JPS59155338A - Ester derivative of 2,6-difluorobenzoic acid - Google Patents
Ester derivative of 2,6-difluorobenzoic acidInfo
- Publication number
- JPS59155338A JPS59155338A JP2898883A JP2898883A JPS59155338A JP S59155338 A JPS59155338 A JP S59155338A JP 2898883 A JP2898883 A JP 2898883A JP 2898883 A JP2898883 A JP 2898883A JP S59155338 A JPS59155338 A JP S59155338A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- trans
- liquid crystal
- compound
- difluorobenzoic acid
- 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.)
- Pending
Links
- -1 Ester derivative of 2,6-difluorobenzoic acid Chemical class 0.000 title claims description 7
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005611 electricity Effects 0.000 abstract description 2
- ONOTYLMNTZNAQZ-UHFFFAOYSA-N 2,6-difluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=CC=C1F ONOTYLMNTZNAQZ-UHFFFAOYSA-N 0.000 abstract 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KKTYQZBIEAZLEC-UHFFFAOYSA-N 4-(4-benzylphenyl)benzonitrile Chemical group N#Cc1ccc(cc1)-c1ccc(Cc2ccccc2)cc1 KKTYQZBIEAZLEC-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は液晶組成物の成分として有用な、新規な含フツ
素有機化合物及びそれを含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel fluorine-containing organic compound useful as a component of a liquid crystal composition and a liquid crystal composition containing the same.
液晶を応用した表示素子は時計、電車などに広く使用さ
れる様になって来た。この液晶表示素子は液晶物質の光
学異方性及び誘電異方性という性質を利用したものであ
るが、液晶相にはネマチック液晶相、スメクチック液晶
相、コレステリック液晶相があシ、そのうちネマチック
液晶を利用したものが最も広く実用化されている。即ち
それらにはＴＮ（ねじれネマチック）型、ＤＳ型（動的
散乱Ｗ）、ゲスト・ホスト型、ＤＡＰ型、二周波法型な
どがあり、それぞれに使用される液晶物質に要求される
性質は異る。Display elements using liquid crystals have come to be widely used in watches, trains, etc. This liquid crystal display element utilizes the properties of optical anisotropy and dielectric anisotropy of liquid crystal materials, and the liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase, among which nematic liquid crystal phase is used. The one used is the one most widely put into practical use. That is, there are TN (twisted nematic) type, DS (dynamic scattering W) type, guest-host type, DAP type, dual-frequency method type, etc., and the properties required of the liquid crystal materials used for each type are different. Ru.
しかし、いずれにしても、これら表示素子に使用される
液晶物質は自然界のなるべく広い範囲で液晶相を示すも
のが望ましいが、現在のところ中−物質でその様な条件
をみたす様な物質はなく、数４１トの液晶物質又は非液
晶物質を混合して一応実用に耐える様な物を得ているの
が現状である。又、これらの物質は水分、光、熱、空気
等に対Ｅ２ても安定でなければならないのは勿論であり
、更に表示素子を駆動させるに必要なしきい電圧、飽和
電圧がなるべく低いこと、又応答速度を早くするために
は粘度が出来るだけ低いことが望ましい。However, in any case, it is desirable that the liquid crystal materials used in these display elements exhibit a liquid crystal phase over as wide a range as possible in nature, but there are currently no intermediate materials that satisfy such conditions. At present, materials that can be put to practical use are obtained by mixing several 41 tons of liquid crystal materials or non-liquid crystal materials. In addition, these substances must of course be stable against moisture, light, heat, air, etc., and must also have a threshold voltage and saturation voltage as low as possible to drive the display element. In order to increase the response speed, it is desirable that the viscosity be as low as possible.
本発明者らは次に示す含フツ素化合物がその様な要件を
満たすものであることを見出し本発明に到達した。The present inventors have discovered that the following fluorine-containing compound satisfies such requirements and have arrived at the present invention.
即ち本発明は一般式 （上式中Ｒは炭素数１〜１０のアルキル基を。That is, the present invention is based on the general formula (In the above formula, R is an alkyl group having 1 to 10 carbon atoms.
唖へは舎又は（Ｙを示す）
で表わされる２、６−ジフルオロ安息香酸のエステル誘
導体及びそれを少くとも一種含有する液晶組成物である
。The present invention relates to an ester derivative of 2,6-difluorobenzoic acid represented by (Y) and a liquid crystal composition containing at least one thereof.
本発明の化合物は高温までネマチック相を示し、しかも
低粘性であシ、誘電異方性値△εは＋０．５程度である
。本発明の化合物を含有する液晶組成物はその誘電異方
性が小さいにもかかわらず、しきい電圧、飽和電圧は低
くなシ、駆動電圧の低い従って消費電力の少ない、液晶
表示素子を得ることを可能にする。本化合物と混合する
液晶化合物は表示装置のタイプ、用途等によシ適宜選択
すればよく、特にＮ−Ｉ点（ネマチック−透明点）の高
い組成物をつくるのに好適である。The compound of the present invention exhibits a nematic phase up to high temperatures, has low viscosity, and has a dielectric anisotropy value Δε of about +0.5. Although the liquid crystal composition containing the compound of the present invention has a small dielectric anisotropy, the threshold voltage and saturation voltage are low, and the driving voltage is low, so that a liquid crystal display element with low power consumption can be obtained. enable. The liquid crystal compound to be mixed with the present compound may be appropriately selected depending on the type of display device, usage, etc., and is particularly suitable for producing a composition with a high NI point (nematic clearing point).
更に本発明の化合物は表示素子に必要な熱、光、湿度、
電気などに対する安定性も有し、又、他の液晶と混ぜた
時に低粘度になる傾向を有している。Furthermore, the compound of the present invention can handle the heat, light, humidity, and
It also has stability against electricity and tends to have a low viscosity when mixed with other liquid crystals.
つぎに本発明の化合物の製造法を示すと、２゜６−ジフ
ルオロ安息香酸クロリドとトランス−４−（トランス−
４−アルキルシクロヘキシル）シクロヘキサノール１−
ｊ４−（）ランス−４−アルキルシクロヘキシルフェノ
ールとをピリジン存在下反応すれば目的の２．６−ジフ
ルオロ安息香酸のエステル誘導体が得られる。これを化
学式で示すと
（Ｒ，やへは前記に同じ）
以下実施例として本発明の化合物の製造例及び使用例を
示して本発明を更に詳細に説明する。Next, the method for producing the compound of the present invention will be described. 2゜6-difluorobenzoic acid chloride and trans-4-(trans-
4-Alkylcyclohexyl)cyclohexanol 1-
By reacting j4-()trans-4-alkylcyclohexylphenol in the presence of pyridine, the desired ester derivative of 2,6-difluorobenzoic acid can be obtained. This is represented by a chemical formula (R and yah are the same as above).The present invention will be explained in more detail below by showing production examples and usage examples of the compounds of the present invention as examples.
実施例１（２，６−ジフルオロ安、低香酸−トランス−
４−（）ランス−４−プロピルシクロヘキシル）シクロ
ヘキシルエステルの製造〕
２．６−ジフルオロ安息香酸クロリド１．８！トドラン
ス−４−（）、５ンスー４−プロピルシクロヘキシル）
シクロヘキ’Ｌ ／ −ル２．２ ！（０，０１モル）
をピリジン５０ｍ／に溶かしたものとを反応さセーた。Example 1 (2,6-difluoroben, low aromatic acid-trans-
Production of 4-() lance-4-propylcyclohexyl)cyclohexyl ester] 2.6-difluorobenzoic acid chloride 1.8! trans-4-(), 5-propylcyclohexyl)
Cyclohek'L/-L2.2! (0.01 mol)
was dissolved in 50ml of pyridine.
反応後トルエン５０ｗｔｔを加え一晩放置後、水１００
ｍ１に注ぎ込む。トルエン層を分離し、６ Ｎ −ｆ■
ｃｔで８回、２ Ｎ −ＮａＯＨ水溶液で３回抽出した
後、トルエン層が完全に中性になるまで水洗してからト
ルエン層を減圧にしてトルエンを留去すると結晶が残る
。それをエタノールで再結晶（〜で目的物である２、６
−ジフルオロ安息香酸−トランス−４−（トランス−４
−プロピルシクロヘキシル）シクロヘキシルエステルを
得た。収量２．５ｆ、収率６８％、Ｃ−Ｎ点８１Ｊ 〜
８１．８°Ｃ，Ｎ−Ｉ点９６６°Ｃであった。After the reaction, add 50 wtt of toluene and leave it overnight, then add 100 wtt of water.
Pour into m1. Separate the toluene layer and add 6 N −f■
After extraction with ct 8 times and 3 times with 2N-NaOH aqueous solution, the toluene layer is washed with water until it becomes completely neutral, and then the toluene layer is reduced in pressure and the toluene is distilled off, leaving crystals. Recrystallize it with ethanol (the target product is 2,6
-difluorobenzoic acid-trans-4-(trans-4
-propylcyclohexyl) cyclohexyl ester was obtained. Yield 2.5f, yield 68%, C-N point 81J ~
The temperature was 81.8°C, and the temperature at the N-I point was 966°C.
実施例２〜１１
実施例１におけるトランス−４−（トランス−４−７’
、ロビルシクロヘキシル）シクロヘキサノールの代シに
他の置換基を有するトランス−４−（）：ｌｔンスー４
−アルキルシクロヘキシル）シクロヘキサノール又は４
−（）ランス−４−アルキルシクロヘキシル）フェノー
ル０．０１モル使用した他は全く同様な操作で第１表に
示す（１）式の化合物を製造した。それらの融点、Ｃ−
Ｎ点、Ｎ−Ｉ点を実施例１の結果と共に第１表に示ず１
゜
第１表
＋１）Ｎ−１点の欄の（）はモノトロピックを示す実施
例１２（使用例）
４−ベンチルー４′−シアノビフェニル５１％（重量、
以下同じ）
４−へブチル−４′−シアノビフェニル３２％
４−オクチルオキシ−４７−シアノビフェニル１７％
なる組成の液晶混合物のＮ−Ｉ点は４４，８°Ｃ５粘度
は２０°Ｃで４０ｃｐ、誘電異方性値は＋１２．４であ
る。それをＴＮセルにしたときのしきい電圧は１．６５
Ｖ、飽和電圧は２．８１Ｖである。Examples 2 to 11 Trans-4-(trans-4-7') in Example 1
, lovylcyclohexyl) cyclohexanol with other substituents in place of trans-4-(): lt-4
-alkylcyclohexyl)cyclohexanol or 4
-()Lance-4-alkylcyclohexyl)phenol A compound of formula (1) shown in Table 1 was produced in exactly the same manner except that 0.01 mol of phenol was used. Their melting point, C-
The N point and N-I point are not shown in Table 1 along with the results of Example 1.
゜Table 1 + 1) The parentheses in the N-1 column indicate monotropic Example 12 (Usage example) 4-Benzyl-4'-cyanobiphenyl 51% (weight,
The same applies hereafter) 32% of 4-hebutyl-4'-cyanobiphenyl and 17% of 4-octyloxy-47-cyanobiphenyl has an N-I point of 44.8°C, a viscosity of 40cp at 20°C, The dielectric anisotropy value is +12.4. When it is made into a TN cell, the threshold voltage is 1.65
V, the saturation voltage is 2.81V.
この液晶混合物９０部に本発明実施例１の２゜６−ジフ
ルオロ安息香酸−トランス−４−（）ランス−４−グロ
ビルシクロヘキシル）シクロヘキシルエステル１０部を
加えた液晶混合物のＮ−Ｉ点は４８．１°Ｃに上昇し、
誘電異方性値は＋１．１．２、粘度は２０’Ｃで８９
ｃｐであった。The N-I point of the liquid crystal mixture obtained by adding 10 parts of 2゜6-difluorobenzoic acid-trans-4-()lans-4-globylcyclohexyl)cyclohexyl ester of Example 1 of the present invention to 90 parts of this liquid crystal mixture was 48. The temperature rose to .1°C,
Dielectric anisotropy value is +1.1.2, viscosity is 89 at 20'C
It was cp.
又、ＴＮセルにしたときのしきい電圧は１．６０Ｖ、飽
和電圧ｔま２．８０Ｖで少し低くなった。Further, when a TN cell was used, the threshold voltage was 1.60V, and the saturation voltage t was 2.80V, which was slightly lower.
Claims (2)
は舎又は（ンを示す） で表わされる２、６−ジフルオロ安息香酸のエステル誘
導体。(1) General formula (in the above formula, R represents an alkyl group having 1 to 10 carbon atoms, Y)
An ester derivative of 2,6-difluorobenzoic acid represented by the following symbol.
＋又は〈ンを示す） で表わされる２、６−ジフルオロ安息香酸のエステル誘
導体を少なくとも一種含有することを特徴とする液晶組
成物。(2) Contains at least one type of ester derivative of 2,6-difluorobenzoic acid represented by the general formula (in the above formula, R represents an alkyl group having 1 to 10 carbon atoms, and group represents + or <). A liquid crystal composition characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2898883A JPS59155338A (en) | 1983-02-23 | 1983-02-23 | Ester derivative of 2,6-difluorobenzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2898883A JPS59155338A (en) | 1983-02-23 | 1983-02-23 | Ester derivative of 2,6-difluorobenzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59155338A true JPS59155338A (en) | 1984-09-04 |
Family
ID=12263792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2898883A Pending JPS59155338A (en) | 1983-02-23 | 1983-02-23 | Ester derivative of 2,6-difluorobenzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59155338A (en) |
-
1983
- 1983-02-23 JP JP2898883A patent/JPS59155338A/en active Pending
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