JPH06239775A - 4-@(3754/24)4-substituted aryl)-1,1-difluorohexane derivative, its production and liquid crystal composition containing the same - Google Patents

Abstract

PURPOSE:To obtain a stable and low-viscosity new liquid crystal compound high in physicochemical stability. CONSTITUTION:The objective compound of formula I [R is l-10C alkyl; Q is single bond, (thio)ether linkage or (thio)carbonic ester linkage; formula II is p-phenylene linkage, formula III, etc.; formula IV is p-phenylene linkage, formula III, formula V, etc.; (n) is 0-2; Z is single bond, (thio)carbonic ester linkage, etc.; when (n) is zero, Q and/or Z is single bond], e.g. a compound of formula VI. The compound of the formula I can be obtained by reaction between a compound of formula VII and a compound of formula VIII (Hal' is halogen).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel liquid crystal compound exhibiting a liquid crystal phase and having a low viscosity, a process for producing them, and a liquid crystal composition containing at least one of the compounds.

[0002]

2. Description of the Related Art Liquid crystal compounds exhibit dielectric anisotropy and optical anisotropy in the liquid crystal phase. The liquid crystal phase includes a nematic liquid crystal phase, a smectic liquid crystal phase, a cholesteric liquid crystal phase, etc. Among them, applied products using the nematic liquid crystal phase are most widely put into practical use. In other words, applied products that utilize these characteristics have been expanded to light control glass, sign displays, and flat panel displays such as calculators, watches, and word processors. With the recent advances in the electronics field, a wide variety of products (DS type) have been developed. , Twisted nematic type (TN type), super twisted nematic type (ST
N type), guest-host type (GH type) and the like.
The liquid crystal materials used for these are naturally physicochemically stable,
In particular, stability against heat, light, moisture, air, etc. is required. Further, the liquid crystal material has to exhibit a desired liquid crystal phase in a temperature range as wide as possible including room temperature, and physical properties such as operating voltage and responsiveness according to the purpose must be satisfied at a practical level. That is, it is generally preferable that the threshold voltage and the saturation voltage necessary for driving the liquid crystal display element are as low as possible, and that the viscosity of the liquid crystal material is as low as possible in order to increase the response speed. However, it is impossible to satisfy these physical properties with a single compound, and at present, several kinds of liquid crystal compounds and non-liquid crystal compounds are mixed to obtain the practically required properties. However, in order to construct a liquid crystal composition that satisfies these practically required properties, it is extremely important to develop a single compound having various properties as good as possible.

Under such circumstances, a compound exhibiting a nematic property is disclosed in, for example, JP-A-1-233239.

[0004]

[Chemical 10]

[R represents a C _1-15 alkyl group, n represents 1 or 2, X represents F or Cl. ] And the like have been proposed. However, these compounds do not satisfy the practically required properties.

[0006]

An object of the present invention is to provide a novel liquid crystal compound useful in developing such a practical liquid crystal composition.

[0007]

As a result of intensive studies to solve the above problems, the present inventors have succeeded in synthesizing a novel compound represented by the formula (I), and this compound ( It was discovered that I) had unexpectedly high physical and chemical stability and exhibited a stable nematic phase, and as a result of further studies, the present invention was completed.

That is, the present invention uses the formula (1)

[0009]

[Chemical 11]

[In the formula, R represents a linear or branched alkyl group having 1 to 10 carbon atoms, and Q represents a single bond, an ether bond, a thioether bond, a carboxylic acid ester bond or a thiocarboxylic acid ester bond. ,

[0011]

[Chemical 12]

N is 0, 1 or 2, Z is a single bond,
Carboxylic ester bond, thiocarboxylic ester bond,
A methyleneoxy bond or an oxymethylene bond is shown.
However, when n is 0, at least one of Q and Z represents a single bond. And a liquid crystal composition containing (3) compound (I) and (2) a method for producing compound (I).

Examples of the linear or branched alkyl group having 1 to 10 carbon atoms represented by R in the above formula (I) include, for example, methyl, ethyl, propyl,
Linear alkyl groups such as butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl , 1-methylpentyl, 2-methylpentyl, 5-methylhexyl, 2,3,5-trimethylhexyl, 2,
Branched alkyl groups such as 7,8-trimethyldecyl, 4-ethyl-5-methylnonyl and the like can be used. Of these, a linear alkyl group having 3 to 8 carbon atoms, such as propyl, butyl, pentyl, hexyl, heptyl, octyl and the like are preferable.

Q represents a single bond, an ether bond, a thioether bond, a carboxylic acid ester bond or a thiocarboxylic acid bond. In the carboxylic acid ester bond of the present invention,

[0015]

[Chemical 13]

N represents 0, 1 or 2, and preferably 0
Or 1.

Z represents a single bond, a carboxylic acid ester bond, a thiocarboxylic acid ester bond, a methyleneoxy bond or an oxyethylene bond. Z is preferably a single bond, a carboxylic acid ester bond or a thiocarboxylic acid ester bond, and particularly preferably a single bond or a carboxylic acid ester bond.

When n is 0, at least one of Q and Z represents a single bond. That is, when n is 0, the compound (I) has a partial structure

[0019]

[Chemical 14]

Next, a method for producing the compound (I) of the present invention will be described.

Production Method (1) [Compound (I) wherein Ring A is a Benzene Ring: Production Method of Compound (Ia)]

[0022]

[Chemical 15]

4-Phenylcyclohexane [1] obtained by a method known per se or a method analogous thereto is directly reacted with a known fluorination reaction [compound [1] by a fluorination agent such as diethylaminosulfur trifluoride (DAST). Or thioacetalizing the carbonyl group of compound [1] and then reacting with a suitable fluorination reaction reagent (for example, HF / pyridine)]
To give the difluoro compound [2]. As a solvent for the fluorination reaction, any solvent may be used as long as it does not inhibit the reaction, and it may not be used. The reaction temperature is about -20 ° C to 100 ° C, and usually 0 ° C to 50 ° C is preferably used. The reaction time is generally 2 minutes to 3 days, preferably 10 minutes to 24 hours, more preferably 10 minutes to 3 hours. The difluoro compound [2] thus synthesized is subjected to a Friedel-Crafts reaction known per se to obtain an acetyl compound [3]. The catalyst used in this Friedel-Crafts reaction is a Lewis acid (eg, AlCl ₃ , FeCl ₃ , SnCl ₄ , TiCl ₄ , BF
₃ OEt ₂ etc.). As the reaction solvent, any solvent may be used as long as it does not inhibit the reaction, and it may not be used. As such a reaction solvent, halogenated hydrocarbons (dichloromethane, 1,2-dichloroethane, etc.), nitroalkanes (nitromethane, nitroethane, etc.), nitrobenzene, etc. are used. The reaction temperature is -20 ° C to 100 ° C, and 0 ° C to 50 ° C is preferably used. The reaction time is generally 2 minutes to 3 days, preferably 10 minutes to 24 hours, more preferably 10 minutes to 3 hours. Then, the acetyl derivative [3] is oxidized (eg, haloform oxidation).
To obtain a carboxylic acid derivative [4]. This product [4] is subjected to a paraphrasing reaction (for example, direct chemical reduction with lithium aluminum hydride or the like, chemical reduction after esterification, etc.) to obtain a benzyl alcohol derivative [7]. On the other hand, a corresponding phenol derivative [5] is obtained by subjecting the above-mentioned acetyl derivative [3] to an oxidation reaction with peracid (eg, peracetic acid, formic acid, etc.).
To get

Intermediate [4] produced as described above
To [7] are subjected to a condensation reaction with various 4-substituted phenols, 4-substituted benzoic acids or 4-substituted benzyl alcohols to obtain the desired target compound (Ia) of the present invention.

[0025]

[Chemical 16]

Specifically, among such condensation reactions,
Esterification reaction (Z = carboxylic ester bond,

[0027]

[Chemical 17]

The target condensate can be produced by subjecting the phenolic compound or alcoholic compound to a dehydration condensation reaction in an organic solvent in the presence of a protic acid. As the halogen atom represented by Hal ′, for example, chlorine, bromine or iodine atom is used, and among them, chlorine or bromine atom is preferable. The reaction temperature is about -50 ° C to 100 ° C, and usually -20 ° C to 50 ° C is preferably used. The reaction time is usually 2 minutes to 3 days, preferably 10 minutes to
It is carried out for 24 hours, more preferably 10 minutes to 3 hours. Examples of the protic acid include inorganic acids such as sulfuric acid, hydrochloric acid and perchloric acid, organic sulfonic acids such as p-toluenesulfonic acid, benzenesulfonic acid, trifluoromethanesulfonic acid and methanesulfonic acid, or Amberlyst (trade name). The strongly acidic ion exchange resin can be used.
Examples of the organic solvent include hydrocarbons (hexane, benzene, toluene, etc.), halogenated hydrocarbons (chloroform, methylene chloride, carbon tetrachloride, 1,2-dichloroethane, etc.), ethers (diethyl ether, tetrahydrofuran, Dioxane), ethyl acetate, acetonitrile, dimethylformamide, etc. can be used. The carboxylic acid [4] is converted into an acid halide by using a halogenating reagent such as phosphorus pentachloride, thionyl chloride and thionyl bromide, and the halide is converted into a phenolic or alcoholic compound in the above organic solvent. Alternatively, the reaction may be carried out in the presence of a tertiary amine such as pyridine or triethylamine. In addition, alcohols are trimethylsilyl ether derivatives

[0029]

[Chemical 18]

It is also possible to condense with the acid halogenated derivative of the carboxylic acid [4] in the presence of a Lewis acid (eg zinc chloride) after the conversion to.

Further, for example, Mukaiyama reagents represented by N, N-dicyclohexylcarbodiimide (DCC), 1-methyl-2-halopyridinium iodide, diethyl ester of azodicarboxylic acid (DEAD) and triphenylphosphine (Ph ₂ The reaction between the carboxylic acid [4] and the alcohol can be promoted using a combination with P) (so-called Mitsunobu reagent) or an activating reagent such as triphenylphosphine dibromide. Reaction temperature is -5
It is carried out at about 0 ° C to 100 ° C, but usually -20 ° C to 50 ° C.
° C is preferred. The reaction time is usually 2 minutes to 3 days,
Preferably 10 minutes to 24 hours, more preferably 10 minutes to
It will take 3 hours.

These methods are described in, for example, Journal Organic Chemistry, 27 , 4675 (196).
2): Tetrahedron Letters, 1978 , 447.
5: Chemistry Letters, 1975 , 1145: Chemistry Letters, 1976 , 13: Bulletin
Chemical Society Japan, 50 , 1863
(1977), Bulletin Chemical Society
Japan, 40 , 2380 (1967): Synthetic Communication, 16 , 1423 (198).
6): Synthetic Communication, 16 , 6
59 (1986).

The compound (Ia) of the present invention can also be obtained by using the following condensation reaction.

[0034]

[Chemical 19]

The above reaction can be carried out in the same manner as the condensation reaction described above. As the halogen atom represented by Hal, for example, chlorine, bromine or iodine atom is used, and among them, chlorine or bromine atom is preferable. The starting compound can be produced by a method known per se or a method analogous thereto.

[0036]

[Chemical 20]

The thioester compound can be produced by using the thioalcohols and the conventional means as described above.

Z is an oxymethylene bond (--OCH _2- )
Alternatively, in the case of a methyleneoxy bond (—CH ₂ O—), the target ether form can be produced by subjecting a phenolic compound and an alcohol to an etherification reaction.

In this etherification reaction, the reaction itself is a known reaction, and the reaction can be carried out using a conventional means. For example, the reaction can be advanced using azodicarboxylic acid diethyl ester (DEAD) and triphenylphosphine (Ph ₂ P) (Pitner et al., Chemical and Industries, 1975 , 281). Also, alcohols (-CH
₂ OH) and an organic sulfonyl chloride are reacted in an organic solvent in the presence of an organic base such as pyridine or triethylamine or an inorganic base such as sodium hydride to give a corresponding organic sulfonic acid ester, and this ester is reacted with phenol. It may be reacted with a volatile compound. This reaction is carried out in an organic solvent in the presence of an inorganic base such as potassium carbonate or sodium hydride or an organic base such as pyridine or triethylamine. Examples of the organic sulfonyl chloride that can be used in this reaction include p-toluenesulfonic acid chloride, o-toluenesulfonic acid chloride, p-chlorobenzenesulfonic acid chloride, benzenesulfonic acid chloride, α-naphthalenesulfonic acid chloride, β- There are aromatic ring sulfonic acid chlorides such as naphthalene sulfonic acid chloride and aliphatic sulfonic acid chlorides such as methanesulfonic acid chloride and trifluoromethanesulfonic acid chloride. Examples of the organic solvent that can be used in this etherification reaction include aliphatic hydrocarbons (hexane, cyclohexane, etc.), halogenated hydrocarbons (chloroform, methylene chloride, carbon tetrachloride,
1,2-dichloroethane etc.), ethers (diethyl ether, tetrahydrofuran, dioxane etc.), aromatic hydrocarbons (benzene, toluene etc.), ethyl acetate, acetonitrile, dimethylformamide (DMF), dimethylsulfoxide (DMSO), hexa Methylphosphoric acid triamide (HMPA) and the like. The reaction temperature is -50 ° C
It is carried out at about 100 ° C, but normally -20 ° C to 50 ° C is preferably used. The reaction time is generally 2 minutes to 3 days, preferably 10 minutes to 24 hours, more preferably 10 minutes to 3 hours.

In the etherification reaction, alcohols (-
In order to activate (CH ₂ OH), there is a method of leading to a halogen derivative in addition to the above-mentioned method by sulfonic acid esterification. For example, the above-mentioned organic sulfonic acid ester can be converted into a halogen compound by reacting it with a metal halide salt (sodium iodide, potassium iodide, etc.).
Further, a halogenating agent such as phosphorus pentachloride, thionyl chloride or thionyl bromide may be directly acted on the alcohol (—CH ₂ OH). The halogen compound thus obtained and the phenolic compound can be reacted in an organic solvent in the presence of the above-mentioned inorganic base or organic base.

On the other hand, when Z is a single bond, it is described in the literature (for example,
Houben-Weill, “Methods of Organic Chemistry”, etc.), and known reaction conditions suitable for the reaction. For example, a Grignard reagent and an aromatic halogen compound are subjected to a coupling reaction in the presence of a catalyst such as a Pd complex, or trimethyl borate is allowed to act on the Grignard reagent to form a boric acid derivative, and then the aromatic compound is added in the presence of a Pd complex catalyst. It is produced by subjecting a halogen compound to a coupling reaction (see the following formula). Reaction temperature is -50 ° C
It is carried out at about -100 ° C, but usually -20 ° C to 50 ° C is preferably used. The reaction time varies depending on the reaction temperature and the reaction substrate, but is usually 2 minutes to 3 days, preferably 10 minutes to 2
It is carried out for 4 hours, more preferably 10 minutes to 3 hours.

[0042]

[Chemical 21]

(Hal, Hal ′ = halogen atom (eg Cl, Br, I etc.)) Further, the compound (I) in which the A ring is a pyrimidine ring is also obtained by the above method or a method analogous thereto. be able to.

Object (I) produced by the above method
Can be separated and purified from the reaction solution using a commonly used separation and purification means such as extraction, phase transfer, column chromatography, liquid chromatography, recrystallization and the like.

The compound (I) obtained as described above has high physical and chemical stability and has a stable nematic phase. Therefore, it is useful for a liquid crystal composition used for a liquid crystal flat panel display or the like. It can be used as one component. The compound of the present invention can be used alone as a liquid crystal compound, and by adding it to another liquid crystal mixture, the liquid crystal activity of the other liquid crystal mixture can be enhanced. As a liquid crystal mixture to which the compound of the present invention can be added, for example, “Flussige Kristalle in Tabellen” I & IIVEB Verl
ag, Leipzig or "Liquid Crystal Device Handbook" (edited by Japan Society for the Promotion of Science, 142th Committee, Nikkan Kogyo Shimbun) or "Full Color Liquid Crystal Display Technology" (Trikeps Publishing Department,
The nematic liquid crystal described in Trikeps Co., Ltd., etc., and a commercially available nematic liquid crystal compound are also included. In this case, the addition amount of the compound of the present invention is usually several% to 50%.
%, Preferably about 5% to 20%.

Hereinafter, the present invention will be described in more detail with reference to Examples, but these do not limit the scope of the present invention.

[0047]

【Example】

 Example 1

[0048]

[Chemical formula 22]

5.40 g of 4-phenylcyclohexanone
(0.030 mol) was dissolved in 20 ml of toluene, and diethylaminosulfur trifluoride (D
AST) 5.00 g (0.031 mol) are added. 45
After stirring at ~ 50 ° C for 7 hours, ether and NaHCO ₃ were added.
Extract by adding an aqueous solution. The organic layer was concentrated and then purified by silica gel chromatography (developing solution: n-hexane) to obtain 3.5 g (yield 59.5%) of the target product.

[0050]

[Chemical formula 23]

2.16 g (0.0) of the compound obtained in i)
11 mol), FeCl ₃ 2.67 g (0.016 mol)
Dissolve in 30 ml of H ₂ Cl ₂ and add 1.29 g (0.016 mol) of acetyl chloride while cooling with ice. After stirring for 1 hour, the reaction solution was poured into ice water, extracted with CH ₂ Cl ₂ , concentrated and purified by silica gel chromatography (developing solution: ethyl acetate / n-hexane = 5/95) to obtain the desired product 2.4.
4 g (yield 93.2%) was obtained.

[0052]

[Chemical formula 24]

2.40 g (0.0) of the compound obtained in ii)
1 mol), 30% H ₂ O ₂ 10 ml, acetic anhydride 8.3 g,
20 g of 99% formic acid and 3 ml of concentrated sulfuric acid were dissolved in 60 ml of CH ₂ Cl ₂ and stirred at 50 ° C. for 48 hours. The reaction solution was poured into water, extracted with CH ₂ Cl ₂ , and the organic layer was concentrated to obtain an ester. Next, the obtained ester form and 0.38 g (0.01 mol) of lithium aluminum hydride were added to an ether solution, and the mixture was stirred at 0 ° C. for 30 minutes. After carefully adding a small amount of water, the reaction solution was extracted from dilute hydrochloric acid with ether, and the extract was concentrated and purified by silica gel chromatography (developing solution: ethyl acetate / n-hexane = 10/90) to obtain the desired product 1. 30 g (yield 61.3%) was obtained.

¹ H-NMR (δ: CDCl ₃ ): 7.10 (d, 2
H), 6.75 (d, 2H), 4.70 (s, 1H), 2.55 (m, 1H), 2.30-1.60
(m, 8H)

[0055]

[Chemical 25]

0.40 g of the compound obtained in iii) (1.
89 mmol), 1.01 g (10 mmol) of triethylamine
Is dissolved in 10 ml of THF, 0.40 g (1.89 mmol) of 4-butoxybenzoic acid chloride is added, and the mixture is stirred at 80 ° C. for 1 hour. After concentrating the reaction solution, the residue was purified by silica gel chromatography (developing solution: chloroform),
0.55 g (yield 75%) of the desired product was obtained. ¹ H of target
-NMR is shown below.

¹ H-NMR (CDCl ₃ ): 8.15-6.95 (aromatic, 8H), 4.05 (t, 2H), 2.60 (m, 1H), 2.35-1.40 (m, 12)
H), 1.00 (t, 3H) Example 2

[0058]

[Chemical formula 26]

Compound 0.40 obtained in Example 1iii)
g (1.89 mmol), triethylamine 1.01 g (1
0 mmol) was dissolved in 10 ml of CH ₂ Cl ₂ and 0.39 g of trans-4-butylcyclohexylcarboxylic acid chloride was dissolved.
(1.89 mmol) is added and the mixture is reacted at room temperature for 2 hours. After concentrating the reaction solution, the residue was purified by silica gel chromatography (developing solution: chloroform) to obtain the desired product 0.69.
g (yield 96.7%) was obtained.

¹ H-NMR (CDCl ₃ ): 7.20 (d, 2H),
7.00 (d, 2H), 2.70-0.80 (m, 28H) Example 3

[0061]

[Chemical 27]

0.45 of the compound obtained in Example 1iii)
g (2.12 mmol), acyl bromide 1.10 g (1
0.6 mmol), potassium carbonate 1.47 g (10.6 mmo
l) is dissolved in 20 ml of acetone and refluxed overnight with stirring. After removing the inorganic substances by filtration, the filtrate was concentrated, and the residue was purified by silica gel chromatography (developing solution: n-hexane) to give 0.42 g of the desired product (yield 70.3%).
Got

¹ H-NMR (CDCl ₃ ): 7.15 (d, 2H),
6.80 (d, 2H), 3.95 (t, 2H), 2.55 (m, 1H), 2.30-0.90 (m, 17
H) Example 4

[0064]

[Chemical 28]

1.47 g of the compound obtained in Example 1ii)
(6.18 mmol) was dissolved in 60 ml of dioxane, and under ice cooling, 14.7 g (92 mmol) of bromine and 10.2 of NaOH.
30 ml of an aqueous solution of 1 g (255 mmol) are added dropwise. After the addition is complete, stir overnight at room temperature. The reaction solution was adjusted to pH = 1 with 17 g of sodium hydrogensulfate and then with concentrated hydrochloric acid, and then left overnight. The precipitated crystals were collected by filtration, washed with water, and dried well to obtain 1.32 g of the desired product (yield 89.0%).

[0066]

[Chemical 29]

0.60 g (2.5 m) of the compound obtained in i)
mol) is stirred with excess thionyl chloride for 1 hour at 80 ° C. and concentrated to give the acid chloride.

0.56 g of 4-octyloxyphenol
(2.5 mmol), 0.76 g of triethylamine (7.5
mmol) was dissolved in 20 ml of THF, the obtained acid chloride was added and reacted at 80 ° C. for 1 hour, the reaction solution was concentrated, and the residue was purified by silica gel chromatography (developing solution: chloroform) to obtain the desired product 0 0.78 g (yield 70.2
%) Was obtained.

¹ H-NMR (CDCl ₃ ): 8.15 (d, 2H),
7.85 (d, 2H), 7.10 (d, 2H), 6.90 (d, 2H), 3.95 (t, 2H), 2.7
0-0.80 (m, 24H)

[0070]

[Formulation Example] This compound is physically and chemically stable and exhibits a preferable liquid crystal phase (nematic phase) in a wide temperature range.
It can be used as an active ingredient of a liquid crystal composition. As a specific liquid crystal mixture to which the compound of the present invention can be added, for example, a mixture having a composition of A, B, C, D and E can be mentioned. In addition, a commercially available mixed liquid crystal ZLT-1565
(Merck Co., Ltd.) and the like are also included.

[0071]

[Chemical 30]

[0072]

[Chemical 31]

[0073]

[Test example]

[Test Example 1] [Measurement of physical properties] The phase transition temperature and phase of a compound were determined by visual observation with a polarizing microscope and a differential heat capacity meter (DSC). For Δn and Δε, refer to the literature method [Mitsuharu Okano and Shunsuke Kobayashi: Liquid Crystal-Basic Edition], Baifukan (198
5)] was measured.

[0074]

[Table 1]

Test Example 2 None of the following compounds described in JP-A-1-233239 shows nematic properties as a single product, and the addition amount to the liquid crystal mixture exhibiting nematic properties cannot be increased so much. On the other hand, the compound of the present invention shows nematic property as a single product, and therefore the addition amount is not limited.

Japanese Unexamined Patent Publication No. 1-233239 used in this test example
The compounds described in 1. are shown below.

[0077]

[Chemical 32]

[0078]

The compound of the present invention 4- (4-substituted aryl)
The -1,1-difluorohexane derivative is a novel compound and is provided as one component useful for preparing a liquid crystal composition used for a liquid crystal flat panel display or the like. That is, the compound is physically and chemically stable,
Preferably, it exhibits a stable liquid crystal phase (nematic liquid crystal phase),
Further, it has good compatibility with many other liquid crystal compounds such as ester-based, ether-based, carbonyl-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds, and is added to a liquid crystal composition containing them. It is possible to raise the NI point and improve other physical properties. As described above, the present invention provides a compound useful as one component in constructing a liquid crystal composition used in a liquid crystal flat panel display or the like. The present invention also provides a practical liquid crystal composition containing at least one compound of the present invention.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07C 67/10 67/293 67/343 69/75 B 9279-4H 69/753 D 9279-4H 69 / 757 C 9279-4H 69/76 A 9279-4H 69/773 9279-4H 69/92 9279-4H 323/62 7419-4H 327/24 7106-4H 327/26 7106-4H C07D 239/26 8615-4C 239/34 8615-4C 239/38 8615-4C C09K 19/30 9279-4H (72) Inventor Seiji Matsumoto 9 (72) Inventor Haruomi Honda, Kawanishi City Yamato, Hyogo Prefecture East 5-chome 56-6

Claims (6)

[Claims] 1. The formula: [In the formula, R is a linear or branched carbon atom having 1 to 1 carbon atoms.
0 represents an alkyl group, Q represents a single bond, an ether bond, a thioether bond, a carboxylic acid ester bond or a thiocarboxylic acid ester bond, and n represents 0, 1 or 2, and Z represents a single bond, a carboxylic ester bond, a thiocarboxylic ester bond, a methyleneoxy bond or an oxymethylene bond. However, when n is 0, at least one of Q and Z represents a single bond. ] The compound represented by these. 2. R is a linear alkyl group having 3 to 8 carbon atoms, and The compound according to claim 1, wherein n is 0 or 1, and Z is a single bond or a carboxylic acid ester bond. 3. A compound represented by the formula (I) is: The compound according to claim 1, which is 4. Formula (1): Or by condensing a compound represented by (2) The compound according to claim 1, which is obtained by condensing a compound represented by: 5. A formula (1): Or by reacting with a compound represented by the formula (2) [In the formula, Hal represents a halogen atom. ] And a compound of the formula: The method for producing a compound according to claim 1, which comprises reacting with a compound represented by: 6. A liquid crystal composition comprising the compound according to claim 1.