JPS62267284A - Pyrimidinylphenyldioxane compound - Google Patents
Pyrimidinylphenyldioxane compoundInfo
- Publication number
- JPS62267284A JPS62267284A JP11019486A JP11019486A JPS62267284A JP S62267284 A JPS62267284 A JP S62267284A JP 11019486 A JP11019486 A JP 11019486A JP 11019486 A JP11019486 A JP 11019486A JP S62267284 A JPS62267284 A JP S62267284A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- liquid crystal
- formula
- alkyl
- trans
- 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
- -1 Pyrimidinylphenyldioxane compound Chemical class 0.000 title abstract description 6
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 2
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical class Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- 210000004460 N cell Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［発明の目的］
本発明は、新規な液晶性化合物および該化合物を含有す
る液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Object of the Invention] The present invention relates to a novel liquid crystal compound and a liquid crystal composition containing the compound.
液晶物質およびその組成物は、その液晶相における誘電
率の異方性（Δεと略記する）および光の屈折率の異方
性（△ｎと略記する）を利用して種々の表示装置に使用
され、その表示方式にはＴＮ型（ねじれマチック型）、
ＤＳ型（動的散乱型）、ゲスト・ホスト型、ＤＡＰ型な
ど各種の方式に分けられる。これらに用いる液晶材料は
単独ではその表示素子の緒特性すなわち液晶温度範囲、
動作電圧、応答性能などで実用的な使用に耐えるものが
なく、実用的には数種の液晶化合物あるいは液晶化合物
に非液晶化合物を混合して用いられる。Liquid crystal substances and compositions thereof are used in various display devices by utilizing the anisotropy of dielectric constant (abbreviated as Δε) and the anisotropy of optical refractive index (abbreviated as Δn) in the liquid crystal phase. The display methods include TN type (twist matic type),
It can be divided into various types such as DS type (dynamic scattering type), guest-host type, and DAP type. The liquid crystal materials used in these devices alone have the characteristics of the display element, that is, the liquid crystal temperature range,
There is no one that can withstand practical use in terms of operating voltage, response performance, etc., and for practical purposes, several types of liquid crystal compounds or a mixture of a liquid crystal compound and a non-liquid crystal compound are used.
本発明の目的は、液晶組成物の成分に用いることにより
、表示素子の緒特性を向上できる化合物および該化合物
を含有する液晶組成物を提供することである。An object of the present invention is to provide a compound that can improve the performance characteristics of a display element when used as a component of a liquid crystal composition, and a liquid crystal composition containing the compound.
［発明の構成］
本発明は、一般式
（式中、Ｒ１、Ｒ２は、それぞれ独立に炭素数１〜１２
のアルキル基を示す。）
で表わされるトランス−２−（４−（５−アルキルヒリ
ミシニル−２）フェニル）−５−アルキル−１，３−ジ
オキサン化合物および該化合物を含有する液晶組成物で
ある。[Structure of the Invention] The present invention is based on the general formula (wherein R1 and R2 each independently have 1 to 12 carbon atoms)
represents an alkyl group. ) A trans-2-(4-(5-alkylhyrimicinyl-2)phenyl)-5-alkyl-1,3-dioxane compound and a liquid crystal composition containing the compound.
本発明の化合物の製造法の一例を示すと下記の反応式の
ようになる。An example of the method for producing the compound of the present invention is shown in the following reaction formula.
（式中、Ｒ，、Ｒ２は、それぞれ独立に炭素数１〜１２
のアルキル基を示す。）
まず、ｐ−置換ベンゾニトリル（ＩＩ）をエタノール中
で塩化水素ガスおよびエタノールと反応させてｐ−置換
ベンズイミデート塩酸塩（Ｉｌｌ）を得る。(In the formula, R,, R2 each independently have a carbon number of 1 to 12
represents an alkyl group. ) First, p-substituted benzonitrile (II) is reacted with hydrogen chloride gas and ethanol in ethanol to obtain p-substituted benzimidate hydrochloride (Ill).
次にこの化合物（１）をアルコール溶媒中でアンモニア
ガスと反応させて、ｐ−置換ペンズアミジ／塩酸塩（Ｉ
Ｖ）を得る。Next, this compound (1) was reacted with ammonia gas in an alcohol solvent, and p-substituted penzamidi/hydrochloride (I
V) is obtained.
次に化合物＋ＩＶ）とα−アルキル−β−ジメチルアミ
ノアクロレイン（■とを適当な塩基触媒の存在下に縮合
環化反応を行わせて目的の化合物（１）を得る。塩基触
媒としては、アルカリ金属アルコラード、水酸化ナトリ
ウム、１，８−ジアザビシクロ（５，４，０）−ウンデ
センなどを用いることができる。Next, compound +IV) and α-alkyl-β-dimethylaminoacrolein (■) are subjected to a condensation cyclization reaction in the presence of an appropriate base catalyst to obtain the target compound (1).As the base catalyst, an alkali Metal alcoholades, sodium hydroxide, 1,8-diazabicyclo(5,4,0)-undecene, and the like can be used.
本発明の化合物は、比較的高い温度域に巾広いネマチッ
ク相を有する液晶性化合物である。The compound of the present invention is a liquid crystalline compound having a wide nematic phase in a relatively high temperature range.
該化合物は３個の６員環を有する化合物としては粘度が
小さく、また、ほかの既存の液晶性化合物例えばエステ
ル系、シック塩基系、アゾキシ系、ビフェニル系、シク
ロヘキサン系、ヒリ・ジン系、ピリミジン系などの液晶
化合物との相溶性が良い。該化合物は熱、光、電気、空
気や水分などに対しても安定であり、液晶相において無
色である。The compound has a low viscosity for a compound having three 6-membered rings, and is compatible with other existing liquid crystal compounds such as esters, thick bases, azoxys, biphenyls, cyclohexanes, pyridines, and pyrimidines. Good compatibility with liquid crystal compounds such as The compound is stable against heat, light, electricity, air and moisture, and is colorless in the liquid crystal phase.
本発明の化合物の液晶相における誘電率異方性（以下Δ
εと略記する）は正であり、光の屈折率の異方性値（以
下△ｎと略記する）も大きい。Dielectric anisotropy (hereinafter Δ) in the liquid crystal phase of the compound of the present invention
(abbreviated as ε) is positive, and the anisotropy value of the refractive index of light (hereinafter abbreviated as Δn) is also large.
従って上に述べた本発明の化合物の特性を利用して、該
化合物を成分として既存の液晶物質に混合することによ
り、各種の液晶表示素子用に適した液晶組成物を構成す
ることができる。Therefore, by utilizing the above-mentioned properties of the compound of the present invention and mixing the compound as a component with existing liquid crystal materials, it is possible to construct a liquid crystal composition suitable for various liquid crystal display devices.
例えば、ＴＮ型表示素子用液晶組成物の成分として本発
明の化合物を用いると、組成物の粘度をさほど上昇させ
ることなく、また表示素子の駆動電圧も殆んど上昇させ
ずに、表示素子の使用温度範囲を高温側に拡張すること
ができる。For example, when the compound of the present invention is used as a component of a liquid crystal composition for a TN type display element, the viscosity of the composition does not increase significantly, and the driving voltage of the display element hardly increases. The operating temperature range can be extended to the high temperature side.
本発明の液晶組成物においては（１）式で表わされる化
合物のほかに、低温度域に液晶相を有する成分を含有さ
せて実用の温度領域を広くすることが望ましい。In addition to the compound represented by formula (1), the liquid crystal composition of the present invention preferably contains a component having a liquid crystal phase in a low temperature range to widen the practical temperature range.
［実施例］
以下に実施例により本発明の詳細な説明するが、本発明
はこれらの実施例に限られるものではない。[Examples] The present invention will be described in detail below with reference to Examples, but the present invention is not limited to these Examples.
実施例１
トランス−２−（４−（５−エチルピリミジニル−２）
フェニル）−５−プロピル−１，３−ジオキサン
４−（トランス−５−プロピル−１，３−ジオキサニル
＝２）ベンズアミジン塩１１１塩５．０．９（０，０１
８ｍｏｌ ）とα−エチル−β−ジメチルアミノアクロ
レイン２．２ 、！ｉ’ （０，０１８ｍｏｌ ）をナ
トリウムメチラート１．４ 、！ｉ’ （０，０２６ｍ
ｏｌ ）を無水メタノール５０ＷＬｌに溶解したナトリ
ウムメチラート溶液に加えた。ついで撹拌しながら２時
間煮沸した後にメタノールを留去した。反応残渣に水１
００ｍｊ！とトルエン１００ｍ１を加え生成物を抽出し
、抽出液を水洗後、無水硫酸す） ＩＪウムにてトルエ
ン層を乾燥し、その後にトルエンを留去して残った固形
物をエタノールで再結晶を３回行なって目的のトランス
−２−（４−（５−エチルピリミジニル−２）フェニル
）−５−プロピル−１，３−ジオキサン３．９ 、！９
（０，０１２ｍｏｌ）を得た。Example 1 trans-2-(4-(5-ethylpyrimidinyl-2)
phenyl)-5-propyl-1,3-dioxane 4-(trans-5-propyl-1,3-dioxanyl=2)benzamidine salt 111 salt 5.0.9 (0,01
8 mol) and α-ethyl-β-dimethylaminoacrolein 2.2,! i' (0,018 mol) to sodium methylate 1.4,! i' (0,026m
ol) was added to a solution of sodium methylate dissolved in 50 WLl of absolute methanol. The mixture was then boiled for 2 hours with stirring, and then methanol was distilled off. 1 part water to the reaction residue
00mj! and 100 ml of toluene were added to extract the product, and the extract was washed with water and then diluted with anhydrous sulfuric acid.) The toluene layer was dried with IJum, and then the toluene was distilled off, and the remaining solid was recrystallized with ethanol. Repeat to obtain the desired trans-2-(4-(5-ethylpyrimidinyl-2)phenyl)-5-propyl-1,3-dioxane 3.9 times! 9
(0,012 mol) was obtained.
この化合物の元素分析値は次の如く、理論値とよく一致
した。The elemental analysis values of this compound were in good agreement with the theoretical values as shown below.
またこの化合物のＣＮ点は１２８℃、ＮＩ点は１８０℃
であった。Also, the CN point of this compound is 128°C, and the NI point is 180°C.
Met.
実施例２〜６
実施例１に準じた方法で合成した化合物とその物性値を
実施例１の結果とともに表１に示す。Examples 2 to 6 Compounds synthesized by a method similar to Example 1 and their physical property values are shown in Table 1 together with the results of Example 1.
表１の相転移点の欄において、Ｃは結晶相、Ｎはネマチ
ック相、■は等方性液体相を示す。In the phase transition point column of Table 1, C indicates a crystalline phase, N indicates a nematic phase, and ■ indicates an isotropic liquid phase.
表１におけるΔｎ１Δεおよび２０℃における粘度η２
ｏハフェニルシクロヘキサン系液晶組成物との混合系の
物性値から外挿法により求めた値である。Δn1Δε and viscosity η2 at 20°C in Table 1
o This is a value determined by extrapolation from the physical property values of the mixed system with the haphenylcyclohexane liquid crystal composition.
実施例７ （使用例１）
からなる液晶組成物置のＮＩ点は、５２．１ ’Ｃ１Ｔ
Ｎセルに封入したもののしきい値電圧は１．５４ｖ１飽
和電圧は２．１３Ｖであり、八〇は０．１１９（’ｅ＝
１．６０９、’ｏ＝１．４９０）であった。Example 7 (Usage Example 1) The NI point of the liquid crystal composition storage is 52.1'C1T
The threshold voltage of the sealed N cell is 1.54v1, the saturation voltage is 2.13V, and 80 is 0.119 ('e=
1.609,'o=1.490).
該液晶組成物置８５重量部に本発明の実施例１に示す化
合物トランス−２−（４−（５−エチルピリミジニル−
２）フェニル）−５−プロピル−１，３−ジオキサンを
１５重量部加えた液晶組成物のＮＩ点は、６９０℃と上
昇し、η２ｏは２７、１ ｃＰとわずかに上昇した。ま
た、この組成物を前述のＴＮセルに封入したしきい値電
圧は１．５８Ｖ、飽和電圧は２．１６Ｖとほとんど変化
しなかった。さらに△ｎは０．１２８ （ｎｅ ＝１．
６２１１ｎｏ−１，４９３）と上昇した。The compound trans-2-(4-(5-ethylpyrimidinyl-) shown in Example 1 of the present invention was added to 85 parts by weight of the liquid crystal composition.
2) The NI point of the liquid crystal composition to which 15 parts by weight of phenyl)-5-propyl-1,3-dioxane was added rose to 690°C, and the η2o rose slightly to 27.1 cP. Further, when this composition was sealed in the aforementioned TN cell, the threshold voltage was 1.58V, and the saturation voltage was 2.16V, which were almost unchanged. Furthermore, Δn is 0.128 (ne = 1.
6211no-1, 493).
［発明の効果コ
前述したように本発明によって提供されるトランス−２
−（４−（５−アルキルピリミジニル−２）フェニル）
−５−アルキル−１，３−ジオキサン化合物はディスプ
レイ用の液晶材料として有用である。[Effects of the Invention] As described above, the transformer-2 provided by the present invention
-(4-(5-alkylpyrimidinyl-2)phenyl)
-5-alkyl-1,3-dioxane compounds are useful as liquid crystal materials for displays.
また、かかる新規物質が液晶成分として提供されること
によって液晶材料の選択の範囲が広くなるという利点も
生れた。Further, by providing such a new substance as a liquid crystal component, there is an advantage that the range of selection of liquid crystal materials is widened.
以上that's all
Claims (2)
１２のアルキル基を示す。） で表わされるトランス−２−｛４−（５−アルキルピリ
ミジニル−２）フェニル｝−５−アルキル−１，３−ジ
オキサン化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 each independently have a carbon number of 1 to
12 alkyl groups are shown. ) trans-2-{4-(5-alkylpyrimidinyl-2)phenyl}-5-alkyl-1,3-dioxane compound.
１２のアルキル基を示す。） で表わされるトランス−２−｛４−（５−アルキルピリ
ミジニル−２）フェニル｝−５−アルキル−１，３−ジ
オキサン化合物を含有する液晶組成物。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 each independently have a carbon number of 1 to
12 alkyl groups are shown. ) A liquid crystal composition containing a trans-2-{4-(5-alkylpyrimidinyl-2)phenyl}-5-alkyl-1,3-dioxane compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11019486A JPS62267284A (en) | 1986-05-14 | 1986-05-14 | Pyrimidinylphenyldioxane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11019486A JPS62267284A (en) | 1986-05-14 | 1986-05-14 | Pyrimidinylphenyldioxane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62267284A true JPS62267284A (en) | 1987-11-19 |
| JPH046712B2 JPH046712B2 (en) | 1992-02-06 |
Family
ID=14529432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11019486A Granted JPS62267284A (en) | 1986-05-14 | 1986-05-14 | Pyrimidinylphenyldioxane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62267284A (en) |
-
1986
- 1986-05-14 JP JP11019486A patent/JPS62267284A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH046712B2 (en) | 1992-02-06 |
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