, which has been actively researched recently, may improve the response speed (Clark et al .: Ap
plid Phys.lett., 86 , 899 (1980)). This method uses a chiral smectic phase such as a chiral smectic C phase exhibiting ferroelectricity (hereinafter, abbreviated as Sc ^* phase).

However, a liquid crystal material having sufficient spontaneous polarization necessary for high-speed response and having a Sc ^* phase in a lower temperature range and a wider temperature range has not been found so far.

<Problems to be Solved by the Invention> It is an object of the present invention to provide a ferroelectric liquid crystal material which has a sufficient spontaneous polarization, can respond at high speed, and exhibits liquid crystallinity in a lower temperature range.

<Means for Solving the Problem> That is, the present invention provides a compound represented by the general formula (I): (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, and R ₂ represents an optically active alkyl group or alkoxyalkyl having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms. X represents -COO- or -OCO-, Y represents -O-, -COO- or -OCO-, and 1 represents 1
Or 2, and m is 0 or 1. n is 3 to 6
Is an integer up to. k is 0 or 1. ), A method for producing the same, a liquid crystal composition containing the same as an active ingredient, and a liquid crystal device using the same.

 Hereinafter, the present invention will be described in detail.

X of the optically active ester derivative (I) of the present invention is -OC
The compound represented by O- can be produced by the following method.

That is, the general formula (II) (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, and Y represents-
O-, -COO- or -OCO- is shown. l is 1 or 2, and m is 0 or 1. ) And a phenol represented by the general formula (III) (In the formula, R ₂ represents an optically active alkyl or alkoxyalkyl group having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms, and R ′ represents a hydroxyl group or a halogen atom. n is an integer from 3 to 6. k is 0 or 1.) which is obtained by reacting an optically active benzoic acid. Most of the phenols (II) are known compounds and can be produced according to the method described in the literature.

Such phenols (II) include 4-alkoxyphenol, 4-alkylphenol, 4'-alkoxy-4-hydroxybiphenyl, 4'-alkyl-4-
Hydroxybiphenyl, 4-alkoxycarbonylphenol, 4-alkylcarbonyloxyphenol,
4'-alkoxycarbonyl-4-hydroxybiphenyl and 4'-alkylcarbonyloxy-4-hydroxybiphenyl are exemplified.

Here, each of the above alkyls or alkoxys has a linear alkyl group having 3 to 20 carbon atoms,
Specific examples of the alkyl group are as follows.

Propyl, butyl, pentyl, hexyl, heptyl,
Octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl.

These phenols are converted to metal phenolates and can be reacted with the optically active carboxylic acids (III).

The other material, optically active benzoic acid (III),
The novel compounds discovered by the present inventors for the first time can be produced, for example, by the following method.

(In the above reaction formula, R ″ represents a methyl group.) (In the above reaction formula, R ″ represents a methyl group, Z represents a tetrahydropyranyl group, a t-butyldimethylsilyl group, a benzyl group, and the like.) Such optically active benzoic acids (III) include
4- (3-alkoxypropylbenzoic acid, 4- (4-alkoxybutyl) benzoic acid, 4- (5-alkoxypentyl) benzoic acid, 4- (6-alkoxyhexyl) benzoic acid, 4- (3-alkoxyalkoxy) Propyl) benzoic acid, 4- (4-alkoxyalkoxybutyl) benzoic acid, 4- (5-alkoxyalkoxypentyl) benzoic acid, 4- (6-alkoxyalkoxyhexyl) benzoic acid, 4- (3-alkanoyloxypropyl) Benzoic acid, 4- (4-alkanoyloxybutyl) benzoic acid,
4- (5-alkanoyloxypentyl) benzoic acid, 4
-(6-alkanoyloxyhexyl) benzoic acid, 4-
(3-alkoxyalkanoyloxypropyl) benzoic acid, 4- (4-alkoxyalkanoyloxybutyl)
Examples are benzoic acid, 4- (5-alkanoyloxypentyl) benzoic acid and 4- (6-alkoxyalkanoyloxyhexyl) benzoic acid.

Here, the above alkoxy, alkoxyalkoxy,
Alkanoyloxy or alkoxyalkanoyloxy is represented by the aforementioned general formula (III) And the substituent R ₂ is an optically active alkyl group or alkoxyalkyl group having an asymmetric carbon atom which may be substituted by a halogen atom having 3 to 15 carbon atoms.

When k = 0, the upper alkyl group or alkoxyalkyl group is specifically 1-methylpropyl, 2-methylbutyl, 1-methylbutyl, 2,3-dimethylbutyl, 1,2-dimethylbutyl, -Dimethylbutyl, 2,3,
3-trimethylbutyl, 2-methylpentyl, 3-methylpentyl, 1,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 2,3,3,4-tetramethylpentyl, 1- Methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 1,2-
Dimethylhexyl, 2,5-dimethylhexyl, 1,3-dimethylheptyl, 2-methylheptyl, 5-methylheptyl, 2-methyloctyl, 1,2-dimethyloctyl, 1,4
-Dimethyloctyl, 1-methylnonyl, 2-methylnonyl, 3-methylnonyl, 4-methylnonyl, 5-methylnonyl, 6-methylnonyl, 7-methylnonyl, 1,2
-Dimethylnonyl, 1-methyldecyl, 2-methyldecyl, 3-methyldecyl, 4-methyldecyl, 5-methyldecyl, 6-methyldecyl, 7-methyldecyl, 8-methyldecyl, 1-methylundecyl, 9-methylundecyl, 1- Methyl dodecyl, 10-methyl dodecyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyhexyl, methoxyheptyl,
Methoxyoctyl, methoxynonyl, methoxydecyl,
Ethoxyethyl, ethoxypropyl, ethoxybutyl,
Ethoxypentyl, ethoxyhexyl, ethoxyheptyl, ethoxyoctyl, ethoxynonyl, ethoxydecyl, propoxyethyl, propoxypropyl, propoxybutyl, propoxypentyl, propoxyhexyl, propoxyheptyl, propoxyoctyl, propoxynonyl, propoxydecyl, butoxyethyl Propyl, butoxybutyl, butoxypentyl, butoxyhexyl, butoxyheptyl, butoxyoctyl, butoxynonyl, butoxydecyl, pentyloxyethyl, pentyloxypropyl, pentyloxybutyl, pentyloxypentyl, pentyloxyhexyl, pentyloxyoctyl, pentyloxydecyl ,
Hexyloxyethyl, hexyloxypropyl, hexyloxybutyl, hexyloxypentyl, hexyloxyhexyl, hexyloxyoctyl, heptyloxyethyl, heptyloxypropyl, heptyloxybutyl, heptyloxypentyl, octyloxyethyl, octyloxypropyl, decyloxy Ethyl, decyloxypropyl and the like can be mentioned. Further, 2-trihalomethylpentyl, 2-trihalomethylhexyl,
2-trihalomethylhepsyl, 2-halopropyl, 3-
Halo-2-methylpropyl, 2,3-dihalopropyl, 2
-Halobutyl, 3-halobutyl, 2,3-dihalobutyl,
2,4-dihalobutyl, 3,4-dihalobutyl, 2-halo-3
-Methylbutyl, 2-halo-3,3-dimethylbutyl, 2
-Halopentyl, 3-halopentyl, 4-halopentyl, 2,4-dihalopentyl, 2,5-dihalopentyl, 2-
Halo-3-methylpentyl, 2-halo-4-methylpentyl, 2-halo-3-monohalomethyl-4-methylpentyl, 2-halohexyl, 3-halohexyl, 4-halohexyl, 5-halohexyl, 2-haloheptyl, 2 −
Halooctyl (however, halo in the above alkyl group represents fluorine, chlorine, bromine or iodine) and the like.

When k = 1, 1-halopropyl, 1-halobutyl, 1-halopentyl,
Halohexyl, 1-haloheptyl, 1-halooctyl,
1-halo-2-methylpropyl, 1-halo-2-methylbutyl, 1-halo-2-methylpentyl, 1-halo-2
-Methylhexyl, 1-halo-2-methylheptyl, 1
-Halo-2-methyloctyl and the like.

The alcohol R ₂ OH having such a substituent R ₂ {described in the production example of the optically active benzoic acid (III) as the starting compound of the present invention (when k = 0)} indicates that the corresponding ketone is not It is easily obtained by asymmetric reduction with a chiral metal catalyst, a microorganism or an enzyme. Some can also be derived from the following optically active amino acids and optically active oxyacids that are naturally occurring or obtained by resolution.

Valine, leucine, isoleucine, phenylalanine, threonine, alosreonine, homoserine, alloisoleucine, tert-leucine, 2-aminobutyric acid, norvaline, norleucine, ornithine, lysine, hydroxylysine, phenylglycine, aspartic acid, glutamic acid, mandelic acid, tropha Acid, 3-hydroxybutyric acid, malic acid, tartaric acid, isopropylmalic acid and the like.

Further, a carboxylic acid R ₂ COOH having a substituent R _2, which has already been described in the production examples of optically active benzoic acids (III) as raw material compounds of the present invention (when k = 1),
Obtained by oxidation of the corresponding alcohol and reductive deamination of the amino acid. Others can be derived from the optically active amino acids and optically active oxy acids exemplified above, which are naturally occurring or obtained by resolution. Carboxylic acid having a substituent R ² obtained here, optionally induced by a known method the acid chloride, the carboxylic acid derivative such as an acid Puromido and acid anhydrides may be used.

Phenols (II) and optically active benzoic acids (III)
Can be applied by a usual esterification method, and can be carried out by using a catalyst in the presence or absence of a solvent using a catalyst.

When a solvent is used in this reaction, examples of the solvent include aliphatic solvents such as tetrahydrofuran, ethyl ether, acetone, methyl ethyl ketone, toluene, benzene, chlorobenzene, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, dimethylformamide, hexane and pyridine. Or aromatic hydrocarbons,
Solvents that are inert to the reaction, such as ethers, halogenated hydrocarbons, and organic amines, alone or in mixtures. The amount can be used without any particular limitation.

In the above reaction, when the optically active benzoic acid (III) is relatively expensive, in order to effectively use it,
It is preferable to carry out the reaction by using an excess amount of the phenol (II) as a partner raw material.
It is used up to 4 equivalents, preferably 1 to 2 equivalents.

Examples of the catalyst include dimethylaminopyridine, triethylamine, tri-n-butylamine, pyridine,
Organic or inorganic basic substances such as picoline, lysine, imidazole, sodium carbonate, sodium methylate, potassium hydrogen carbonate and the like can be mentioned.

Further, an organic acid or an inorganic acid such as toluenesulfonic acid, methanesulfonic acid, or sulfuric acid can be used as a catalyst.

The amount of the catalyst used varies depending on the type of each reaction raw material used and the combination of the catalyst used, etc., and cannot always be specified. For example, when an acid halide is used, the amount of the basic compound is at least one equivalent of the acid halide. The substance is used.

Furthermore, when the optically active benzoic acid represented by the general formula (III) is an optically active benzoic acid, N, N'-dicyclohexylcarbodiimide, N-cyclohexyl-
Carbodiimides such as N '-(4-diethylamino) cyclohexylcarbodiimide are preferably used as a condensing agent, and if necessary, 4-pyrrolidinopyridine, pyridine,
An organic base such as triethylamine can be used in combination.

In this case, the amount of the condensing agent used is usually 1 to 1.2 equivalent times based on the optically active benzoic acid, and when an organic base is used in combination, the amount of the organic base used is 0.01 to 0.2 equivalent times based on the condensing agent. is there.

Phenols (II) and optically active benzoic acids (III)
The reaction temperature in the reaction with is usually -80 ° C to 100 ° C, preferably -25 ° C to 80 ° C.

 The reaction time is not particularly limited.

After completion of the reaction, usual separation means such as extraction, liquid separation,
The desired general formula (I) is obtained from the reaction mixture by concentration or the like.
(However, X is -OCO-) The optically active ester derivative represented by-can be isolated, and can be purified by column chromatography, recrystallization or the like, if necessary. Specific examples of the thus obtained optically active ester derivative {in the case where X is —OCO— in the general formula (I)} are specifically exemplified by the following compounds.

4- [3-alkyl (C 3-15) oxypropyl
Ru] benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)
Phenyl ester, 4- [4-alkyl (C 3-15) oxybutyi
Ru] benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)
B) phenyl ester, 4- [5-alkyl (C3-15) oxypentene
Ru] benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)
C] phenyl ester, 4- [6-alkyl (C3-15) oxyhexyl
Ru] benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)
C) phenyl ester, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)]
Nylester, 4- [4-alkyl (C3-15) oxybutyi
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)]
Nylester, 4- [5-alkyl (C3-15) oxypentene
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)]
Nyl ester, 4- [6-alkyl (C 3-15) oxyhexyl
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)]
Nylester, 4- [3-alkyl (C 3-15) oxypropyl
Benzoic acid 4 '-[alkyl (C3-20) oxo]
B) biphenylyl ester, 4- [4-alkyl (C3-15) oxybutyi
Benzoic acid 4 '-[alkyl (C3-20) oxo]
[C] biphenylyl ester, 4- [5-alkyl (3-15 carbon) oxypentene
Benzoic acid 4 '-[alkyl (C3-20) oxo]
B) biphenylyl ester, 4- [6-alkyl (3 to 15 carbon atoms) oxyhexyl
Benzoic acid 4 '-[alkyl (C3-20) oxo]
B) biphenylyl ester, 4- [3-alkyl (3-15 carbon) oxypropyl
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)] bif
Enylyl ester, 4- [4-alkyl (C3-15) oxybutyi
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)] bif
Enylyl ester, 4- [5-alkyl (C3-15) oxypentene
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)] bif
Phenylyl ester, 4- [6-alkyl (3 to 15 carbon atoms) oxyhexyl
Benzoic acid 4- [alkyl (having 3 to 20 carbon atoms)] bif
Enylyl ester, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)]
Nylcarboxylate, 4- [4-alkyl (C3-15) oxybutyi
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)]
Nylcarboxylic acid ester, 4- [5-alkyl (C 3-15) oxypentene
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)]
Nylcarboxylic acid ester, 4- [6-alkyl (C3-15) oxyhexyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)]
Nylcarboxylic acid ester, 4- [3-alkyl (C 3-15) oxypropyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
B) phenylcarboxylic acid ester, 4- [4-alkyl (C3-15) oxybutyi
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
B] phenylcarboxylate, 4- [5-alkyl (3-15 carbon) oxypentene
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
B) phenylcarboxylic acid ester, 4- [6-alkyl (C3-15) oxyhexyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
B) phenylcarboxylic acid ester, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl
L] phenyl 4 '-[alkyl (having 3 to 20 carbon atoms)
B] biphenylcarboxylic acid ester, 4- [4-alkyl (C3-15) oxybutyi
L] phenyl 4 '-[alkyl (having 3 to 20 carbon atoms)
B] biphenylcarboxylic acid ester, 4- [5-alkyl (3-15 carbon) oxypentene
L] phenyl 4 '-[alkyl (having 3 to 20 carbon atoms)
B] biphenylcarboxylic acid ester, 4- [6-alkyl (C3-15) oxyhexyl
L] phenyl 4 '-[alkyl (having 3 to 20 carbon atoms)
B] biphenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) oxypropyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)] bif
Phenyl carboxylate, 4- [4-alkyl (C 3-15) oxybutyi
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)] bif
Phenyl carboxylate, 4- [5-alkyl (C 3-15) oxypentene
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)] bif
Phenyl carboxylate, 4- [6-alkyl (3 to 15 carbon atoms) oxyhexyl
L] phenyl 4- [alkyl (having 3 to 20 carbon atoms)] bif
Phenyl carboxylate, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] phenyl ester, 4- [4-alkyl (C 3-15) oxybutyi
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] phenyl ester, 4- [5-alkyl (C 3-15) oxypentene
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] phenyl ester, 4- [6-alkyl (C 3-15) oxyhexyl
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] phenyl ester, 4- [3-alkyl (C 3-15) oxypropyl
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] biphenylyl ester, 4- [4-alkyl (C 3-15) oxybutyi
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] biphenylyl ester, 4- [5-alkyl (C 3-15) oxypentene
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] biphenylyl ester, 4- [6-alkyl (C 3-15) oxyhexyl
L] benzoic acid 4- [alkyl (C3-C20) oxy
Carbonyl] biphenylyl ester, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
4- [alkyloxypropyl] benzoate (C3-C20
Oxy) phenyl ester, 4- [4-alkoxyalkyl (C3-15) O
4- [alkyl benzoyl] benzoate (C3-C20
Oxy) phenyl ester, 4- [5-alkoxyalkyl (C3-C15)
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxy) phenyl ester, 4- [6-alkoxyalkyl (C3-C15)
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxy) phenyl ester, 4- [3-alkoxyalkyl (C3-15) O
4- [alkyloxypropyl] benzoate (C3-C20
)] Phenyl ester, 4- [4-alkoxyalkyl (C3-15) O
4- [alkyl benzoyl] benzoate (C3-C20
)] Phenyl ester, 4- [5-alkoxyalkyl (C3-15) O
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
)] Phenyl ester, 4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
)] Phenyl ester, 4- [3-alkoxyalkyl (C3-15) O
Xypropyl] benzoic acid 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylyl ester, 4- [4-alkoxyalkyl (C 3-15)
Xybutyl] benzoic acid 4 '-[alkyl (C3-C20
Oxy) biphenylyl ester, 4- [5-alkoxyalkyl (C3-C15)
Xypentyl] benzoic acid 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylyl ester, 4- [6-alkoxyalkyl (C3-15) O
Xyhexyl] benzoic acid 4 '-[alkyl (C3-C3)
20) oxy] biphenylyl ester, 4- [3-alkoxyalkyl (C3-15) O
4- [alkyloxypropyl] benzoate (C3-C20
)] Biphenylyl ester, 4- [4-alkoxyalkyl (C3-C15)
4- [alkyl benzoyl] benzoate (C3-C20
)] Biphenylyl ester, 4- [5-alkoxyalkyl (C3-C15)
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
)] Biphenylyl ester, 4- [6-alkoxyalkyl (C3-C15)
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
)] Biphenylyl ester, 4- [3-alkoxyalkyl (C3-C15)
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
)] Phenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C3-15) O
Xybutyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15) O
Xypentyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C3-15) O]
Xyhexyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15) O
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
Oxy) phenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C3-15) O]
Xybutyl] phenyl 4- [alkyl (C 3-20
Oxy] phenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15) O]
Xypentyl] phenyl 4- [alkyl (C 3-20
Oxy] phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C3-15) O]
Xyhexyl] phenyl 4- [alkyl (C 3-20
Oxy) phenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15) O]
Xypropyl] phenyl 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C 3-15)
Xybutyl] phenyl 4 '-[alkyl (C3-C20
Oxy) biphenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15) O]
Xypentyl] phenyl 4 '-[alkyl (having a carbon number of 3 to
20) oxy] biphenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C 3-15)
Xyhexyl] phenyl 4 '-[alkyl (having a carbon number of 3 to
20) oxy] biphenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15) O
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
)] Biphenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C 3-15)
Xybutyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15)
Xypentyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C 3-15)
Xyhexyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15)
4- [alkyloxypropyl] benzoate (C3-C20
Oxycarbonyl] phenyl ester, 4- [4-alkoxyalkyl (C3-15) O
4- [alkyl benzoyl] benzoate (C3-C20
Oxycarbonyl] phenyl ester, 4- [5-alkoxyalkyl (C3-15) O
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxycarbonyl] phenyl ester, 4- [6-alkoxyalkyl (C3-15) O]
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxycarbonyl] phenyl ester, 4- [3-alkoxyalkyl (C3-15) O
4- [alkyloxypropyl] benzoate (C3-C20
Oxycarbonyl] biphenylyl ester, 4- [4-alkoxyalkyl (C3-15) O]
4- [alkyl benzoyl] benzoate (C3-C20
Oxycarbonyl] biphenylyl ester, 4- [5-alkoxyalkyl (C3-15) O]
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxycarbonyl] biphenylyl ester, 4- [6-alkoxyalkyl (C3-15) O]
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxycarbonyl] biphenylyl ester, 4- [3-alkyl (C3-15) carbonyl]
4- [alkyloxypropyl] benzoate (C3-C20
Oxy) phenyl ester, 4- [4-alkyl (C 3-15) carbonyl]
4- [alkyl benzoyl] benzoate (C3-C20
Oxy) phenyl ester, 4- [5-alkyl (C3-15) carbonyl]
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxy] phenyl ester, 4- [6-alkyl (C3-15) carbonyl]
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxy) phenyl ester, 4- [3-alkyl (C3-15) carbonyl]
4- [alkyloxypropyl] benzoate (C3-C20
)] Phenyl ester, 4- [4-alkyl (C 3-15) carbonyl)
4- [alkyl benzoyl] benzoate (C3-C20
)] Phenyl ester, 4- [5-alkyl (C 3-15) carbonyl)
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
)] Phenyl ester, 4- [6-alkyl (C3-C15) carbonyl
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
)] Phenyl ester, 4- [3-alkyl (C 3-15) carbonyl
Xypropyl] benzoic acid 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylyl ester, 4- [4-alkyl (C 3-15) carbonyl
Xybutyl] benzoic acid 4 '-[alkyl (C3-C20
Oxy) biphenylyl ester, 4- [5-alkyl (C3-15) carbonyl]
Xypentyl] benzoic acid 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylyl ester, 4- [6-alkyl (C 3-15) carbonyl
Xyhexyl] benzoic acid 4 '-[alkyl (C3-C3)
20) oxy] biphenylyl ester, 4- [3-alkyl (3-15 carbon) carbonyl
4- [alkyloxypropyl] benzoate (C3-C20
)] Biphenylyl ester, 4- [4-alkyl (C 3-15) carbonyl
4- [alkyl benzoyl] benzoate (C3-C20
)] Biphenylyl ester, 4- [5-alkyl (C3-C15) carbonyl
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
)] Biphenylyl ester, 4- [6-alkyl (C3-C15) carbonyl
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
)] Biphenylyl ester, 4- [3-alkyl (C 3-15) carbonyl
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
)] Phenyl carboxylic acid ester, 4- [4-alkyl (C 3-15) carbonyl
Xybutyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [5-alkyl (C 3-15) carbonyl
Xypentyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [6-alkyl (C3-15) carbonyl]
Xyhexyl] phenyl 4- [alkyl (C 3-20
)] Phenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyl
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
Oxy] phenylcarboxylic acid ester, 4- [4-alkyl (C3-15) carbonyl]
Xybutyl] phenyl 4- [alkyl (C 3-20
Oxy] phenylcarboxylic acid ester, 4- [5-alkyl (C3-15) carbonyl]
Xypentyl] phenyl 4- [alkyl (C 3-20
Oxy] phenylcarboxylic acid ester, 4- [6-alkyl (C3-15) carbonyl]
Xyhexyl] phenyl 4- [alkyl (C 3-20
Oxy] phenylcarboxylic acid ester, 4- [3-alkyl (C3-15) carbonyl]
Xypropyl] phenyl 4 '-[alkyl (having 3 to 3 carbon atoms)
20) oxy] biphenylcarboxylic acid ester, 4- [4-alkyl (3-15 carbon) carbonyl
Xybutyl] phenyl 4 '-[alkyl (C3-C20
Oxy] biphenylcarboxylic acid ester, 4- [5-alkyl (C3-15) carbonyl]
Xypentyl] phenyl 4 '-[alkyl (having a carbon number of 3 to
20) oxy] biphenylcarboxylic acid ester, 4- [6-alkyl (C3-15) carbonyl]
Xyhexyl] phenyl 4 '-[alkyl (having a carbon number of 3 to
20) oxy] biphenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyl
Xypropyl] phenyl 4- [alkyl (having 3 to 20 carbon atoms)
)] Biphenylcarboxylic acid ester, 4- [4-alkyl (C3-15) carbonyl]
Xybutyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [5-alkyl (C 3-15) carbonyl
Xypentyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [6-alkyl (C 3-15) carbonyl)
Xyhexyl] phenyl 4- [alkyl (C 3-20
)] Biphenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyl
4- [alkyloxypropyl] benzoate (C3-C20
Oxycarbonyl] phenyl ester, 4- [4-alkyl (C3-15) carbonyl]
4- [alkyl benzoyl] benzoate (C3-C20
Oxycarbonyl] phenyl ester, 4- [5-alkyl (C 3-15) carbonyl)
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxycarbonyl] phenyl ester, 4- [6-alkyl (C3-15) carbonyl]
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxycarbonyl] phenyl ester, 4- [3-alkyl (C3-C15) carbonyl
4- [alkyloxypropyl] benzoate (C3-C20
Oxycarbonyl] biphenylyl ester, 4- [4-alkyl (C3-15) carbonyl]
4- [alkyl benzoyl] benzoate (C3-C20
Oxycarbonyl] biphenylyl ester, 4- [5-alkyl (C3-15) carbonyl]
Xypentyl] 4- [alkyl benzoate (having 3 to 20 carbon atoms)
Oxycarbonyl] biphenylyl ester, 4- [6-alkyl (C3-C15) carbonyl
Xyhexyl] 4- [alkyl benzoate (3-20 carbon atoms)
Oxycarbonyl] biphenylyl ester, 4- [3-alkoxyalkyl (C3-15))
Rubonyloxypropyl] benzoic acid 4- [alkyl (charcoal
Oxy] phenyl ester having a prime number of 3 to 20, 4- [4-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxybutyl] benzoic acid 4- [alkyl (carbon
Oxy] phenyl ester, 4- [5-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypentyl] 4- [alkyl benzoate (charcoal
Oxy] phenyl ester having a prime number of 3 to 20, 4- [6-alkoxyalkyl (having a carbon number of 3 to 15)
Rubonyloxyhexyl] benzoic acid 4- [alkyl (charcoal
Oxy] phenylester, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypropyl] benzoic acid 4- [alkyl (charcoal
Phenyl ester, 4- [4-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxybutyl] benzoic acid 4- [alkyl (carbon
Phenyl ester, 4- [5-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypentyl] 4- [alkyl benzoate (charcoal
Phenyl ester, 4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxyhexyl] benzoic acid 4- [alkyl (charcoal
Phenyl ester, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)]
Rubonyloxypropyl] benzoic acid 4 '-[alkyl
Oxy] biphenylyl ester (having 3 to 20 carbon atoms), 4- [4-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxybutyl] benzoic acid 4 '-[alkyl (charcoal
Oxy] biphenylyl ester having a prime number of 3 to 20; 4- [5-alkoxyalkyl (having a carbon number of 3 to 15)
Rubonyloxypentyl] benzoic acid 4 '-[alkyl
Oxy] biphenylyl ester (having 3 to 20 carbon atoms), 4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxyhexyl] benzoic acid 4 '-[alkyl
Oxy] biphenylyl ester (having 3 to 20 carbon atoms), 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypropyl] benzoic acid 4- [alkyl (charcoal
Biphenylyl ester, 4- [4-alkoxyalkyl (having 3 to 15 carbon atoms)]
Rubonyloxybutyl] benzoic acid 4- [alkyl (carbon
Biphenylyl ester, 4- [5-alkoxyalkyl (having 3 to 15 carbon atoms)]
Rubonyloxypentyl] 4- [alkyl benzoate (charcoal
Biphenylyl ester, 4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxyhexyl] benzoic acid 4- [alkyl (charcoal
Biphenylyl ester, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypropyl] phenyl 4- [alkyl (charcoal
Phenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C3-15)]
Rubonyloxybutyl] phenyl 4- [alkyl (carbon
Phenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15))
Rubonyloxypentyl] phenyl 4- [alkyl (charcoal
Phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C3-15)]
Rubonyloxyhexyl] phenyl 4- [alkyl (charcoal
Phenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15)]
Rubonyloxypropyl] phenyl 4- [alkyl (charcoal
Oxy] phenylcarboxylic acid ester having a prime number of 3 to 20), 4- [4-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxybutyl] phenyl 4- [alkyl (carbon
Oxy] phenylcarboxylic acid ester of the formula (3-20), 4- [5-alkoxyalkyl (C3-15))
Rubonyloxypentyl] phenyl 4- [alkyl (charcoal
Oxy] phenylcarboxylic acid ester having a prime number of 3 to 20), 4- [6-alkoxyalkyl (having a carbon number of 3 to 15)
Rubonyloxyhexyl] phenyl 4- [alkyl (charcoal
Oxy] phenylcarboxylic acid ester having 3 to 20 prime numbers, 4- [3-alkoxyalkyl (3 to 15 carbon atoms)
Rubonyloxypropyl] phenyl 4 '-[alkyl
(C3-C20) oxy] biphenylcarboxylic acid S
Ter, 4- [4-alkoxyalkyl (3-15 carbon atoms)
Rubonyloxybutyl] phenyl 4 '-[alkyl (charcoal
Oxy] biphenylcarboxylic acid ester having a prime number of 3 to 20)
4- [5-alkoxyalkyl (C 3-15)
Rubonyloxypentyl] phenyl 4 '-[alkyl
(C3-C20) oxy] biphenylcarboxylic acid S
Ter, 4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxyhexyl] phenyl 4 '-[alkyl
(C3-C20) oxy] biphenylcarboxylic acid S
Ter, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypropyl] phenyl 4- [alkyl (charcoal
A prime number of 3 to 20)] biphenylcarboxylic acid ester, 4- [4-alkoxyalkyl (of 3 to 15 carbon atoms)
Rubonyloxybutyl] phenyl 4- [alkyl (carbon
Biphenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C3-15)]
Rubonyloxypentyl] phenyl 4- [alkyl (charcoal
A prime number of 3 to 20)] biphenylcarboxylic acid ester, 4- [6-alkoxyalkyl (of 3 to 15 carbon atoms)
Rubonyloxyhexyl] phenyl 4- [alkyl (charcoal
A prime number of 3 to 20)] biphenylcarboxylic acid ester, 4- [3-alkoxyalkyl (of 3 to 15 carbon atoms)
Rubonyloxypropyl] benzoic acid 4- [alkyl (charcoal
Oxycarbonyl] phenylester having a prime number of 3 to 20, 4- [4-alkoxyalkyl (having a carbon number of 3 to 15)
Rubonyloxybutyl] benzoic acid 4- [alkyl (carbon
Oxycarbonyl] phenyl ester of the formula (3-20), 4- [5-alkoxyalkyl (C3-15))
Rubonyloxypentyl] 4- [alkyl benzoate (charcoal
Oxycarbonyl] phenyl ester having a prime number of 3 to 20, 4- [6-alkoxyalkyl (having a carbon number of 3 to 15)
Rubonyloxyhexyl] benzoic acid 4- [alkyl (charcoal
Oxycarbonyl] phenyl ester having a prime number of 3 to 20, 4- [3-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxypropyl] benzoic acid 4- [alkyl (charcoal
Oxycarbonyl] biphenylyl ester having a prime number of 3 to 20
4- [4-alkoxyalkyl (C 3-15)
Rubonyloxybutyl] benzoic acid 4- [alkyl (carbon
Oxycarbonyl] biphenylyl ester
4- [5-alkoxyalkyl (C 3-15)
Rubonyloxypentyl] 4- [alkyl benzoate (charcoal
Oxycarbonyl] biphenylyl ester having a prime number of 3 to 20
4- [6-alkoxyalkyl (having 3 to 15 carbon atoms)
Rubonyloxyhexyl] benzoic acid 4- [alkyl (charcoal
Oxycarbonyl] biphenylyl ester having a prime number of 3 to 20
Le.

In the above examples, alkyl (3 to 15 carbon atoms or 3 to 20 carbon atoms) and alkoxyalkyl (3 to 15 carbon atoms) include those exemplified above.

Next, the optically active ester derivative in which X is —COO— in the general formula (I) can be produced by the following method.

That is, the general formula (IV) (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, R ′ represents a hydroxyl group or a halogen atom. Y represents —O—, —COO
-Or -OCO-. l is 1 or 2, and m is 0 or 1. A carboxylic acid represented by the general formula (V): (Wherein, R ₂ represents an optically active alkyl or alkoxyalkyl group having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms, and n is an integer of 3 to 6) .K is 0 or 1.) by reacting an optically active phenol represented by the formula:

Most of the carboxylic acids (IV) are known compounds, and can be produced according to the method described in the literature.

Examples of the carboxylic acids (IV) include 4-alkoxybenzoic acid, 4-alkylbenzoic acid, 4'-alkoxy-4-biphenylcarboxylic acid, and 4'-alkyl-4.
-Biphenylcarboxylic acid, 4-alkoxycarbonylbenzoic acid, 4-alkylcarbonyloxybenzoic acid, 4 '
-Alkoxycarbonyl-4-biphenylcarboxylic acid,
4'-alkylcarbonyloxy-4-biphenylcarboxylic acids, and these carboxylic acids are also used as acid halides, that is, acid chlorides and acid bromides.

Here, the above-mentioned alkyl or alkoxy has a straight-chain alkyl group having 3 to 20 carbon atoms as described above.

The other material, optically active phenols (V),
The novel compounds discovered by the present inventors for the first time can be produced, for example, by the following method.

(In the formula, R ″ represents a methyl group.) Such optically active phenols (V) include:
For example, 4- (3-alkoxypropyl) phenol,
4- (4-alkoxybutyl) phenol, 4- (5-
(Alkoxypentyl) phenol, 4- (6-alkoxyhexyl) phenol, 4- (3-alkoxyalkoxypropyl) phenol, 4- (4-alkoxyalkoxybutyl) phenol, 4- (5-alkoxyalkoxypentyl) phenol, 4- (6-alkoxyalkoxyhexyl) phenol, 4- (3-alkanoyloxypropyl) phenol, 4- (4-alkanoyloxybutyl) phenol, 4- (5-alkanoyloxypentyl) phenol, 4- (6-alkanoyloxyhexyl) ) Phenol, 4- (3-alkoxyalkanoyloxypropyl) phenol, 4- (4-alkoxyalkanoyloxybutyl) phenol, 4-
Examples thereof include (5-alkoxyalkanoyloxypentyl) phenol and 4- (6-alkoxyalkanoyloxyhexyl) phenol, which can also be used as metal phenolate or tosylate.

Here, the above alkoxy, alkoxyalkoxy,
Alkanoyloxy and alkoxyalkanoyloxy are those represented by the general formula (V) And the substituent R ₂ includes those exemplified as R ₂ in the aforementioned general formula (III).

Carboxylic acids (IV) and optically active phenols (V)
Is reacted with the aforementioned general formula (I) (where X = —OCO
-) Can be carried out in the same manner as in the synthesis method.

However, relatively expensive optically active phenols (V)
In order to use effectively, it is preferable to carry out the reaction by using an excess amount of the carboxylic acid (IV) as a partner raw material, usually 1 to 4 equivalents, more preferably 1 to 2 equivalents. Used.

Further, when the carboxylic acid represented by the general formula (IV) is a carboxylic acid, the carboxylic acid represented by the general formula (I) (where X = —OCO
As in the case of-), carbodiimide is preferably used as the condensing agent, and the reaction conditions and the like can be similarly carried out.

The reaction temperature of the reaction between the carboxylic acids (IV) and the optically active phenols (V) is usually from -30 ° C to 10 ° C.
0 ° C., preferably -25 ° C. to 80 ° C.

 The reaction time is not particularly limited.

After the completion of the reaction, the desired optically active ester derivative represented by the general formula (I) (when X = —COO—) is isolated from the reaction mixture by a conventional separation means, for example, extraction, liquid separation, concentration and the like. It can be purified by column chromatography, recrystallization, etc., if necessary.

The optically active ester derivative thus obtained (however,
In the general formula (I), when X is -COO-),
The compound in which X is -COO- corresponding to the compound exemplified when X is -OCO- in the general formula (I) is mentioned above.

Examples of the ester derivative include the following compounds.

4- [3-alkyl (3 to 15 carbon atoms) oxypropyl] phenyl 4- [alkyl (3 to 20 carbon atoms) oxycarbonyl] phenylcarboxylic acid ester, 4- [4-alkyl (3 to 15 carbon atoms) Oxybutyl) phenyl 4- [alkyl (C3-20) oxycarbonyl] phenylcarboxylate, 4- [5-alkyl (C3-15) oxypentyl] phenyl4- [alkyl (C2 3- [20] oxycarbonyl] phenylcarboxylic acid ester, 4- [6-alkyl (3-15 carbon) oxyhexyl] phenyl 4- [alkyl (3-20 carbon) oxycarbonyl] phenylcarboxylic acid ester 4- [3-alkyl (C3-15) oxypropyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] biphenyl Ster, 4- [4-alkyl (C3-15) oxybutyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] biphenylcarboxylic acid ester, 4- [5-alkyl (C3-3) 15) oxypentyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] biphenylcarboxylic acid ester, 4- [6-alkyl (C3-15) oxyhexyl] phenyl 4- [alkyl ( Oxycarbonyl] biphenylcarboxylic acid ester of 3 to 20 carbon atoms, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] phenyl Ester, 4- [4-alkyl (C3-15) oxybutyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] phenyl Ester, 4- [5-alkyl (C3-15) oxypentyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] phenylester, 4- [6-alkyl (C3-3) 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] phenyl ester, 4- [3-alkyl (3 to 15 carbon atoms) oxypropyl] benzoic acid 4- [alkyl (15) oxyhexyl] benzoate C3-C20 carbonyloxy] biphenylyl ester, 4- [4-alkyl (C3-C15) oxybutyl] benzoic acid 4- [alkyl (C3-C20) carbonyloxy] biphenylyl ester 4- [5-alkyl (C3-15) oxypentyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] biphenylyl ester, 4- [6 -Alkyl (C3-15) oxyhexyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] biphenylyl ester, 4- [3-alkyl (C3-15) oxypropyl Phenyl 4- [alkyl (C3-20) carbonyloxy] phenylcarboxylic acid ester, 4- [4-alkyl (C3-15) oxybutyl] phenyl4- [alkyl (C3-20 ) Carbonyloxy] phenyl carboxylic acid ester, 4- [5-alkyl (C 3-15) oxypentyl] phenyl 4- [alkyl (C 3-20) carbonyloxy] phenyl carboxylic acid ester, 4- [ 6-alkyl (3 to 15 carbon atoms) oxyhexyl] phenyl 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] phenylcarboxylic acid ester 4- [3-alkyl (C3-15) oxypropyl] phenyl 4- [alkyl (C3-20) carbonyloxy] biphenylcarboxylate; 4- [4-alkyl (C3-3) 15) oxybutyl] phenyl 4- [alkyl (C3-20) carbonyloxy] biphenylcarboxylate; 4- [5-alkyl (C3-15) oxypentyl] phenyl4- [alkyl (carbon Carbonyloxy] biphenylcarboxylic acid ester of the formula (3-20), 4- [6-alkyl (C3-15) oxyhexyl] phenyl 4- [alkyl (C3-20) carbonyloxy] biphenylcarboxylic acid Ester, 4- [3-alkoxyalkyl (C 3-15) oxypropyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C3-15) oxybutyl] phenyl4- [alkyl (C3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [5-alkoxyalkyl (C 3-15) oxypentyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (3-15 carbon atoms) oxyhexyl] phenyl 4- [alkyl (3-20 carbon atoms)
Oxycarbonyl] phenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15) oxypropyl] phenyl4- [alkyl (C3-20
Oxycarbonyl] biphenyl ester, 4- [4-alkoxyalkyl (C 3-15) oxybutyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [5-alkoxyalkyl (3 to 15 carbon atoms) oxypentyl] phenyl 4- [alkyl (3 to 20 carbon atoms)
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [6-alkoxyalkyl (C 3-15) oxyhexyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [3-alkoxyalkyl (C3-15) oxypropyl] benzoic acid 4- [alkyl (C3-20
Carbonyloxy] phenyl ester, 4- [4-alkoxyalkyl (C3-C15) oxybutyl] benzoic acid 4- [alkyl (C3-C20)
Carbonyloxy] phenyl ester, 4- [5-alkoxyalkyl (C 3-15) oxypentyl] benzoic acid 4- [alkyl (C 3-20
Carbonyloxy] phenyl ester, 4- [6-alkoxyalkyl (C3-15) oxyhexyl] benzoic acid 4- [alkyl (C3-20
Carbonyloxy] phenyl ester, 4- [3-alkoxyalkyl (C3-C15) oxypropyl] benzoic acid 4- [alkyl (C3-C20)
Carbonyloxy] biphenylyl ester, 4- [4-alkoxyalkyl (C3-C15) oxybutyl] benzoic acid 4- [alkyl (C3-C20)
Carbonyloxy] biphenylyl ester, 4- [5-alkoxyalkyl (C3-C15) oxypentyl] benzoate 4- [alkyl (C3-C20)
Carbonyloxy] biphenylyl ester, 4- [6-alkoxyalkyl (C 3-15) oxyhexyl] benzoic acid 4- [alkyl (C 3-20
Carbonyloxy] biphenylyl ester, 4- [3-alkoxyalkyl (3-15 carbon atoms) oxypropyl] phenyl 4- [alkyl (3-20 carbon atoms)
Carbonyloxy] phenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C 3-15) oxybutyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] phenylcarboxylate, 4- [5-alkoxyalkyl (C3-15) oxypentyl] phenyl4- [alkyl (C3-20)
Carbonyloxy] phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (3-15 carbon atoms) oxyhexyl] phenyl 4- [alkyl (3-20 carbon atoms)
Carbonyloxy] phenylcarboxylic acid ester, 4- [3-alkoxyalkyl (3-15 carbon atoms) oxypropyl] phenyl 4- [alkyl (3-20 carbon atoms)
Carbonyloxy] biphenylcarboxylic acid ester, 4- [4-alkoxyalkyl (C3-15) oxybutyl] phenyl4- [alkyl (C3-20
Carbonyloxy] biphenyl carboxylate, 4- [5-alkoxyalkyl (C 3-15) oxypentyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] biphenylcarboxylic acid ester, 4- [6-alkoxyalkyl (3-15 carbon atoms) oxyhexyl] phenyl 4- [alkyl (3-20 carbon atoms)
Carbonyloxy] biphenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyloxypropyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [4-alkyl (C3-15) carbonyloxybutyl] phenyl4- [alkyl (C3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [5-alkyl (C 3-15) carbonyloxypentyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [6-alkyl (C3-15) carbonyloxyhexyl] phenyl4- [alkyl (C3-20
Oxycarbonyl] phenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyloxypropyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenyl ester, 4- [4-alkyl (C 3-15) carbonyloxybutyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [5-alkyl (C 3-15) carbonyloxypentyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [6-alkyl (C 3-15) carbonyloxyhexyl] phenyl 4- [alkyl (C 3-20
Oxycarbonyl] biphenylcarboxylic acid ester, 4- [3-alkyl (3 to 15 carbon atoms) carbonyloxypropyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] phenyl ester, 4- [4-alkyl (3 to 15 carbon atoms) carbonyloxybutyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] phenyl ester, 4- [5-alkyl (3 to 15 carbon atoms) carbonyloxypentyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] phenyl ester, 4- [6-alkyl (3 to 15 carbon atoms) carbonyloxyhexyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] phenyl ester, 4- [3-alkyl (3 to 15 carbon atoms) carbonyloxypropyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] biphenylyl ester, 4- [4-alkyl (3 to 15 carbon atoms) carbonyloxybutyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] biphenylyl ester, 4- [5-alkyl (3 to 15 carbon atoms) carbonyloxypentyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] biphenylyl ester, 4- [6-alkyl (3 to 15 carbon atoms) carbonyloxyhexyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] biphenylyl ester, 4- [3-alkyl (C 3-15) carbonyloxypropyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] phenylcarboxylic acid ester, 4- [4-alkyl (C 3-15) carbonyloxybutyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] phenylcarboxylic acid ester, 4- [5-alkyl (3 to 15 carbon atoms) carbonyloxypentyl] phenyl 4- [alkyl (3 to 20 carbon atoms)
Carbonyloxy] phenyl carboxylate, 4- [6-alkyl (C 3-15) carbonyloxyhexyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] phenylcarboxylic acid ester, 4- [3-alkyl (C 3-15) carbonyloxypropyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] biphenylcarboxylic acid ester, 4- [4-alkyl (C 3-15) carbonyloxybutyl] phenyl 4- [alkyl (C 3-20
Carbonyloxy] biphenylcarboxylate, 4- [5-alkyl (C3-15) carbonyloxypentyl] phenyl4- [alkyl (C3-20
Carbonyloxy] biphenylcarboxylate, 4- [6-alkyl (C3-15) carbonyloxyhexyl] phenyl4- [alkyl (C3-20
Carbonyloxy] biphenylcarboxylate, 4- [3-alkoxyalkyl (C3-15) carbonyloxypropyl] phenyl4- [alkyl (C3-20) oxycarbonyl] phenylcarboxylate, 4- [4-alkoxyalkyl (C3-15) carbonyloxybutyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] phenylcarboxylate, 4- [5-alkoxyalkyl (carbon number) 3- [15] carbonyloxypentyl] phenyl 4- [alkyl (3-20 carbon) oxycarbonyl] phenylcarboxylic acid ester, 4- [6-alkoxyalkyl (3-15 carbon) carbonyloxyhexyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] phenylcarbo Acid ester, 4- [3-alkoxyalkyl (C 3-15) carbonyloxypropyl] phenyl 4- [alkyl (C 3-20) oxycarbonyl] biphenyl ester, 4- [4-alkoxyalkyl (carbon Carbonyloxybutyl] phenyl 4- [alkyl (C3-20) oxycarbonyl] biphenylcarboxylate, 4- [5-alkoxyalkyl (C3-15) carbonyloxypentyl] Phenyl 4- [alkyl (3 to 20 carbon atoms) oxycarbonyl] biphenylcarboxylate; 4- [6-alkoxyalkyl (3 to 15 carbon atoms) carbonyloxyhexyl] phenyl 4- [alkyl (3 to 20 carbon atoms) 20) oxycarbonyl] biphenylcarboxylic acid ester, 4- [3-alkoxyalkyl 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] phenyl ester (3 to 15 carbon atoms) carbonyloxypropyl] benzoic acid 4- [4-alkoxyalkyl (3 to 15 carbon atoms) carbonyloxybutyl 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] phenyl ester, 4- [5-alkoxyalkyl (3 to 15 carbon atoms) carbonyloxypentyl] benzoic acid 4- [alkyl (3 carbon atoms) Carbonyloxy] phenyl ester, 4- [6-alkoxyalkyl (C3-15) carbonyloxyhexyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] phenyl ester, -[3-Alkoxyalkyl (C 3-15) carbonyloxypropyl] benzoic acid 4- [alkyl (C 3-20 ) Carbonyloxy] biphenylyl ester, 4- [4-alkoxyalkyl (C3-15) carbonyloxybutyl] benzoic acid 4- [alkyl (C3-20) carbonyloxy] biphenylyl ester, 4- [5-alkoxyalkyl (3 to 15 carbon atoms) carbonyloxypentyl] benzoic acid 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] biphenylyl ester, 4- [6-alkoxyalkyl (3 to 15 carbon atoms) 4- [alkyl (C3-20) carbonyloxy] biphenylyl ester, 4- [3-alkoxyalkyl (C3-15) carbonyloxypropyl] phenyl 4-) carbonyloxyhexyl] benzoate [Alkyl (C3-20) carbonyloxy] phenylcarboxylic acid ester, 4- [4-A Coxyalkyl (C3-15) carbonyloxybutyl] phenyl 4- [alkyl (C3-20) carbonyloxy] phenylcarboxylate, 4- [5-alkoxyalkyl (C3-15) carbonyl Oxypentyl] phenyl 4- [alkyl (C3-20) carbonyloxy] phenylcarboxylate, 4- [6-alkoxyalkyl (C3-15) carbonyloxyhexyl] phenyl4- [alkyl (carbon Carbonyloxy] phenylcarboxylic acid ester of the formula (3-20), 4- [3-alkoxyalkyl (C3-15) carbonyloxypropyl] phenyl 4- [alkyl (C3-20) carbonyloxy] biphenyl Carboxylic acid ester, 4- [4-alkoxyalkyl (C3-15) cal Nyloxybutyl] phenyl 4- [alkyl (C3-20) carbonyloxy] biphenylcarboxylate, 4- [5-alkoxyalkyl (C3-15) carbonyloxypentyl] phenyl 4- [alkyl ( Carbonyloxy] biphenylcarboxylic acid ester of 3 to 20 carbon atoms, 4- [6-alkoxyalkyl (3 to 15 carbon atoms) carbonyloxyhexyl] phenyl 4- [alkyl (3 to 20 carbon atoms) carbonyloxy] Biphenyl carboxylate.

In the above examples, alkyl (3 to 15 carbon atoms or 3 to 20 carbon atoms) and alkoxyalkyl (3 to 15 carbon atoms) include those exemplified above.

The optically active ester derivative represented by the general formula (I) (X is -OCO- or -C
OO-) is obtained, but when the derivative is used as a component of a liquid crystal, in particular, a component of a ferroelectric liquid crystal, the substituent of the general formula (I) is considered in consideration of practical optical stability and the like.
R ₂ is preferably an alkyl group containing no halogen atom. Further, for practical use, compounds having X = —COO— are preferred as those exhibiting more preferable physical properties.

Further, in order to exhibit the characteristic high-speed response in the ferroelectric liquid crystal, the liquid crystal compound preferably has a small viscosity coefficient. In the case of the compound represented by the general formula (I) according to the present invention, l = 1 is particularly preferred.

In the present invention, the liquid crystal composition contains at least one optically active compound represented by the general formula (I) as a compounding component. In this case, the optically active ester derivative represented by the general formula (I) is used in an amount of 0.1 to 99.9% by weight, particularly preferably 1 to 99% by weight of the obtained liquid crystal composition.
It is good to use in the ratio which becomes.

Further, by using such a liquid crystal composition, a liquid crystal element, for example, an optical switching element can be effectively used. In this case, a method of using the liquid crystal composition is not particularly limited, and a conventionally known method can be applied as it is. .

<Effect of the Invention> The optically active ester derivative represented by the general formula (I) has very excellent properties as a liquid crystal compound.
Its characteristics, by using the temperature range showing the Sc ^* phase is wide compound as one component of a liquid crystal composition, it is possible to spread the Sc ^* phase. Further, a compound having a small viscosity coefficient can increase the response speed of the liquid crystal element.

Due to the above excellent properties, the optically active ester derivative (I) of the present invention can be effectively used as a liquid crystal composition and further as a liquid crystal device using the same.

Further, according to the production method of the present invention, the optically active ester derivative (I) can be easily obtained at a high yield. Furthermore, the starting material for the optically active site of the optically active ester derivative (I) of the present invention is a relatively inexpensive compound, and many of them are commercially available. Therefore, the optically active ester derivative (I) of the present invention can be industrially advantageously obtained.

<Examples> Hereinafter, the present invention will be described with reference to examples, but the present invention is not particularly limited thereto.

Example 1 (+) in a four-necked flask equipped with a stirrer and a thermometer
-4- [3- (2 (s) -methylbutoxy) propyl]
1.11 g (5 mmol) of phenol, 1.67 g (6 mmol) of 4-decyloxybenzoic acid and 30 ml of anhydrous dichloromethane
And N, N'-dicyclohexylcarbodiimide 1.2
2 g (6 mmol) and 0.1 g of 4-pyrrolidinopyridine were added, and the mixture was stirred at room temperature for 24 hours.

After the completion of the reaction, the resulting precipitate was separated and diluted with 200 ml of toluene. The organic layer was formed of water, 5% acetic acid aqueous solution, water, 5% aqueous sodium bicarbonate solution,
After washing with water in that order, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate) to give (+)-4-decyloxybenzoic acid 4- [3
2.18 g (90.4% yield) of-(2 (s) -methylbutoxy) propyl] phenyl ester was obtained.

Example 2 (+) in a four-necked flask equipped with a stirrer and a thermometer
1.18 g (5 mmol) of -4- [4- (2 (s) -methylbutoxy) butyl] phenol and 20 ml of pyridine were charged, and the mixture was added at 20 to 25 ° C. with 4-octyloxybenzoic acid chloride.
1.7 g (6 mmol) were added and at the same temperature for 1 hour, then
The mixture was stirred at 40 ° C for 4 hours.

After completion of the reaction, the mixture was poured into 4N hydrochloric acid and extracted with 200 ml of toluene. The organic layer was washed with water, 5% aqueous sodium hydrogen carbonate and water in that order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; toluene-ethyl acetate) to give (+)-
2.28 g (yield 95%) of 4- [4- (2 (s) -methylbutoxy) butyl] phenyl ester of 4-octyloxybenzoic acid was obtained.

Example 3 1.04 g (5 mmol) of (+)-4- [3- (2s-butoxy) propyl] phenol was prepared in the same apparatus as in Example 1,
4'-octyloxy-4-biphenylcarboxylic acid 1.95
g (6 mmol) and 40 ml of chloroform were charged, and N, N'-
1.22 g (6 mmol) of dicyclohexylcarbodiimide
And 0.1 g of 4-pyrrolidinopyridine were added, and the mixture was stirred at room temperature for 24 hours.

Thereafter, post-treatment and purification were conducted in the same manner as in Example 1 to obtain 2.30 g of (+)-4'-octyloxy-4-biphenylcarboxylic acid 4- [3- (2s-butoxy) propyl] phenyl ester (yield: 89) %).

Example 4 (+)-4- [3- (2 (s)-
Methylbutoxy) propyl] benzoic acid (1.25 g, 5 mmol), 4-decyloxyphenol 1.50 g (6 mmol), anhydrous dichloromethane 25 ml and tetrahydrofuran 5 ml were charged, and N, N'-dicyclohexylcarbodiimide 1.13 g (5.5 mmol) and 4 -Pyrrolidinopyridine 0.05
g was added and the mixture was stirred at 25 to 35 ° C for 20 hours.

After completion of the reaction, the precipitate was separated, and post-treated and purified according to Example 1 to obtain (+)-4- [3- (2
(S) -Methylbutoxy) propyl] benzoic acid 4-decyloxyphenyl ester (2.19 g, yield 91%) was obtained.

Example 5 1.18 g of (+)-4- [3- (2 (s) -butoxy) propyl] benzoic acid in a four-neck flask 1.96 g (6 mmol) of 4'-decyloxy-4-biphenol and 40 ml of anhydrous dichloromethane And N, N'-dicyclohexylcarbodiimide 1.18 g (5.5 mmol) and pyridine 0.1 g
Was added and stirred at 30 to 35 ° C for 20 hours. Hereinafter, Example 1
By post-treatment and purification according to (+)-4-
[3- (2 (s) -butoxy) propyl] benzoic acid 4 '
2.89 g of decyloxybiphenylyl ester (8.8% yield)
%).

Examples 6 to 52 The reaction and post-treatment were carried out in the same manner as in Example 1 except that the raw materials used were changed to those shown in Table 1, and the results shown in Table 1 were obtained.

As shown in the above Examples, one of the compounds of the present invention
= 2 has a wide temperature range of the Sc ^* phase, and by using the compound as one of the components of the liquid crystal composition, the Sc ^* phase can be obtained ^.
It is possible to extend the temperature range of the phase.

Table 2 shows the viscosity coefficients of typical compounds among the compounds obtained in each of the above Examples. As is clear from the table, among the compounds of the present invention, the compound of l = 1 It can be seen that it has a small viscosity coefficient and is useful as a component for increasing the response speed of the liquid crystal composition.

Examples 53 and 54 (1) Liquid crystal compositions shown in Table 3 were prepared using liquid crystal compounds. The preparation was performed by mixing and weighing a predetermined compound in a sample bottle while heating and melting it in a sample bottle. Table 3 shows the phase series and the value of spontaneous polarization at 20 ° C. of the liquid crystal composition thus obtained.

(2) A polyimide-based polymer film is provided on a glass substrate on which an indium oxide transparent electrode is provided, and rubbed in a certain direction, and glass fibers (diameter 6 μm) such that the rubbing directions of the two substrates are parallel. Was used as a spacer to assemble a liquid crystal cell, and the liquid crystal composition was vacuum-sealed into the liquid crystal cell to obtain a liquid crystal element.

When this liquid crystal element was combined with a polarizer and electrolysis was applied to 20 V, a change in transmitted light intensity was observed. The response time at 20 ° C. was measured from the change in transmitted light intensity at this time.
The results are shown in Table-3.

As apparent from the results, by adding the liquid crystal compound of the present invention, Hakare the temperature drop of the Sc ^* phase, shows a Sc ^* phase at around room temperature, and the liquid crystal composition having excellent high-speed response is obtained Was confirmed.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C09K 19/20 C09K 19/20 // G02F 1/13 500 G02F 1/13 500 C07M 7:00 (72) Inventor Masayoshi Minai Osaka Sumitomo Chemical Co., Ltd., 3-1-1 98, Kasuganaka, Konohana-ku, Osaka (72) Inventor Kiyoshi Imamura 3-1-1, Kasuganaka, Konohana-ku, Osaka, Osaka Inventor Takeshi Tani 6th Kitahara, Tsukuba, Ibaraki Prefecture Sumitomo Chemical Co., Ltd. (72) Inventor Chitsu Kawakami 6th Kitahara, Tsukuba City, Ibaraki Sumitomo Chemical Co., Ltd. (72) Inventor Koichi Fujisawa Kitahara, Tsukuba City, Ibaraki Prefecture No. 6 Sumitomo Chemical Co., Ltd. (56) References JP-A-2-196755 (JP, A) JP-A-63-222148 (JP, A) JP-A-3-83949 (JP, A)

Claims (7)

(57) [Claims] (1) General formula (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, and R ₂ represents an optically active alkyl group or alkoxyalkyl having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms. X represents -COO- or -OCO-, Y represents -O-, -COO- or -OCO-, and 1 represents 1
Or 2, and m is 0 or 1. n is 3 to 6
Is an integer up to. k is 0 or 1. ) An optically active ester derivative represented by the formula: 2. The optically active ester derivative according to claim 1, wherein X is -OCO-. 3. The optically active ester derivative according to claim 1, wherein X is —COO—. 4. General formula (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, and Y represents-
O-, -COO- or -OCO- is shown. l is 1 or 2, and m is 0 or 1. ) And a phenol represented by the general formula (In the formula, R ₂ represents an optically active alkyl or alkoxyalkyl group having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms, and R ′ represents a hydroxyl group or a halogen atom. n is an integer from 3 to 6. k is 0 or 1.) The method for producing an optically active ester derivative according to claim 2, wherein the optically active benzoic acid is reacted. 5. The general formula (Wherein, R ₁ represents an alkyl group having 3 to 20 carbon atoms, R ′ represents a hydroxyl group or a halogen atom. Y represents —O—, —COO
-Or -OCO-. l is 1 or 2, and m is 0 or 1. ) And a carboxylic acid represented by the general formula (Wherein, R ₂ represents an optically active alkyl or alkoxyalkyl group having an asymmetric carbon atom which may be substituted with a halogen atom having 3 to 15 carbon atoms, and n is an integer of 3 to 6) And k is 0 or 1.) The method for producing an optically active ester derivative according to claim 3, wherein an optically active phenol represented by the following formula is reacted. 6. A liquid crystal composition comprising the optically active ester derivative according to claim 1 as at least one compounding component. 7. A liquid crystal device comprising a liquid crystal composition containing at least one optically active ester derivative according to claim 1 as a compounding component.