JPS6025973A - Pyrimidine compound - Google Patents
Pyrimidine compoundInfo
- Publication number
- JPS6025973A JPS6025973A JP13249783A JP13249783A JPS6025973A JP S6025973 A JPS6025973 A JP S6025973A JP 13249783 A JP13249783 A JP 13249783A JP 13249783 A JP13249783 A JP 13249783A JP S6025973 A JPS6025973 A JP S6025973A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- tetraaza
- terphenyl
- 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
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、新規な有機化合物に関し更に詳しくは液晶材
料の成分として有用である新規な液晶化合物に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel organic compounds, and more particularly to novel liquid crystal compounds useful as components of liquid crystal materials.
周知の如く液晶物質はねじれた液晶配列を持つネマチッ
ク７１に品を月」いる表示素子（いわゆるＴＮセル）に
利用できる他適当な色素を含有する液晶物質又は液晶混
合物のゲスト・ホスト効果を応用した表示素子、更には
′／Ｉり晶の動的散乱効果を利用したＤＳ型表示素子、
コレステリック−ネマチック相転移を利用した表示素子
、液晶のヒ界制亜複屈折効果を利用したＤＡ’Ｐ型表示
素子等広く利用されている。これらの液晶表示素子に封
入する材料は単独の化合物ではその諸特性即ち、液晶温
度範囲、動作電圧、応答性能等で実用的なイ吏用に使用
し鋪、＜数棟の液晶化合物を混合して実用に供している
。As is well known, liquid crystal materials can be used in display elements (so-called TN cells) that are based on nematic materials having a twisted liquid crystal arrangement, and can also be applied to the guest-host effect of liquid crystal materials or liquid crystal mixtures containing appropriate pigments. Display elements, and furthermore, DS type display elements that utilize the dynamic scattering effect of '/I crystals,
Display elements that utilize cholesteric-nematic phase transition and DA'P type display elements that utilize the field suppressed subbirefringence effect of liquid crystals are widely used. The materials encapsulated in these liquid crystal display elements cannot be used as a single compound for practical use due to their various characteristics, such as liquid crystal temperature range, operating voltage, response performance, etc.; It is put into practical use.
本発明はこの様な実用的なかつ優れたかつ安定な液晶組
成物を構成する成分として有用な化合物を提供するもの
である。The present invention provides a compound useful as a component constituting such a practical, excellent and stable liquid crystal composition.
即ち本発明の第一は、一般式
（上式中几１、■も２は炭素数１〜１０のアルキル基を
示す。）
にて表わされる４、４″−ジアルキル−２，６，２”
、 ６”−テトラアザ−ｐ−テルフェニルである。That is, the first aspect of the present invention is 4,4"-dialkyl-2,6,2" represented by the general formula (in the above formula, 1 and 2 represent an alkyl group having 1 to 10 carbon atoms).
, 6''-tetraaza-p-terphenyl.
本発明の第二は、一般式（１）（式中、Ｒ，、几２は前
記の意味をもつ）で表わされる４、４“−ジアルキル−
２，６，２”、ｆ’ｉ”−テトラアザ−ｐ−テルフェニ
ルを含有することを特徴とする液晶組成物である。The second aspect of the present invention is a 4,4"-dialkyl-
This is a liquid crystal composition characterized by containing 2,6,2'', f'i''-tetraaza-p-terphenyl.
本発明の化合物（１）は、力ｊＥ折率のＶ“に方性が著
しく大きく、３環の化合物としては低粘度であり、液晶
／＋１晋度範囲が相当に広く、ツボ性に１２ンれた液晶
化合物である。The compound (1) of the present invention has a significantly large orientation in the force jE refractive index V'', has a low viscosity for a three-ring compound, has a considerably wide liquid crystal/+1 conductivity range, and has a potency of 12 It is a liquid crystal compound.
本発明の化合物は、他の液晶化合物との相浴性が優れて
いるので、例えば、ビフェニル系、エステル系、シクロ
へキナンカルボン酸フェニルエステル系、フェニルシク
ロヘキサン基、フェニルメタジオギサン系、フェニルピ
リミジン系などのｌ液晶の一石ｆ類又は数４１１−類の
系の化合物と混合させることにより、ｊ心答諸特性やコ
ントラストやシャープネスを向上さぜ、壕だＩｆｋ品温
度朝囲を広げるわ９には開値ｉＪＬ圧をあ丑９」１昇さ
せないなどの効果を発’＋１ｌｔ＝させることができる
。The compound of the present invention has excellent compatibility with other liquid crystal compounds, so it can be used, for example, in biphenyl, ester, cyclohequinanecarboxylic acid phenyl ester, phenylcyclohexane, phenyl metadiogythane, phenylpyrimidine, etc. By mixing liquid crystals with compounds of the F class or number 411-class series, the various characteristics, contrast and sharpness of liquid crystals can be improved, and the temperature range of the product can be expanded. It is possible to produce an effect such as not increasing the opening value iJL pressure by 1'+1lt=.
本発明の化合物は、次のような反１．−６式に従って合
成することができる。The compounds of the present invention have the following anti-1. -It can be synthesized according to Equation 6.
寸ず、化合物（ＩＩ）のｐ−（５−アルキル−２−ピリ
ミジニル）ベンゾニトリルを出発原料として、これをア
ルコール溶媒中にて塩化水素ガスを反履させて、化合物
（１）のイミドエーテル塩酸塩誘導体を得る。First, using p-(5-alkyl-2-pyrimidinyl)benzonitrile of compound (II) as a starting material, hydrogen chloride gas was evaporated in an alcohol solvent to obtain imidoether hydrochloric acid of compound (1). A salt derivative is obtained.
次に、化合物（１）にアルコール溶媒中にてアンモニア
ガスを反応させて、化合物（ｆｆ）のアミジン塩酸塩誘
導体を得る。Next, compound (1) is reacted with ammonia gas in an alcohol solvent to obtain an amidine hydrochloride derivative of compound (ff).
最後に、化合物（１りと化合物（Ｖ）のアクロレイン誘
導体とを適当な塩基触媒（たとえば、金属アルコラード
、水酸化ナトリウム、１，８−ジアザビシクロ（５，４
，０） −”７−ウンデセンなど）の存在下にて、縮合
環化反応を行ない目的の化合物（１）を得る。Finally, the compound (1) and the acrolein derivative of compound (V) are reacted with a suitable base catalyst (e.g., metal alcoholade, sodium hydroxide, 1,8-diazabicyclo(5,4
, 0) -"7-undecene, etc.), a condensation cyclization reaction is carried out to obtain the target compound (1).
以下実施例により、本発明の詳細な説明する。The present invention will be described in detail below with reference to Examples.
実施例１
４−ペンテルー４“−プロピル−２，６，２”、６“−
テトラアザ−ｐ−テルフェニル
３０ｍ１の無水メタノール中に１．２ ｆ （０，０３
１ηＯＪ）の水酸化ナトリウムを溶解し、これにｐ−（
５−ペンナル−２−ピリミジニル）ベンズアミジン塩酸
塩５゜０７（○、○］、 ４ ｍｏｊ７ ）および、α
−プロピル−β−ジメチルアミノアクロレイン２．４９
（０，０１″？ ｍｏｂ ）を加えた。その次に、１
１：乏拌しながら２時間煮沸した後にメタノールを留去
した。反応残７■イにトルエン５０ ｍｅを加え生成物
を抽出し、抽出液を水洗後、無水硫酸ナトリウム上にて
トルエンハｆｉを乾燥し、その後にトルエンを留去して
残った固形物をエタノ−／ル５０ｍ１からＭ ｒｒＭ品
して、目的の化合物４−ペンチル−４“−プロピル−２
，６，２“、６″−テトラアザ−ｐ−テルフェニル２．
５９ （０，００′７’２ｍｏｌ ）を得た。この化合
物の結晶−イ・マブーック相転移点（Ｃ−Ｎ点と略記す
る）は１４７℃、ネマチック相−等方性液相転移点（Ｎ
−１点と略記する）は１９９℃であった。Example 1 4-pentelium 4"-propyl-2,6,2",6"-
Tetraaza-p-terphenyl 1.2 f (0,03
1ηOJ) of sodium hydroxide was dissolved, and p-(
5-penal-2-pyrimidinyl)benzamidine hydrochloride 5゜07 (○,○], 4 moj7) and α
-Propyl-β-dimethylaminoacrolein 2.49
(0,01″? mob) was added. Then, 1
1: After boiling for 2 hours with poor stirring, methanol was distilled off. 50 me of toluene was added to the reaction residue 7(a) to extract the product, and after washing the extract with water, the toluene hafi was dried over anhydrous sodium sulfate, and then the toluene was distilled off and the remaining solid was evaporated with ethanol. The desired compound 4-pentyl-4"-propyl-2
,6,2",6"-tetraaza-p-terphenyl2.
59 (0,00'7'2 mol) was obtained. The crystal-I-Mabuk phase transition point (abbreviated as C-N point) of this compound is 147°C, and the nematic phase-isotropic liquid phase transition point (N
-1 point) was 199°C.
また、この化合物の元素分析値は次の如＜ｄｌ”算値と
よく一致している。Moreover, the elemental analysis value of this compound is in good agreement with the following calculated value.
実施例２（使用例１）
からなる液晶組成物φ）のＮ−Ｉ点は、５２．１℃、２
０℃における粘度η２０ば２３，４ ｃＰ−誘電異方性
△εばｌ’１．２’（εｔｒ”” １５．９、εＬ＝、
４．’７ ’）でこれをセル厚１０μｍのＴＮセルに
封入したものの閾値電圧は１．５４ Ｖ 、飽、和電圧
は２．１’３’Ｖであり、屈折率異方性△ｎは０．１１
９（ｎｅ＝１．７’ｉ ０９、ｎｏ ＝ １．４９０）
であった。。Example 2 (Usage Example 1) The N-I point of the liquid crystal composition φ) consisting of
Viscosity at 0℃ η20 23,4 cP - Dielectric anisotropy Δε 1'1.2'(εtr"" 15.9, εL=,
4. '7') sealed in a TN cell with a cell thickness of 10 μm, the threshold voltage is 1.54 V, the saturation and sum voltages are 2.1'3' V, and the refractive index anisotropy Δn is 0. 11
9 (ne = 1.7'i 09, no = 1.490)
Met. .
該液晶化合物へ）８５止量部に、本発明の示す化合物４
−ペンチル−４“−プロピル−２ｒ ６．２″＋６“−
テトラアザ−ｐ−テルフェニルを１５東敏部加えた液晶
組成物のＮ−ｉ点は６８．９℃に上ゲ１．シ、η２０は
２６．’６ ｃＰ、△εは１０．９ （ε〃＝１５．３
、εｉ＝ ４．４ ’）で、これを同じＴＮセルに封入
したものの閾値電圧は１．６５ Ｖ 、飽和電圧は２゜
２４Ｖであり、△ｎば○。１４１と上昇した。Compound 4 of the present invention is added to 85 parts of the liquid crystal compound.
-Pentyl-4"-Propyl-2r 6.2"+6"-
The Ni point of the liquid crystal composition containing 15% of tetraaza-p-terphenyl was 68.9°C. , η20 is 26. '6 cP, △ε is 10.9 (ε〃=15.3
, εi=4.4'), and when this is sealed in the same TN cell, the threshold voltage is 1.65 V, the saturation voltage is 2°24 V, and △n is ○. It rose to 141.
以上that's all
Claims (2)
す。） にて表わされる４、４“−ジアルキル−２，６，２“。 ６“−テトラアザ−ｐ−テルフェニル。(1) 4,4"-dialkyl-2,6,2" represented by the general formula (in the above formula, R and R2 represent an alkyl group having 1 to 10 carbon atoms). 6″-Tetraaza-p-terphenyl.
ル基を示す。） にて表わされる４ 、 ４″−ジアルキル−２，６，２
“。 ６“−テトラアザ−ｐ−テルフェニルを含有してなる液
晶組成物。(2) 4,4″-dialkyl-2,6,2 represented by the general formula (141.R21d in the formula 1 represents an alkyl group having 1 to 10 carbon atoms)
A liquid crystal composition containing "6"-tetraaza-p-terphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13249783A JPS6025973A (en) | 1983-07-20 | 1983-07-20 | Pyrimidine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13249783A JPS6025973A (en) | 1983-07-20 | 1983-07-20 | Pyrimidine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6025973A true JPS6025973A (en) | 1985-02-08 |
| JPH0368866B2 JPH0368866B2 (en) | 1991-10-30 |
Family
ID=15082750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13249783A Granted JPS6025973A (en) | 1983-07-20 | 1983-07-20 | Pyrimidine compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6025973A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609485A (en) * | 1984-02-17 | 1986-09-02 | Chisso Corporation | Bipyrimidinyl derivatives |
| US4640796A (en) * | 1984-12-27 | 1987-02-03 | Chisso Corporation | 1,4-dipyrimidinylbenzene derivative |
| US4715984A (en) * | 1985-01-22 | 1987-12-29 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline dihydroazines |
| JPS63278992A (en) * | 1987-05-12 | 1988-11-16 | Fujitsu Ltd | Phase transition liquid crystal composition |
| US5948551A (en) * | 1994-07-01 | 1999-09-07 | Hoechst Aktiengesellschaft | Use of conjugated compounds containing pyrimidine groups as electroluminescence materials |
| JP2010509781A (en) * | 2006-11-14 | 2010-03-25 | オスラム オプト セミコンダクターズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Novel highly conductive organic charge carrier transport material |
-
1983
- 1983-07-20 JP JP13249783A patent/JPS6025973A/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609485A (en) * | 1984-02-17 | 1986-09-02 | Chisso Corporation | Bipyrimidinyl derivatives |
| US4640796A (en) * | 1984-12-27 | 1987-02-03 | Chisso Corporation | 1,4-dipyrimidinylbenzene derivative |
| US4715984A (en) * | 1985-01-22 | 1987-12-29 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid-crystalline dihydroazines |
| JPS63278992A (en) * | 1987-05-12 | 1988-11-16 | Fujitsu Ltd | Phase transition liquid crystal composition |
| US5948551A (en) * | 1994-07-01 | 1999-09-07 | Hoechst Aktiengesellschaft | Use of conjugated compounds containing pyrimidine groups as electroluminescence materials |
| JP2010509781A (en) * | 2006-11-14 | 2010-03-25 | オスラム オプト セミコンダクターズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Novel highly conductive organic charge carrier transport material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0368866B2 (en) | 1991-10-30 |
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