JPS61277667A - Quinoline derivative - Google Patents
Quinoline derivativeInfo
- Publication number
- JPS61277667A JPS61277667A JP12129785A JP12129785A JPS61277667A JP S61277667 A JPS61277667 A JP S61277667A JP 12129785 A JP12129785 A JP 12129785A JP 12129785 A JP12129785 A JP 12129785A JP S61277667 A JPS61277667 A JP S61277667A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- compound
- alkoxy
- composition
- 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
Landscapes
- Liquid Crystal Substances (AREA)
- Quinoline Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔利用分野〕
本発明は液晶誘電体の１成分として有用な正の誘電異方
性を示す新規な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 [Field of Application] The present invention relates to a novel compound exhibiting positive dielectric anisotropy useful as a component of a liquid crystal dielectric, and a liquid crystal composition containing the same.
光学異方性および誘電異方性を利用した液晶表示素子の
表示方式には、ねじれネマチック（ＴＮ）盤、動的散乱
（Ｄ Ｓ ） Ｗ、ゲストホストａなど各種の方式があ
り、それぞれの方式により使用される液晶物質に望まれ
る性質が異なる。There are various display methods for liquid crystal display elements that utilize optical anisotropy and dielectric anisotropy, such as twisted nematic (TN) disks, dynamic scattering (DS) W, and guest host a. The desired properties of the liquid crystal material used differ depending on the type of liquid crystal material used.
しかし、いずれにしてもこれら液晶表示素子に使用され
る液晶化合物はなるべく広い温度範囲で液晶相を示すも
のが望ましく、また水分、光、熱、空気などに対して安
定であることが必要である。現在のところ単一化合物で
この様な条件をすべて満たすものはなく、多数の化合物
から選ばれた数種の液晶化合物や非液晶化合物を混合し
て実用に供している。本発明の目的はこの様な液晶誘電
体の１成分として使用するのに適する新規な化合物を提
供することである。However, in any case, it is desirable that the liquid crystal compounds used in these liquid crystal display elements exhibit a liquid crystal phase over as wide a temperature range as possible, and they also need to be stable against moisture, light, heat, air, etc. . At present, there is no single compound that satisfies all of these conditions, and several types of liquid crystal compounds and non-liquid crystal compounds selected from a large number of compounds are mixed and put into practical use. It is an object of the present invention to provide new compounds suitable for use as a component of such liquid crystal dielectrics.
本発明は一般式
（上式中Ｙ、ＺはいずれもＦ、ＣＩ、ＣＮ又は炭素数１
〜１０のアルキル基又はアルコキシ基を示すが、２がＦ
、ＣＪＩ’又はＣＮである場合はＹは炭素数１〜１０の
アルキル基又はアルコキシ基である）
で表わされるキノリン誘導体及び少くともその一種を含
有する液晶組成物である。The present invention is based on the general formula (in the above formula, both Y and Z are F, CI, CN or carbon number 1).
~10 alkyl or alkoxy groups, but 2 is F
, CJI' or CN, Y is an alkyl group or an alkoxy group having 1 to 10 carbon atoms) and at least one thereof.
本発明の化合物はそれ自体が液晶相を示さなくても他の
液晶化合物または液晶組成物との相溶性に優れ、かつ化
学的に安定であシ、本発明の化合物を使用することによ
り、その組成物の透明点を＃１とんど降下させることな
く、その組成物を用いた液晶表示素子の駆動電圧を降下
させることができる。Even if the compound of the present invention does not exhibit a liquid crystal phase itself, it has excellent compatibility with other liquid crystal compounds or liquid crystal compositions and is chemically stable. The driving voltage of a liquid crystal display element using the composition can be lowered without lowering the clearing point of the composition by #1.
又、本発明の（１）式の化合物と混合して液晶組成物゛
を構成する液晶化合物としてはシック塩基系化合物、ア
ゾキシ系化合物、ニス７一ル系化合物、ヒフェニル系化
合物、フェニルシクロヘキサン系化合物、フェニルピリ
ジン系化合物等をあげることができる。Further, examples of liquid crystal compounds that can be mixed with the compound of formula (1) of the present invention to form a liquid crystal composition include thick basic compounds, azoxy compounds, varnish compounds, hyphenyl compounds, and phenylcyclohexane compounds. , phenylpyridine compounds, etc.
次に本発明の化合物の製造法について述べると、まず６
−置換−２−メチルキノリンと置換ベンズアルデヒドと
を無水酢酸の存在下、脱水縮合させることによシ２−〔
β−（置換フェニル）ビニル〕−６−置換キノリン（ｎ
）を得る。次に化合物（ＩＩ）をＰｄ／ｃなどの触媒を
用いて接触還元することによシ、化合物（１）を得る。Next, the method for producing the compound of the present invention will be described.
2-[
β-(substituted phenyl)vinyl]-6-substituted quinoline (n
). Next, compound (1) is obtained by catalytically reducing compound (II) using a catalyst such as Pd/c.
以上を反応式で示すと次のようになる。The reaction formula for the above is as follows.
（Ｉ）
〔実施例〕
以下、実施例により、本発明の化合物について更に詳細
に説明する。(I) [Example] Hereinafter, the compound of the present invention will be explained in more detail with reference to Examples.
実施例１
〔２−〔β−（４−ｎ−プロポキシフェニル）エチルツ
ー６−フルオロキノリン（（１）式でＹ＝＝Ｃ３Ｈ７０
，Ｚ＝ＦＯもの）の製造〕（＋） ２− （β−（４−
ｎ−プロポキシフェニル）ビニルクー６−フルオロキノ
リンの製造６−フルオロ−２−メチルキノリンｌｏ、ｃ
ｌ、４−ｎ−プロポキシベンズアルデヒド１０．２ Ｆ
。Example 1 [2-[β-(4-n-propoxyphenyl)ethyl-6-fluoroquinoline (Y==C3H70 in formula (1)
, Z=FO)] (+) 2- (β-(4-
Preparation of n-propoxyphenyl) vinyl 6-fluoroquinoline 6-fluoro-2-methylquinoline lo, c
l,4-n-propoxybenzaldehyde 10.2 F
.
無水酢酸７．６ｔの混合溶液を２５時間加熱還流し・、
冷却後析出した固体をメタノールで洗滌し、この固体を
エタノールより再結晶し、まず２−〔β−（４−ｎ −
１７’ロポキシフエニル）ビニルクー６−フルオロキノ
リン１３１Ｆを得た。この化合物は１２８℃と１４５℃
の間でネマチック液晶相を示した。A mixed solution of 7.6 t of acetic anhydride was heated under reflux for 25 hours.
After cooling, the precipitated solid was washed with methanol, and this solid was recrystallized from ethanol.
17'Ropoxyphenyl) vinyl 6-fluoroquinoline 131F was obtained. This compound is 128℃ and 145℃
It showed a nematic liquid crystal phase between the two.
（ｉｉ）標題化合物の製造
（１）で得られた２−〔β−（４−ｎ−プロポキシフェ
ニル）ビニルクー６−フルオロキノリンｌｏｆを）ルエ
ン２００−に溶解し、パラジウム−炭素２？を加え、常
温、常圧で接続還元を行なった。反応終了後触媒を戸別
し、溶媒を減圧留去して残った固体をエタノールよシ再
結晶し、目的とする２−〔β−（４−ｎ−プロポキシフ
ェニル）エチル） −６−フルオロキノリン８２を得た
。この化合物は液晶相は示さず、その融点は６２．３〜
６３．３℃であった。(ii) Preparation of the title compound The 2-[β-(4-n-propoxyphenyl)vinyl 6-fluoroquinoline lof obtained in (1)] was dissolved in 200-toluene, and the palladium-carbon 2? was added, and connection reduction was carried out at room temperature and pressure. After the reaction, the catalyst was separated, the solvent was distilled off under reduced pressure, and the remaining solid was recrystallized from ethanol to obtain the desired 2-[β-(4-n-propoxyphenyl)ethyl)-6-fluoroquinoline 82 I got it. This compound does not show a liquid crystal phase and its melting point is 62.3~
The temperature was 63.3°C.
実施例２
２−〔β−（４−シアノフェニル）エチル〕−６−メド
キシキノリン（（Ｉ）式でＹ＝Ｃ７’Ｊｗｚ＝ＣＨ３０
のもの）の製造
実施例１に於ける６−フルオロ−２−メチルキノリン、
４−ｎ−プロポキシベンズアルデヒ）’ ｆｐ 代りに
夫々６−メドキシー２−メチルキノリン、４−シアノベ
ンズアルデヒドを用いた他は、実施例１と同様にして目
的とする２−〔β−（４−シアノフェニル）エチルクー
６−メドキシキノリンを得た。この化合物は液晶相は示
さず、その融点は１２０．２〜１２１．１℃であった。Example 2 2-[β-(4-cyanophenyl)ethyl]-6-medoxyquinoline (Y=C7'Jwz=CH30 in formula (I)
6-fluoro-2-methylquinoline in Production Example 1 of
The desired 2-[β-(4-cyanobenzaldehyde) Phenyl)ethyl-6-medoxyquinoline was obtained. This compound did not exhibit a liquid crystal phase, and its melting point was 120.2-121.1°C.
実施例３（応用例）
なる液晶組成物（Ａ）のネマチック−透明点（Ｎ−１点
）は５２．１℃、誘電異方性値は＋１１．２、光学異方
性値は０．１１９である。これをセル厚１０μｍのＴＮ
セルに封入した液晶セルの２０℃におけるしきい値電圧
は１．５４Ｖ、飽和電圧は２．１３ Ｖであった。この
液晶組成物（Ａ）９ｏｗｔ％と実施例２で製造した２−
〔β−（４−シアノフェニル）エチルクー５−メトキシ
キノリン１０ｗｔ％とから成る組成物（Ｂ）のＮ−１点
は５２．０℃、誘電異方性値は＋１２．８、光学異方性
値は０．１２７であシ、このものを前述のＴＮセルに封
入した液晶セルの２０℃におけるしきい値電圧は１．３
９ Ｖ 、飽和電圧は１．９６Ｖであった。Example 3 (Application example) The nematic clearing point (N-1 point) of the liquid crystal composition (A) is 52.1°C, the dielectric anisotropy value is +11.2, and the optical anisotropy value is 0.119. It is. This is made of TN with a cell thickness of 10 μm.
The liquid crystal cell sealed in the cell had a threshold voltage of 1.54V and a saturation voltage of 2.13V at 20°C. This liquid crystal composition (A) 9wt% and 2-
[The N-1 point of the composition (B) consisting of 10 wt% of β-(4-cyanophenyl)ethyl-5-methoxyquinoline is 52.0°C, the dielectric anisotropy value is +12.8, and the optical anisotropy value is 0.127, and the threshold voltage of the liquid crystal cell sealed in the above-mentioned TN cell at 20°C is 1.3.
9 V, and the saturation voltage was 1.96 V.
以上that's all
Claims (2)
１〜１０のアルキル基又はアルコキシ基を示すが、Ｚが
Ｆ、Ｃｌ又はＣＮである場合はＹは炭素数１〜１０のア
ルキル基又はアルコキシ基である） で表わされるキノリン誘導体。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the above formula, Y and Z each represent F, Cl, CN, or an alkyl group or alkoxy group having 1 to 10 carbon atoms, When Z is F, Cl or CN, Y is an alkyl group or an alkoxy group having 1 to 10 carbon atoms.
〜１０のアルキル基を示すが、ＺがＦ、Ｃｌ又はＣＮで
ある場合はＹは炭素数１〜１０のアルキル基又はアルコ
キシ基である） で表わされるキノリン誘導体の一種を少くとも１成分含
有する液晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (In the above formula, Y and Z are either F, Cl, CN, or have a carbon number of 1
-10 alkyl group, and when Z is F, Cl or CN, Y is an alkyl group or alkoxy group having 1 to 10 carbon atoms) Contains at least one component of a type of quinoline derivative represented by liquid crystal composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12129785A JPS61277667A (en) | 1985-06-04 | 1985-06-04 | Quinoline derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12129785A JPS61277667A (en) | 1985-06-04 | 1985-06-04 | Quinoline derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61277667A true JPS61277667A (en) | 1986-12-08 |
Family
ID=14807772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12129785A Pending JPS61277667A (en) | 1985-06-04 | 1985-06-04 | Quinoline derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61277667A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011517665A (en) * | 2008-03-11 | 2011-06-16 | メルク パテント ゲーエムベーハー | Compounds having electroluminescent or electron transport properties |
-
1985
- 1985-06-04 JP JP12129785A patent/JPS61277667A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011517665A (en) * | 2008-03-11 | 2011-06-16 | メルク パテント ゲーエムベーハー | Compounds having electroluminescent or electron transport properties |
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