JPH0262862A - Pyridine derivative - Google Patents
Pyridine derivativeInfo
- Publication number
- JPH0262862A JPH0262862A JP21563688A JP21563688A JPH0262862A JP H0262862 A JPH0262862 A JP H0262862A JP 21563688 A JP21563688 A JP 21563688A JP 21563688 A JP21563688 A JP 21563688A JP H0262862 A JPH0262862 A JP H0262862A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound expressed
- liquid crystal
- compound
- chain alkyl
- 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
- 150000003222 pyridines Chemical class 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 239000000203 mixture Substances 0.000 abstract description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 239000012769 display material Substances 0.000 abstract description 2
- 238000007269 dehydrobromination reaction Methods 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000004973 liquid crystal related substance Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- NTSLROIKFLNUIJ-UHFFFAOYSA-N 5-Ethyl-2-methylpyridine Chemical compound CCC1=CC=C(C)N=C1 NTSLROIKFLNUIJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical class CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野コ
本発明は電気光学的表示材料として用いられる新規液晶
化合物であるピリジン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a pyridine derivative which is a novel liquid crystal compound used as an electro-optical display material.
［発明の概要］
本発明は一般式
％式％（１）
（式中Ｒ１は 炭素数１〜１２の直鎖アルキル基又はア
ルコキシ基、Ｒ２は炭素数１〜１２の直鎖アルキル基を
示し、シクロヘキサン環はトランス配置である。）で表
わされるピリジン誘導体であり、ネマチック相を有する
新規液晶化合物である。本発明の化合物は他の液晶化合
物と混合して液晶組成物とした場合、屈折率異方性（Δ
ＴＬ）を大きくする特徴を持つ。したがって本発明の化
合物を混合した液晶組成物を用いることにより、セルの
淳さを小さくすることができる。[Summary of the Invention] The present invention is based on the general formula % (1) (wherein R1 represents a straight chain alkyl group or alkoxy group having 1 to 12 carbon atoms, R2 represents a straight chain alkyl group having 1 to 12 carbon atoms, It is a pyridine derivative represented by (the cyclohexane ring has a trans configuration) and is a new liquid crystal compound having a nematic phase. When the compound of the present invention is mixed with other liquid crystal compounds to form a liquid crystal composition, the refractive index anisotropy (Δ
It has the characteristic of increasing TL). Therefore, by using a liquid crystal composition containing the compound of the present invention, the density of the cell can be reduced.
［従来の技術］
液晶表示装置（ＬＧＤ）は液晶の持つ電気光学効果を利
用した表示装置である。液晶にはネマチック相（Ｎ）、
スメ□タチック相（Ｓ）、コレステリック相（Ｏｈ）な
どの相が知られており、これら３相ともにそれぞれ固有
の電気光学効果を利用してＬＯＤとして用いられている
が、そのうちネマチック相を用いたＬＯＤが最も広く普
及してぃる。またネマチック相を用いたＬＯＤの表示方
式にはねじれネマチック型（ＴＮ型）、動的散乱型（Ｄ
ＳＭ型）、ゲスト・ホスト型（ＧＨ型）ＳＳＴＮ型、Ｓ
ＢＩ！：型などがある。[Prior Art] A liquid crystal display device (LGD) is a display device that utilizes the electro-optic effect of liquid crystal. The liquid crystal has a nematic phase (N),
Phases such as smetatic phase (S) and cholesteric phase (Oh) are known, and each of these three phases is used as an LOD by utilizing the unique electro-optic effect. LOD is the most widely used. In addition, display methods for LOD using a nematic phase include twisted nematic type (TN type), dynamic scattering type (D
SM type), guest-host type (GH type) SSTN type, S
BI! : There are types, etc.
ＬＯＤは小型で薄くでき、駆動電圧が低く消費電力が小
さく、また受光素子であることから長時間使用しても目
が疲れない等の長所を有することから、従来よりウォッ
チ、電卓、オーディオ機器、各種計測器９乗用車のダツ
シュボード等の表示装置として広く応用されている。ま
た最近ではパーソナルコンピューターやワードプロセッ
サーのデイスプレィ、白黒さらにはカラーのポケットテ
レビなど画素数の非常に多い表示装置にも応用されてお
り、ＯＲＴに代わる表示装置として注目を集めている。LODs can be made small and thin, have low driving voltage, consume little power, and because they are light-receiving elements, they can be used for long periods of time without tiring the eyes. Various Measuring Instruments 9 Widely used as display devices for dashboards of passenger cars, etc. Recently, it has also been applied to display devices with a large number of pixels, such as personal computer and word processor displays, black and white and even color pocket televisions, and is attracting attention as a display device that can replace ORT.
このよ５にＬＱＤはその長所ゆえにたいへん広く用いら
れており、特にその電気光学的な応答速度を速くするこ
とでさらに応用分野は＼
拡大する。LQDs are very widely used due to their advantages, and their field of application will further expand by increasing their electro-optical response speed.
［発明が解決しようとする課題］
単一の液晶化合物で実用温度範囲、電気光学的応答性を
満たすものはなく、数種類のネマチック液晶化合物を混
合した液晶組成物を用いている。[Problems to be Solved by the Invention] There is no single liquid crystal compound that satisfies the practical temperature range and electro-optic response, and a liquid crystal composition that is a mixture of several types of nematic liquid crystal compounds is used.
この液晶組成物を用いたＴＮ型セルで応答速度を速くす
るために、そのセル厚を小さくする必要があり、このよ
うなセルを実現するためにはΔルの大きな液晶組成物を
用いる。しかし従来の化合物では充分に大きなΔルを持
つ液晶組成物が得られなかった。In order to increase the response speed of a TN type cell using this liquid crystal composition, it is necessary to reduce the cell thickness, and in order to realize such a cell, a liquid crystal composition with a large ΔR is used. However, with conventional compounds, it has not been possible to obtain a liquid crystal composition with a sufficiently large ΔR.
本発明はこのような実状における要請に答えるものであ
り、その目的は他の１種又は２種以上のネマチック液晶
化合物と混合することにより、Δルの大きな液晶組成物
を得ることができる新規なネマチック液晶化合物を提供
することである。The present invention is intended to meet the needs of the above-mentioned situation, and its purpose is to provide a novel liquid crystal composition that can obtain a liquid crystal composition with a large ΔL by mixing it with one or more other nematic liquid crystal compounds. An object of the present invention is to provide a nematic liquid crystal compound.
［課題を解決するための手段］
本発明は一般式
％式％（１）
（式中Ｒ１は炭素数１〜１２の直鎖アルキル基又はアル
コキシ基、Ｒ２は炭素数１〜１２の直鎖アルキル基を示
し、シクロヘキサン環はトランス配置である。）で゛表
わされるピリジン誘導体。[Means for Solving the Problems] The present invention is based on the general formula % (1) (wherein R1 is a straight-chain alkyl group or alkoxy group having 1 to 12 carbon atoms, and R2 is a straight-chain alkyl group having 1 to 12 carbon atoms. cyclohexane ring is in trans configuration).
本発明のピリジン誘導体（１）は次の製造方法により得
ることができる。The pyridine derivative (1) of the present invention can be obtained by the following production method.
Ｒ１−９−（！Ｈ３（２） Ｒ２ｅＯＨＯ（３
）置である。）
工程１ 化合物（２）と過剰の化合物（３）を無水酢酸
中で縮合して化合物（４）を得る。R1-9-(!H3(2) R2eOHO(3
). ) Step 1 Compound (2) and excess compound (3) are condensed in acetic anhydride to obtain compound (4).
工程２ 化合物（４）にエチルエーテル又はクロロホル
ム中で臭素を付加させて化合物（５）を得る。Step 2 Compound (5) is obtained by adding bromine to compound (4) in ethyl ether or chloroform.
工程３ 化合物（５）をエタノール中、水酸化カリウム
により脱臭化水素化して本発明のピリジン誘導体（１）
を得る。Step 3 Compound (5) is dehydrobrominated with potassium hydroxide in ethanol to obtain the pyridine derivative (1) of the present invention.
get.
Ｒ１−Ｑ−ＯＨＢｒ−ＯＨＥｒ−＠−０−Ｒ２Ｒｈ −
Ｑ−Ｏｗｍ Ｏ−＠−＠−Ｒ２（式中旧 は炭素数１〜
１２の直鎖アルキル基又はアルコキシ基、Ｒ２は炭素数
１〜１２の直鎖アルキル基を示し、シクロヘキサン環は
トランス配［実施例］
以下（実施例と応用例により本発明をさらに詳、頂く説
明する。R1-Q-OHBr-OHEr-@-0-R2Rh −
Q-Owm O-@-@-R2 (old in the formula has 1 or more carbon atoms)
12 straight chain alkyl group or alkoxy group, R2 represents a straight chain alkyl group having 1 to 12 carbon atoms, and the cyclohexane ring is trans-configured. do.
（実施例）
２−メチル−５−エチルピリジン４１．９ ｆ 、 ４
−（ト５ンスー４′−ペンチルシクロヘキシル）ベンズ
アルデヒド１４０．Ｏｒ、無水酢酸８５ｍを混合し、攪
拌しながら４０時間還流した。反応溶液を水に加え、ク
ロロホルムで抽出し、水で洗浄した後クロロホルムを留
去した。これをエタノールから再結晶して次の化合物４
４．１ Ｆを得た。(Example) 2-methyl-5-ethylpyridine 41.9 f, 4
-(5-4'-pentylcyclohexyl)benzaldehyde 140. Or and 85 ml of acetic anhydride were mixed and refluxed for 40 hours with stirring. The reaction solution was added to water, extracted with chloroform, washed with water, and then chloroform was distilled off. This was recrystallized from ethanol to form the following compound 4.
4.1 F was obtained.
０２Ｈ５−９−ＯＨ： （！Ｈ−＠−０−（１５Ｈ１１
この化合物４ａ、Ｏｆを１２００．Ｏｄのエチルエーテ
ルに溶解し、氷水で冷却し、攪拌しながら臭素５５．１
１を滴下した。そのまま３時間攪拌をつづけ、次にピロ
亜硫酸す） ＩＪウム水溶液を加え攪拌した。エチルエ
ーテル層にクロロホルムを加え結晶を溶解し、これを水
で洗浄して溶媒を留去した。残留物をクロロホルム、ア
セトン混合溶媒から再結晶して次の化合物３１０ｔを得
た。02H5-9-OH: (!H-@-0-(15H11
This compound 4a, Of 1200. Bromine 55.1 was dissolved in ethyl ether, cooled with ice water, and stirred.
1 was added dropwise. Stirring was continued for 3 hours, and then an aqueous solution of pyrosulfite was added and stirred. Chloroform was added to the ethyl ether layer to dissolve the crystals, which was washed with water and the solvent was distilled off. The residue was recrystallized from a mixed solvent of chloroform and acetone to obtain the following compound 310t.
０２ Ｈ５−Ｑ−ＯＲＢｒ−ＣＨＢｒ−９−４−０５Ｈ
１ｔごの化合物９．０２を水酸化カリウム２．８１のエ
タノール１２．５ｄ溶液に加え、１４５℃で２０時間還
流した。冷却後水を加え、生成物をＦ取し、これをエタ
ノールから再結晶して目的物である次の化合物５．４ｆ
を得た。02 H5-Q-ORBr-CHBr-9-4-05H
9.02 of the compound per 1 t was added to a solution of 2.81 potassium hydroxide in 12.5 d of ethanol, and the mixture was refluxed at 145° C. for 20 hours. After cooling, water was added, the product was collected as F, and this was recrystallized from ethanol to obtain the target compound 5.4f.
I got it.
０２ Ｈ５−Ｑ−Ｏｍ ｏ−＠−＠−ａ ５ Ｈ１１相
転移温度
Ｃ→ Ｓ ８α９℃
Ｓ、→ Ｎ８９．０℃
Ｎ → 工１９ａ６℃
（ここで０は結晶、Ｓはスメクチック相、Ｎはネマチッ
ク相、工は等方性液体を示す。）（応用例）
第１表に示す液晶組成物Ａを作った。02 H5-Q-Om o-@-@-a 5 H11 phase transition temperature C→S 8α9℃ S, → N89.0℃ N → 19a6℃ (where 0 is crystal, S is smectic phase, N is nematic (Phase and number indicate isotropic liquid.) (Application example) Liquid crystal composition A shown in Table 1 was prepared.
実施例の化合物を含む液晶組成物Ｂを第２表に示す。Liquid crystal composition B containing the compounds of Examples is shown in Table 2.
［発明の効果］
以上述べたように、本発明の液晶化合物は従来の液晶組
成物と混合することにより、Δルの大きな液晶組成物を
与えることができる。よって、本発明の液晶化合物はネ
マチック液晶組成物の混合成分としてたいへん有用であ
る。[Effects of the Invention] As described above, by mixing the liquid crystal compound of the present invention with a conventional liquid crystal composition, a liquid crystal composition with a large ΔR can be provided. Therefore, the liquid crystal compound of the present invention is very useful as a mixed component of a nematic liquid crystal composition.
以上
組成物ＡおよびＢのＮ−１点、２０℃におけるΔルの測
定結果を次に示す。The measurement results of ΔR of compositions A and B at point N-1 and 20° C. are shown below.
Claims (1)
コキシ基、Ｒ２は炭素数１〜１２の直鎖アルキル基を示
し、シクロヘキサン環はトランス配置である。）で表わ
されるピリジン誘導体。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (1) (In the formula, R1 is a straight chain alkyl group or alkoxy group having 1 to 12 carbon atoms, and R2 is a straight chain having 1 to 12 carbon atoms. A pyridine derivative represented by (representing an alkyl group, and the cyclohexane ring is in a trans configuration).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21563688A JPH0262862A (en) | 1988-08-30 | 1988-08-30 | Pyridine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21563688A JPH0262862A (en) | 1988-08-30 | 1988-08-30 | Pyridine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0262862A true JPH0262862A (en) | 1990-03-02 |
Family
ID=16675686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21563688A Pending JPH0262862A (en) | 1988-08-30 | 1988-08-30 | Pyridine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0262862A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5831660A (en) * | 1995-01-18 | 1998-11-03 | Olympus Optical Co., Ltd. | Electrostatic recording head |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01502283A (en) * | 1987-02-12 | 1989-08-10 | ヴアル，ハンス | Sanitary boxes for public purposes |
-
1988
- 1988-08-30 JP JP21563688A patent/JPH0262862A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01502283A (en) * | 1987-02-12 | 1989-08-10 | ヴアル，ハンス | Sanitary boxes for public purposes |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5831660A (en) * | 1995-01-18 | 1998-11-03 | Olympus Optical Co., Ltd. | Electrostatic recording head |
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