JPH061753A - Ester derivative - Google Patents
Ester derivativeInfo
- Publication number
- JPH061753A JPH061753A JP4214536A JP21453692A JPH061753A JP H061753 A JPH061753 A JP H061753A JP 4214536 A JP4214536 A JP 4214536A JP 21453692 A JP21453692 A JP 21453692A JP H061753 A JPH061753 A JP H061753A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- ester derivative
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 32
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004185 ester group Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 36
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000002140 halogenating effect Effects 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 150000002989 phenols Chemical class 0.000 abstract description 2
- YAEZTVSRAMOTPJ-UHFFFAOYSA-N (4-fluorophenyl) 2-fluorobenzoate Chemical compound C1=CC(F)=CC=C1OC(=O)C1=CC=CC=C1F YAEZTVSRAMOTPJ-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 238000000862 absorption spectrum Methods 0.000 description 18
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 17
- 239000000463 material Substances 0.000 description 10
- 238000010586 diagram Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000005711 Benzoic acid Substances 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 5
- BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- ORIRFPBZPCIUSA-UHFFFAOYSA-N (4-fluorophenyl) benzoate Chemical compound C1=CC(F)=CC=C1OC(=O)C1=CC=CC=C1 ORIRFPBZPCIUSA-UHFFFAOYSA-N 0.000 description 3
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 description 2
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 ester compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- PTSLQGSNQPTBCO-UHFFFAOYSA-N (3,4-difluorophenyl) 2,6-dichlorobenzoate Chemical compound C1=C(F)C(F)=CC=C1OC(=O)C1=C(Cl)C=CC=C1Cl PTSLQGSNQPTBCO-UHFFFAOYSA-N 0.000 description 1
- RZGRORAQOFLRLX-UHFFFAOYSA-N (3,4-difluorophenyl) 2,6-difluorobenzoate Chemical compound C1=C(F)C(F)=CC=C1OC(=O)C1=C(F)C=CC=C1F RZGRORAQOFLRLX-UHFFFAOYSA-N 0.000 description 1
- IJGSULQFKYOYEU-UHFFFAOYSA-N 2,3,4-trifluorophenol Chemical compound OC1=CC=C(F)C(F)=C1F IJGSULQFKYOYEU-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- ASEOANKNKCPMKP-UHFFFAOYSA-N C1=C(F)C(F)=CC=C1OC(=O)C1=CC=CC=C1F Chemical compound C1=C(F)C(F)=CC=C1OC(=O)C1=CC=CC=C1F ASEOANKNKCPMKP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000001630 Pyrus pyrifolia var culta Nutrition 0.000 description 1
- 240000002609 Pyrus pyrifolia var. culta Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は液晶材料として有用なエ
ステル誘導体、およびこのエステル誘導体を含有する液
晶組成物に関するものである。FIELD OF THE INVENTION The present invention relates to an ester derivative useful as a liquid crystal material, and a liquid crystal composition containing the ester derivative.
【０００２】[0002]
【従来の技術】液晶表示装置は、時計、電卓をはじめワ
ープロ、テレビ等に広く利用されている。これらの液晶
表示装置の中で特に多く使用されているのは、液晶材料
の光学的異方性および誘電異方性を利用したＴＮ型（ね
じれネマティック型）液晶表示装置である。2. Description of the Related Art Liquid crystal display devices are widely used in word processors, televisions, etc. as well as watches and calculators. Among these liquid crystal display devices, a TN type (twisted nematic type) liquid crystal display device that utilizes the optical anisotropy and the dielectric anisotropy of the liquid crystal material is particularly often used.
【０００３】[0003]
【発明が解決しようとする課題】現在ＴＮ型などの液晶
表示装置に用いられている液晶材料に要求される特性と
しては、液晶温度範囲が広いこと、電気光学的な応答速
度が速いこと、視野角範囲が広いこと、駆動電圧が低い
こと、化学的および光学的に安定であることなどが挙げ
られる。The liquid crystal materials currently used in liquid crystal display devices such as TN type are required to have a wide liquid crystal temperature range, a high electro-optical response speed, and a visual field. It has a wide angular range, a low driving voltage, and is chemically and optically stable.
【０００４】高視野角、高コントラストを得るために
は、液晶層のリターデーション△ｎ・ｄ（△ｎは液晶材
料の複屈折、ｄは液晶層の厚み）を最適化する必要があ
る。しかし、実用に使用される液晶表示装置では液晶層
の厚みがある限定された範囲で設定されているため、液
晶材料のΔｎの最適化が必要となっていた。In order to obtain a wide viewing angle and a high contrast, it is necessary to optimize the retardation Δn · d (Δn is the birefringence of the liquid crystal material, d is the thickness of the liquid crystal layer) of the liquid crystal layer. However, in a practically used liquid crystal display device, since the thickness of the liquid crystal layer is set within a limited range, it is necessary to optimize Δn of the liquid crystal material.
【０００５】また、高速化のためには液晶材料に低粘性
が望まれる。電圧印加時の立ち上がり時間τonと電圧遮
断時の立ち下がり時間τoff はτon＝ηiiｄ2 （ε0 Δ
εＶ2 −Ｋπ2 ）- 1τoff ＝ηiiｄ2 ／π2 Ｋで与え
られる。ここで、ηiiは粘性のパラメータ、ｄは液晶層
の厚み、ε0 は真空中の誘電率、Δεは誘電率の異方
性、Ｖは印加電圧、Ｋ＝Ｋ11＋（Ｋ33−２Ｋ22）／４で
ある。よって、応答速度をより速くするためには液晶材
料が低粘性であること、つまり低粘性の液晶化合物が不
可欠となっていた。Further, in order to increase the speed, it is desired that the liquid crystal material has low viscosity. The rise time τon when voltage is applied and the fall time τoff when voltage is cut off are τon = ηiid 2 (ε0 Δ
εV 2 -Kπ 2) - it is given by 1 τoff = ηiid 2 / π 2 K. Where ηii is the viscosity parameter, d is the thickness of the liquid crystal layer, ε0 is the dielectric constant in vacuum, Δε is the anisotropy of the dielectric constant, V is the applied voltage, and K = K11 + (K33-2K22) / 4. . Therefore, a liquid crystal material having a low viscosity, that is, a low-viscosity liquid crystal compound is indispensable in order to increase the response speed.
【０００６】さらに駆動電圧はしきい値電圧Ｖthの値に
依存し、しきい値電圧Ｖthを小さくすることにより、よ
り低い電圧で液晶表示装置を駆動させることができる。
よって、しきい値電圧Ｖthを小さくする液晶材料が必要
となっていた。Further, the driving voltage depends on the value of the threshold voltage Vth, and by lowering the threshold voltage Vth, the liquid crystal display device can be driven at a lower voltage.
Therefore, a liquid crystal material that reduces the threshold voltage Vth has been required.
【０００７】以上のような特性を全て満足する単一の液
晶化合物は未だに見い出されていない。そのためにいろ
いろな特性をもった数種の液晶化合物を混合したり、あ
るいは非液晶化合物を混合したりして実用に供している
のが現状である。A single liquid crystal compound satisfying all the above characteristics has not yet been found. Therefore, at present, several kinds of liquid crystal compounds having various characteristics are mixed or non-liquid crystal compounds are mixed for practical use.
【０００８】そこで本発明の目的は、液晶組成物に混合
することによって、液晶組成物のΔｎの値を最適化し、
粘度を低下させ、しきい値電圧Ｖthを小さくすることの
できるエステル誘導体を提供することである。Therefore, an object of the present invention is to optimize the value of Δn of the liquid crystal composition by mixing with the liquid crystal composition,
An object of the present invention is to provide an ester derivative that can reduce the viscosity and the threshold voltage Vth.
【０００９】[0009]
【課題を解決するための手段】本発明のエステル誘導体
は一般式（Ｉ）で表されるものである。Means for Solving the Problems The ester derivative of the present invention is represented by the general formula (I).
【００１０】[0010]
【化２】 [Chemical 2]
【００１１】（ただし、Ｖ、Ｗ、Ｘ、Ｙ、およびＺはそ
れぞれ水素原子またはハロゲン原子を示す。）(However, V, W, X, Y, and Z each represent a hydrogen atom or a halogen atom.)
【００１２】また、本発明の液晶組成物は、一般式
（Ｉ）で表されるエステル誘導体を少なくとも一種含有
するものである。The liquid crystal composition of the present invention contains at least one ester derivative represented by the general formula (I).
【００１３】ハロゲン原子としては、Ｆ、Ｃｌ、Ｂｒが
挙げられる。Examples of the halogen atom include F, Cl and Br.
【００１４】本発明のエステル誘導体の製造方法につい
て説明する。化３はその一例を示したものである。まず
カルボン酸（ａ）に塩化チオニル、五酸化リン等のハロ
ゲン化剤を作用させて酸塩化物（ｂ）を製造する。次に
酸塩化物（ｂ）と置換フェノール（ｃ）とをピリジン等
の不活性有機溶媒中で反応させた後、反応混合物を水
洗、乾燥、再結晶することにより一般式（Ｉ）で表され
るエステル誘導体を得ることができる。The method for producing the ester derivative of the present invention will be described. Chemical formula 3 shows an example thereof. First, a carboxylic acid (a) is treated with a halogenating agent such as thionyl chloride or phosphorus pentoxide to produce an acid chloride (b). Next, the acid chloride (b) and the substituted phenol (c) are reacted in an inert organic solvent such as pyridine, and then the reaction mixture is washed with water, dried and recrystallized to obtain the compound represented by the general formula (I). Ester derivative can be obtained.
【００１５】[0015]
【化３】 [Chemical 3]
【００１６】本発明のエステル誘導体は多くの液晶化合
物と混合し液晶組成物を製造することができる。本発明
のエステル誘導体と混合可能な液晶化合物としてはエス
テル系、シクロヘキシルフェニル系、ビフェニル系、ピ
リミジン系、ジオキサン系、トラン系などが挙げられ
る。The ester derivative of the present invention can be mixed with many liquid crystal compounds to produce a liquid crystal composition. Examples of the liquid crystal compound that can be mixed with the ester derivative of the present invention include ester compounds, cyclohexylphenyl compounds, biphenyl compounds, pyrimidine compounds, dioxane compounds, and tolan compounds.
【００１７】[0017]
【実施例】実施例を用いて本発明を具体的に説明する
が、本発明はこれら実施例に限定されるものではない。EXAMPLES The present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
【００１８】（実施例１）安息香酸１２．２ｇに塩化チ
オニル２４ｇを加え、還流下で２時間反応させ、反応終
了後減圧下で塩化チオニルを留去し、その後２０ｍｍＨ
ｇで減圧蒸留し、留出温度１０５℃で安息香酸酸塩化物
１０ｇを得た。これをトルエン５０ｍｌに溶解し、４−
フロロフェノール８ｇとピリジン８ｇを加え４０℃で３
時間反応させた。反応終了後１００ｍｌの水を加えて有
機層を分離し、希塩酸次いで希アルカリ水溶液の順で洗
浄し、さらに飽和食塩水で洗浄した後、無水硫酸ナトリ
ウムを加えて乾燥させた。次にこの有機層を濾過し、濾
液から溶媒を減圧留去した。得られた反応生成物をヘキ
サンから再結晶し、１ｍｍＨｇで減圧蒸留を行い（留出
温度１６０℃）、化４で表される安息香酸−（４−フロ
ロフェニル）エステル９ｇを得た。この化合物は融点５
８．０℃であった。また、この化合物の赤外線吸光スペ
クトルを図１に示す。(Example 1) 24 g of thionyl chloride was added to 12.2 g of benzoic acid and reacted for 2 hours under reflux. After completion of the reaction, thionyl chloride was distilled off under reduced pressure and then 20 mmH.
Distillation under reduced pressure was performed at a distillation temperature of 105 ° C. to obtain 10 g of benzoic acid chloride. Dissolve this in 50 ml of toluene,
Add 8 g of fluorophenol and 8 g of pyridine, and add 3 at 40 ° C.
Reacted for hours. After the completion of the reaction, 100 ml of water was added to separate the organic layer, which was washed with dilute hydrochloric acid and then with a dilute alkaline aqueous solution in that order, further washed with saturated saline, and then dried with anhydrous sodium sulfate. Next, this organic layer was filtered, and the solvent was distilled off from the filtrate under reduced pressure. The obtained reaction product was recrystallized from hexane and distilled under reduced pressure at 1 mmHg (distillation temperature 160 ° C.) to obtain 9 g of benzoic acid- (4-fluorophenyl) ester represented by Chemical formula 4. This compound has a melting point of 5
It was 8.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００１９】[0019]
【化４】 [Chemical 4]
【００２０】（実施例２）安息香酸１２．２ｇの代わり
に２−フロロ安息香酸１４．６ｇを使用する以外は実施
例１と同様の方法で化５で表される２−フロロ安息香酸
−（４−フロロフェニル）エステル１０ｇを得た。この
化合物は融点４０．８℃、沸点１５０℃（１ｍｍＨｇ）
であった。また、この化合物の赤外線吸収スペクトルを
図２に示す。(Example 2) 2-Fluorobenzoic acid-(-) represented by Chemical formula 5 in the same manner as in Example 1 except that 14.6 g of 2-fluorobenzoic acid was used instead of 12.2 g of benzoic acid. 10 g of 4-fluorophenyl) ester was obtained. This compound has a melting point of 40.8 ° C and a boiling point of 150 ° C (1 mmHg)
Met. The infrared absorption spectrum of this compound is shown in FIG.
【００２１】[0021]
【化５】 [Chemical 5]
【００２２】（実施例３）安息香酸１２．２ｇの代わり
に２，６−ジフロロ安息香酸１６．２ｇを使用する以外
は実施例１と同様の方法で化６で表される２，６−ジフ
ロロ安息香酸−（４−フロロフェニル）エステル１１ｇ
を得た。この化合物は融点６０．０℃であった。また、
この化合物の赤外線吸収スペクトルを図３に示す。(Example 3) 2,6-difluoro represented by Chemical formula 6 was prepared in the same manner as in Example 1 except that 16.2 g of 2,6-difluorobenzoic acid was used instead of 12.2 g of benzoic acid. Benzoic acid- (4-fluorophenyl) ester 11 g
Got This compound had a melting point of 60.0 ° C. Also,
The infrared absorption spectrum of this compound is shown in FIG.
【００２３】[0023]
【化６】 [Chemical 6]
【００２４】（実施例４）安息香酸１２．２ｇの代わり
に２，６−ジクロロ安息香酸１９．５ｇを使用する以外
は実施例１と同様の方法で化７で表される２，６−ジク
ロロ安息香酸−（４−フロロフェニル）エステル１２ｇ
を得た。この化合物は融点８６．０℃であった。また、
この化合物の赤外線吸収スペクトルを図４に示す。(Example 4) 2,6-dichloro represented by Chemical formula 7 was prepared in the same manner as in Example 1 except that 19.5 g of 2,6-dichlorobenzoic acid was used instead of 12.2 g of benzoic acid. Benzoic acid- (4-fluorophenyl) ester 12 g
Got This compound had a melting point of 86.0 ° C. Also,
The infrared absorption spectrum of this compound is shown in FIG.
【００２５】[0025]
【化７】 [Chemical 7]
【００２６】（実施例５）４−フロロフェノール８ｇの
代わりに３，４−ジフロロフェノール９．５ｇを使用す
る以外は実施例１と同様の方法で化８で表される安息香
酸−（３，４−ジフロロフェニル）エステル９ｇを得
た。この化合物は融点７４．０℃であった。また、この
化合物の赤外線吸収スペクトルを図５に示す。Example 5 The benzoic acid- (3 represented by Chemical formula 8 was prepared in the same manner as in Example 1 except that 9.5 g of 3,4-difluorophenol was used instead of 8 g of 4-fluorophenol. , 4-difluorophenyl) ester was obtained. This compound had a melting point of 74.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００２７】[0027]
【化８】 [Chemical 8]
【００２８】（実施例６）安息香酸１２．２ｇの代わり
に２−フロロ安息香酸１４．６ｇを、４−フロロフェノ
ール８ｇの代わりに３，４−ジフロロフェノール９．５
ｇを使用する以外は実施例１と同様の方法で化９で表さ
れる２−フロロ安息香酸−（３，４−ジフロロフェニ
ル）エステル１０ｇを得た。この化合物は融点６５．１
℃であった。また、この化合物の赤外線吸収スペクトル
を図６に示す。(Example 6) 14.6 g of 2-fluorobenzoic acid was used instead of 12.2 g of benzoic acid, and 9.5 of 3,4-difluorophenol was used instead of 8 g of 4-fluorophenol.
10 g of 2-fluorobenzoic acid- (3,4-difluorophenyl) ester represented by Chemical formula 9 was obtained in the same manner as in Example 1 except that g was used. This compound has a melting point of 65.1.
It was ℃. The infrared absorption spectrum of this compound is shown in FIG.
【００２９】[0029]
【化９】 [Chemical 9]
【００３０】（実施例７）安息香酸１２．２ｇの代わり
に２，６−ジフロロ安息香酸１６．２ｇを、４−フロロ
フェノール８ｇの代わりに３，４−ジフロロフェノール
９．５ｇを使用する以外は実施例１と同様の方法で化１
０で表される２，６−ジフロロ安息香酸−（３，４−ジ
フロロフェニル）エステル１１ｇを得た。この化合物は
融点７８．０℃であった。また、この化合物の赤外線吸
収スペクトルを図７に示す。Example 7 Except that 16.2 g of 2,6-difluorobenzoic acid was used instead of 12.2 g of benzoic acid and 9.5 g of 3,4-difluorophenol was used instead of 8 g of 4-fluorophenol. In the same manner as in Example 1
11 g of 2,6-difluorobenzoic acid- (3,4-difluorophenyl) ester represented by 0 was obtained. This compound had a melting point of 78.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００３１】[0031]
【化１０】 [Chemical 10]
【００３２】（実施例８）安息香酸１２．２ｇの代わり
に２，６−ジクロロ安息香酸１９．５ｇを、４−フロロ
フェノール８ｇの代わりに３，４−ジフロロフェノール
９．５ｇを使用する以外は実施例１と同様の方法で化１
１で表される２，６−ジクロロ安息香酸−（３，４−ジ
フロロフェニル）エステル１２ｇを得た。この化合物は
融点８６．０℃であった。また、この化合物の赤外線吸
収スペクトルを図８に示す。Example 8 19.5 g of 2,6-dichlorobenzoic acid was used instead of 12.2 g of benzoic acid, and 9.5 g of 3,4-difluorophenol was used instead of 8 g of 4-fluorophenol. In the same manner as in Example 1
12 g of 2,6-dichlorobenzoic acid- (3,4-difluorophenyl) ester represented by 1 was obtained. This compound had a melting point of 86.0 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００３３】[0033]
【化１１】 [Chemical 11]
【００３４】（実施例９）安息香酸１２．２ｇの代わり
に２−フロロ安息香酸１４．６ｇを、４−フロロフェノ
ール８ｇの代わりに２，３，４−トリフロロフェノール
１０．５ｇを使用する以外は、実施例１と同様の方法で
化１２で表される２−フロロ安息香酸−（２，３，４−
トリフロロフェニル）エステル１１ｇを得た。この化合
物は、融点５０．３℃であった。また、この化合物の赤
外線吸収スペクトルを図９に示す。Example 9 14.6 g of 2-fluorobenzoic acid was used instead of 12.2 g of benzoic acid, and 10.5 g of 2,3,4-trifluorophenol was used instead of 8 g of 4-fluorophenol. Is 2-fluorobenzoic acid- (2,3,4-represented by Chemical formula 12 in the same manner as in Example 1.
11 g of trifluorophenyl) ester was obtained. This compound had a melting point of 50.3 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【００３５】[0035]
【化１２】 [Chemical 12]
【００３６】（実施例１０）化１３で表される化合物を
混合した液晶組成物９０重量部に、実施例１で製造した
本発明のエステル誘導体を１０重量部加え液晶組成物を
作製した。その液晶組成物の特性を表１に示す。なお、
表中しきい値電圧Ｖthはこの液晶組成物をセル厚９μｍ
のＴＮ型液晶表示装置に搭載した際の値である。ここ
で、化１３で表される化合物のみからなる液晶組成物の
特性はＮ−Ｉ点７２℃、Δｎ０．１３８、粘度２７．９
ｃｐ、Ｖth１．６８Ｖであった。Example 10 A liquid crystal composition was prepared by adding 10 parts by weight of the ester derivative of the present invention prepared in Example 1 to 90 parts by weight of the liquid crystal composition mixed with the compound represented by Chemical formula 13. The characteristics of the liquid crystal composition are shown in Table 1. In addition,
The threshold voltage Vth in the table is obtained by using this liquid crystal composition in a cell thickness of 9 μm.
It is a value when mounted on the TN type liquid crystal display device. Here, the liquid crystal composition consisting of the compound represented by Chemical formula 13 has the following characteristics: NI point 72 ° C., Δn 0.138, viscosity 27.9.
It was cp and Vth 1.68V.
【００３７】[0037]
【化１３】 [Chemical 13]
【００３８】[0038]
【表１】 [Table 1]
【００３９】（実施例１１〜１６）実施例１０と同様に
化１３で表される化合物を混合した液晶組成物９０重量
部に、実施例２、３、５、６、７、９で製造したエステ
ル誘導体をそれぞれ１０重量部ずつ加え、液晶組成物を
作製した。その液晶組成物の特性を表１に示す。(Examples 11 to 16) 90 parts by weight of a liquid crystal composition prepared by mixing the compound represented by Chemical formula 13 in the same manner as in Example 10 was prepared in Examples 2, 3, 5, 6, 7, and 9. A liquid crystal composition was prepared by adding 10 parts by weight of each ester derivative. The characteristics of the liquid crystal composition are shown in Table 1.
【００４０】表１から明らかなように、本発明のエステ
ル誘導体はその添加により液晶組成物のΔｎを最適化
し、しきい値電圧Ｖthを下げるものである。また、ほと
んどの場合粘度を低下させることもできる。As is clear from Table 1, the addition of the ester derivative of the present invention optimizes Δn of the liquid crystal composition and lowers the threshold voltage Vth. In most cases, the viscosity can be reduced.
【００４１】[0041]
【発明の効果】本発明のエステル誘導体は、液晶組成物
に混合することによって、液晶組成物のΔｎを最適化
し、しきい値電圧Ｖthを小さくすることができ、また粘
度を低下させることもできる。そのため本発明のエステ
ル誘導体を含有する液晶組成物は液晶材料として優れた
特性を有し、またこの液晶組成物を搭載した液晶表示装
置は良好な表示特性を有する。さらに、本発明のエステ
ル誘導体は種々の化合物との相互溶解性が大きく、液晶
組成物の構成物質として多くの液晶材料と組み合わせて
使用することができ、液晶組成物の特性改良に有用なも
のである。By mixing the ester derivative of the present invention in a liquid crystal composition, the Δn of the liquid crystal composition can be optimized, the threshold voltage Vth can be reduced, and the viscosity can be lowered. . Therefore, a liquid crystal composition containing the ester derivative of the present invention has excellent properties as a liquid crystal material, and a liquid crystal display device equipped with this liquid crystal composition has good display properties. Furthermore, the ester derivative of the present invention has a high mutual solubility with various compounds, can be used in combination with many liquid crystal materials as a constituent of a liquid crystal composition, and is useful for improving the characteristics of the liquid crystal composition. is there.
【図１】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of an ester derivative of the present invention.
【図２】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 2 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図３】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 3 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図４】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 4 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図５】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 5 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図６】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 6 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図７】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 7 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図８】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 8 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
【図９】本発明のエステル誘導体の赤外線吸収スペクト
ルを表す図である。FIG. 9 is a diagram showing an infrared absorption spectrum of the ester derivative of the present invention.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 行成 俊郎 山梨県南都留郡河口湖町船津6663番地の２ 河口湖精密株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Toshiro Yukinari 2666-3 Funatsu, Kawaguchiko Town, Minamitsuru District, Yamanashi Prefecture Kawaguchiko Precision Co., Ltd.
Claims (2)
体。 【化１】 （ただし、Ｖ、Ｗ、Ｘ、Ｙ、およびＺはそれぞれ水素原
子またはハロゲン原子を示す。）1. An ester derivative represented by the general formula (I). [Chemical 1] (However, V, W, X, Y, and Z each represent a hydrogen atom or a halogen atom.)
とも一種含有する液晶組成物。2. A liquid crystal composition containing at least one ester derivative according to claim 1.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21453692A JP3268836B2 (en) | 1992-04-22 | 1992-07-20 | Liquid crystal composition containing ester derivative |
| DE69311011T DE69311011T2 (en) | 1992-07-20 | 1993-07-20 | 4-fluorophenyl benzoates and liquid crystalline compositions containing them |
| US08/094,569 US5364558A (en) | 1992-07-20 | 1993-07-20 | Ester derivatives |
| KR1019930013629A KR940005543A (en) | 1992-07-20 | 1993-07-20 | Ester derivatives |
| EP93111595A EP0580122B1 (en) | 1992-07-20 | 1993-07-20 | 4-Fluorophenylbenzoates and liquid crystal compositions containing them |
| HK98100629A HK1001688A1 (en) | 1992-07-20 | 1998-01-23 | 4-Fluorophenylbenzoates and liquid crystal compositions containing them |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12801292 | 1992-04-22 | ||
| JP4-128012 | 1992-04-22 | ||
| JP21453692A JP3268836B2 (en) | 1992-04-22 | 1992-07-20 | Liquid crystal composition containing ester derivative |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001180949A Division JP3636676B2 (en) | 1992-04-22 | 2001-06-15 | Ester derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH061753A true JPH061753A (en) | 1994-01-11 |
| JP3268836B2 JP3268836B2 (en) | 2002-03-25 |
Family
ID=26463810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21453692A Expired - Fee Related JP3268836B2 (en) | 1992-04-22 | 1992-07-20 | Liquid crystal composition containing ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3268836B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8443830B2 (en) | 2007-04-02 | 2013-05-21 | Fujikin Incorporated | Heater built-in valve |
-
1992
- 1992-07-20 JP JP21453692A patent/JP3268836B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8443830B2 (en) | 2007-04-02 | 2013-05-21 | Fujikin Incorporated | Heater built-in valve |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3268836B2 (en) | 2002-03-25 |
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