JP3579912B2 - Benzene derivative and liquid crystal composition - Google Patents

Description

【０００７】
（式中、Ｒ^１ はアルキル基、アルコキシ基、アルコキシアルキル基、アルコキシアルコキシ基、パーフルオロアルキルアルコキシ基、ハロゲン原子、トリフルオロメチル基、トリフルオロメトキシ基、シアノ基、ニトロ基を示し、Ｒ^２ は水素原子、アルキル基、アルコキシ基、アルコキシアルキル基、アルコキシアルコキシ基、パーフルオロアルキルアルコキシ基、ハロゲン原子、トリフルオロメチル基、トリフルオロメトキシ基、シアノ基、ニトロ基を示しｍは１又は２を示し、Ｒｆは−Ｃ_ｎ Ｆ_２ｎ＋１または−Ｃ_ｎ Ｆ_２ｎＨを示し、ｎは１〜１８を示す。）で表わされるベンゼン誘導体に存する。
【０００８】
式〔Ｉ〕においてＲ^１ は、メチル基、エチル基、プロピル基、ブチル基、ヘキシル基、オクチル基、デシル基などのＣ_１ 〜Ｃ_１８のアルキル基、メトキシ基、エトキシ基、ブトキシ基、オクチルオキシ基、デシルオキシ基などのＣ_１ 〜Ｃ_１８のアルコキシ基、メトキシメチル基、エトキシエチル基、ブトキシエチル基などのアルコキシアルキル基、メトキシメトキシ基、エトキシエトキシ基、ブトキシエトキシ基などのアルコキシアルコキシ基、パーフルオロエチルメトキシ基、パーフルオロブチルエトキシ基、パーフルオロヘキシルエトキシ基などのフルオロアルキル置換アルコキシ基、フッ素原子、塩素原子、臭素原子などのハロゲン原子、トリフルオロメチル基、トリフルオロメトキシ基、シアノ基、ニトロ基が挙げられ、アルキル基、アルコキシ基、ハロゲン原子、ニトロ基が好ましい。
【０００９】
Ｒ^２ は水素原子又は上記Ｒ^１ と同じ基が挙げられ、水素原子、アルキル基、アルコキシ基、ハロゲン原子、ニトロ基が好ましく、水素原子、アルコキシ基が特に好ましい。
Ｒｆは−Ｃ_ｎ Ｆ_２ｎ＋１または−Ｃ_ｎ Ｆ_２ｎＨが挙げられ、−Ｃ_ｎ Ｆ_２ｎ＋１が好ましい。
【００１０】
ｍは１又２、ｎは１〜１８、好ましくは４〜１０、特に好ましくは６〜８の数を示す。
本発明の前記一般式〔Ｉ〕の化合物は下記の一般式〔ＩＩ〕
【００１１】
【化３】

【００１２】
（式中、Ｒ^１ 及びＲ^２ は一般式〔Ｉ〕におけると同一の意義を有する）で示される安息香酸誘導体と下記の一般式〔ＩＩＩ 〕
【００１３】
【化４】
ＨＯ−（ＣＨ_２ ）_ｍ ・Ｒｆ 〔ＩＩＩ 〕
【００１４】
（式中、ｍ，Ｒｆは一般式〔Ｉ〕におけると同一の意義を有する）で示されるアルコール誘導体を公知の方法で反応させることにより製造することができる。
本発明のベンゼン誘導体は、日本学術振興会第１４２委員会編“液晶デバイスハンドブック”Ｐ１０７〜１９２（日刊工業新聞社）などに記載されている、ビフェニル系、フェニルシクロヘキサン系、シクロヘキシルカルボン酸フェニルエステル系、フェニルピリミジン系などの各種の液晶物質と公知の方法で混合することにより、液晶組成物を調整することができる。
【００１５】
本発明の液晶組成物には、コレステリルノナノエートなどの光学活性物質、紫外線吸収剤、酸化防止剤、二色性色素などの各種の添加剤を加えることができる。
本発明の液晶組成物を用いて、日本学術振興会第１４２委員会編“液晶デバイスハンドブック”Ｐ３０３〜３８６（日刊工業新聞社）などに記載されている各種の表示素子を構成することができる。
【００１６】
【発明の効果】
本発明の新規な単環性液晶性化合物およびこれらを用いた液晶組成物によって、低コストなどの実用性や性能の優れた液晶表示を実現することができる。
【００１７】
【実施例】
次に、本発明を実施例により具体的に説明するが、本発明はこれら実施例により何ら限定されるものではない。
実施例１
２−メチル−４−ヘキシルオキシ安息香酸２．０ｇと五塩化リン１．４ｇを７０℃で３０分加熱後、減圧下にオキシ塩化リンを除去して、２−メチル−４−ヘキシルオキシ安息香酸クロリドを得た。これをトルエン３０ｍｌに溶解した溶液に、２−パーフルオロヘキシルエタノール３．１ｇをピリジン３０ｍｌに溶解した溶液を滴下した後、撹拌下９０℃で８時間加熱反応させた。反応後、減圧下に溶媒を留去した後、生成物をシリカゲルを用いたカラムクロマトにより精製して前記一般式〔Ｉ〕においてＲ^１ がメチル基、Ｒ^２ はヘキシルオキシ基、ｍが２、ＲｆがＣ_６ Ｆ_１３で示される油状の目的物、２−メチル−４−ヘキシルオキシ安息香酸−２′−パーフルオロヘキシルエチルエステルを得た。本化合物は下記の表−Ｉの実施例２−７に示すように融点１４℃を有していた。表中、Ｉは等方相、Ｓ_１ 、Ｓ_２ は各々異なるスメクティク相、Ｃは結晶相を、括弧内はモノトロピック液晶領域を示す。
【００１８】
実施例２
実施例１に準じた方法により、表−Ｉに示す化合物を得た。
【００１９】
【表１】

[0001]
[Industrial applications]
The present invention relates to a liquid crystal material and a liquid crystal composition used for a display element and the like.
[0002]
[Prior art]
Conventionally, as liquid crystal materials used for liquid crystal display and the like, biphenyl, phenylcyclohexane, and the like can be found in “Liquid Crystal Device Handbook”, pages 107 to 192 (Nikkan Kogyo Shimbun), edited by the 142nd Committee of the Japan Society for the Promotion of Science. In addition to a so-called bicyclic liquid crystal substance having a skeleton of cyclohexylcarboxylic acid phenyl ester, cyclohexylcyclohexane, phenylpyrimidine, or fetyl dioxane, a tricyclic liquid crystal substance having a skeleton of cyclohexylbiphenyl or the like, and a skeleton of cyclohexylbiphenylcyclohexane or the like. However, monocyclic liquid crystal substances are extremely rare, and no highly practical monocyclic liquid crystal substances have been known.
[0003]
In the case of a liquid crystal composition, a method of adjusting the liquid crystal temperature range or the like by generally using the above-mentioned bicyclic liquid crystal substance as a main component and adding a tricyclic or tetracyclic liquid crystal substance thereto has been generally performed. .
However, these bicyclic, tricyclic and tetracyclic liquid crystal materials have a disadvantage that the manufacturing process is generally complicated as the number of rings increases, and the cost is liable to increase significantly.
[0004]
[Problems to be solved by the invention]
An object of the present invention is to provide a novel and highly practical monocyclic liquid crystal material useful for solving these problems and a liquid crystal composition using the same.
[0005]
[Means for Solving the Problems]
The gist of the present invention is the following general formula [I]
[0006]
Embedded image

[0007]
(Wherein, R ¹ represents an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, perfluoroalkyl alkoxy group, a halogen atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a nitro group, R ² Represents a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a perfluoroalkylalkoxy group, a halogen atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, or a nitro group, and m represents 1 or 2. shows, Rf represents a _-C n _{F 2n + 1} or _-C n _{F 2n} H, n consists in benzene derivative represented by indicating from 1 to 18.).
[0008]
In the formula [I], R ¹ represents a C _{1 to} C ₁₈ alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group, a decyl group, a methoxy group, an ethoxy group, a butoxy group, an octyl group. An oxy group, a C _{1 to} C ₁₈ alkoxy group such as a decyloxy group, an alkoxyalkyl group such as a methoxymethyl group, an ethoxyethyl group, a butoxyethyl group, an alkoxyalkoxy group such as a methoxymethoxy group, an ethoxyethoxy group, and a butoxyethoxy group; Fluoroalkyl-substituted alkoxy groups such as perfluoroethylmethoxy group, perfluorobutylethoxy group, perfluorohexylethoxy group, halogen atoms such as fluorine atom, chlorine atom, and bromine atom, trifluoromethyl group, trifluoromethoxy group, and cyano group , Nitro groups, and alkyl Preferred are an alkyl group, an alkoxy group, a halogen atom and a nitro group.
[0009]
R ² is a hydrogen atom or the same group as R ¹ described above, preferably a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a nitro group, particularly preferably a hydrogen atom or an alkoxy group.
Rf is _-C n _{F 2n + 1} or _-C n _{F 2n} H can be _mentioned, -C _{n F 2n + 1} is preferred.
[0010]
m represents 1 or 2, n represents 1 to 18, preferably 4 to 10, particularly preferably 6 to 8.
The compound of the general formula [I] of the present invention has the following general formula [II]
[0011]
Embedded image

[0012]
(Wherein R ¹ and R ² have the same meaning as in the general formula [I]) and the following general formula [III]
[0013]
Embedded image
HO- _{(CH 2)} m · Rf (III)
[0014]
(Wherein m and Rf have the same meanings as in the general formula [I]), and can be produced by reacting the alcohol derivative by a known method.
The benzene derivative of the present invention is a biphenyl type, a phenylcyclohexane type, or a cyclohexylcarboxylic acid phenyl ester type described in “Liquid Crystal Device Handbook”, pages 107 to 192 (Nikkan Kogyo Shimbun), edited by the 142nd Committee of the Japan Society for the Promotion of Science. The liquid crystal composition can be adjusted by mixing with various liquid crystal substances such as phenylpyrimidine and the like by a known method.
[0015]
Various additives such as an optically active substance such as cholesteryl nonanoate, an ultraviolet absorber, an antioxidant, and a dichroic dye can be added to the liquid crystal composition of the present invention.
Using the liquid crystal composition of the present invention, various display elements described in “Liquid Crystal Device Handbook”, pages 303 to 386 (Nikkan Kogyo Shimbun), edited by the 142nd Committee of the Japan Society for the Promotion of Science can be constructed.
[0016]
【The invention's effect】
The novel monocyclic liquid crystalline compound of the present invention and a liquid crystal composition using the same can realize a liquid crystal display excellent in practicality and performance such as low cost.
[0017]
【Example】
Next, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
Example 1
After heating 2.0 g of 2-methyl-4-hexyloxybenzoic acid and 1.4 g of phosphorus pentachloride at 70 ° C. for 30 minutes, phosphorus oxychloride was removed under reduced pressure to give 2-methyl-4-hexyloxybenzoic acid. Chloride was obtained. A solution in which 3.1 g of 2-perfluorohexylethanol was dissolved in 30 ml of pyridine was added dropwise to a solution of this in 30 ml of toluene, and the mixture was heated and reacted at 90 ° C. for 8 hours with stirring. After the reaction, the solvent was distilled off under reduced pressure, and the product was purified by column chromatography using silica gel. In the general formula [I], R ¹ was a methyl group, R ² was a hexyloxy group, m was 2, Rf is the desired product as an oil represented by _C 6 _{F 13,} to give 2-methyl-4-hexyloxy benzoic acid-2'-perfluorohexyl ethyl ester. This compound had a melting point of 14 ° C. as shown in Example 2-7 of Table I below. In the table, I indicates an isotropic phase, S ₁ and S ₂ indicate different smectic phases, C indicates a crystal phase, and parentheses indicate a monotropic liquid crystal region.
[0018]
Example 2
By the method according to Example 1, the compounds shown in Table-I were obtained.
[0019]
[Table 1]

Claims (2)

The following general formula [I]

(Wherein, R ¹ represents an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, perfluoroalkyl alkoxy group, a halogen atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a nitro group, R ² Represents a hydrogen atom, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a perfluoroalkylalkoxy group, a halogen atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, or a nitro group, and m is 1 or 2 are shown, Rf represents a -C _n F _{2n + 1} or -C _n F _2n H, _n is a liquid crystal composition characterized by containing a benzene-induced body represented by indicating from 1 to 18.). In the general formula [I], R ^One Is an alkyl group, an alkoxy group, a halogen atom or a nitro group; ^Two Is a hydrogen atom or an alkoxy group; f Is -C _n F _{2n + 1} The liquid crystal composition according to claim 1, wherein