JPS6228137B2 - - Google Patents
Info
- Publication number
- JPS6228137B2 JPS6228137B2 JP58091148A JP9114883A JPS6228137B2 JP S6228137 B2 JPS6228137 B2 JP S6228137B2 JP 58091148 A JP58091148 A JP 58091148A JP 9114883 A JP9114883 A JP 9114883A JP S6228137 B2 JPS6228137 B2 JP S6228137B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- type
- present
- compound
- formula
- 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.)
- Expired
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000005699 fluoropyrimidines Chemical class 0.000 claims description 2
- WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical group FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- IUPPJNKLBCDANR-UHFFFAOYSA-N [amino-[4-(4-fluorophenyl)phenyl]methylidene]azanium chloride Chemical compound [Cl-].C1=CC(C(=N)[NH3+])=CC=C1C1=CC=C(F)C=C1 IUPPJNKLBCDANR-UHFFFAOYSA-N 0.000 description 2
- -1 amidine hydrochloride derivative Chemical class 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical class C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
- FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Description
本発明は液晶混合物の一成分としての新規な化
合物およびそれを含有する液晶組成物に関する。
液晶表示素子は液晶物質が持つ光学異方性およ
び誘電異方性を利用したものであり、その表示様
式によつてTN型（ねじれネマチツク型）、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、それぞれの使用に適する
液晶物質の性質は異なる。いずれの液晶物質も水
分、空気、熱、光等に安定であることが必要であ
る事は共通しており、室温を中心として出来るだ
け広い温度範囲で液晶相を示すものが求められて
いる。
しかしながら、現在のところ、単一化合物では
液晶温度範囲、動作電圧、応答性能等の諸特性に
優れ、実用にできるものはないので、実際には数
種の液晶化合物や非液晶化合物を混合して得られ
る液晶組成物が使用されている。
すなわち、表示素子に使用される液晶組成物に
は、前述した液晶相が実用の温度を含む広い温度
範囲で存在することのほかに、粘度が小さいこ
と、動作の閾電圧が低く小電力で駆動できるこ
と、動作の応答速度が大きいことなどが一般に要
求される。
本発明の目的は、液晶物質に添加してその液晶
組成物の要求されているかかる特性を改善できる
新規な化合物を提供することにある。
本発明の第一は一般式
（式中、Ｒは炭素数１〜８の直鎖アルキル基を
示す。）にて表わされるフルオロピリミジン誘導
体である。
本発明の第二は前記の（）式で表わされるフ
ルオロピリミジン誘導体を含有してなる液晶組成
物である。
本発明によつて提供される化合物は広い液晶温
度範囲を有し、誘電率の正の異方性（△ε＞０、
△ε＝ε−ε⊥、ただし、εは分子の長軸
に、ε⊥は分子の短軸に沿う誘電率を表わす。）
は＋20と公知のフツ素系液晶物質に比べて大きい
ため、これらの化合物を加えた液晶組成物の動作
の閾電圧を低下させることができる。
本発明により提供される化合物は、実用的な液
晶温度範囲を有するが融点が高い為に、この化合
物単独では表示素子用としての実用性はない。し
かし、本発明の化合物は３環を有する液晶物質と
しては粘度が小さく、他の液晶化合物との相溶性
にすぐれ、またその透明点が高い為に他の液晶物
質、例えば、シツフ塩基系、アゾキシ系、安息香
酸フエニルエステル系、シクロヘキサンカルボン
酸フエニルエステル系、シクロヘキサンカルボン
酸シクロヘキシルエステル系、ビフエニル系、フ
エニルシクロヘキサン系、フエニルメタジオキサ
ン系などの液晶の一種類、あるいは数種の系の混
合物と混合させる事により、その透明点を上昇せ
しめる高温液晶成分として有用である。更にま
た、本化合物は屈折率の異方性△ｎが0.24と大き
く本化合物を少量使用することによりコントラス
トの良い表示素子を与えるなど、応答諸特性を向
上させる事ができる。
この様に秀れた特徴を有する本発明の化合物は
下記の反応によつて製造される。
まず、置換ベンゾニトリル（）を出発原料と
して、これにメチルアルコール溶媒中で塩化水素
ガスを反応させてイミドエーテル塩酸塩誘導体
（）を得る。
次に化合物（）にメチルアルコール溶媒中で
アンモニアガスを反応させアミジン塩酸塩誘導体
（）を得る。この化合物（）とアクロレイン
誘導体（）を適当な塩基触媒（例えば金属アル
コラート、水酸化ナトリウム、１，８−ジアザビ
シクロ〔５，４，０〕−７−ウンデセン等）の存
在下にて縮合環化反応を行い、目的の化合物
（）を得る。
以下実施例により、本発明を詳細に説明する
が、本発明はこれらの実施例に限定されるもので
はない。
実施例 １
５−プロピル−２−（4′−フルオロビフエニリ
ル−４）−ピリミジンの製造
20mlの無水メタノール中に2.8ｇ（0.12モル）
のナトリウムを溶解したナトリウムメチラート溶
液を撹拌して、15.1ｇ（0.06モル）の４−（4′−フ
ルオロフエニル）ベンズアミジン塩酸塩および
9.2ｇ（0.066モル）のα−プロピル−β−ジメチ
ルアミノアクロレインを加えた。この際、撹拌を
続けながら加熱還流下に６時間反応させた。反応
終了後、常圧にてメタノールを溜去し、残液にト
ルエン20mlを加えて生成物を抽出した。抽出液は
水洗後、無水硫酸ナトリウムにて乾燥した。これ
からトルエンを溜去して残つた固形物を10mlの酢
酸エチル溶媒から再結晶して、目的の５−プロピ
ル−２−（4′−フルオロビフエニリル−４）ピリ
ミジン10.9ｇを得た。このものの転移温度は、Ｃ
−Ｎ点が96.9℃、Ｎ−Ｉ点が177.4℃であり、ま
た合成の収率は62％であつた。
実施例 ２〜６
実施例１におけるα−プロピル−β−ジメチル
アミノアクロレインに代えて、α−位にそれぞれ
エチル基、ブチル基、ペンチル基、ヘキシル基ま
たはヘプチル基をもつα−アルキル−β−ジメチ
ルアミノアクロレインを用いたほかは実施例１と
同様にして、それぞれの置換アルキル基を有する
５−アルキル−２−（4′−フルオロビフエニリル
−４）−ピリミジンを製造した。これらの転移温
度を実施例１の結果とともに第１表に示す。
The present invention relates to novel compounds as a component of liquid crystal mixtures and to liquid crystal compositions containing them. Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and are divided into TN type (twisted nematic type), DS type (dynamic scattering type), and guest/host type depending on the display format. There are various types of liquid crystals, such as type and DAP type, and the properties of the liquid crystal materials suitable for each type of use are different. All liquid crystal materials have in common that they must be stable against moisture, air, heat, light, etc., and there is a demand for materials that exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature. However, at present, there is no single compound that has excellent properties such as liquid crystal temperature range, operating voltage, and response performance, and can be put to practical use. The resulting liquid crystal composition is used. In other words, in addition to the fact that the liquid crystal composition used in display elements has the above-mentioned liquid crystal phase in a wide temperature range including practical temperatures, it also has a low viscosity, a low operating threshold voltage, and can be driven with low power. In general, it is required to have high operational response speed. It is an object of the present invention to provide new compounds which can be added to liquid crystal materials to improve such desired properties of the liquid crystal compositions. The first aspect of the present invention is the general formula (In the formula, R represents a straight chain alkyl group having 1 to 8 carbon atoms.) The second aspect of the present invention is a liquid crystal composition containing a fluoropyrimidine derivative represented by the above formula (). The compound provided by the present invention has a wide liquid crystal temperature range and has positive anisotropy of dielectric constant (△ε>0,
Δε=ε−ε⊥, where ε represents the dielectric constant along the long axis of the molecule, and ε⊥ represents the dielectric constant along the short axis of the molecule. )
is +20, which is larger than that of known fluorine-based liquid crystal substances, so the operating threshold voltage of liquid crystal compositions containing these compounds can be lowered. Although the compound provided by the present invention has a practical liquid crystal temperature range, since it has a high melting point, this compound alone is not practical for use in display devices. However, the compound of the present invention has a low viscosity for a three-ring liquid crystal substance, has excellent compatibility with other liquid crystal compounds, and has a high clearing point, so it cannot be used with other liquid crystal substances, such as Schiff base type, azoxy One type of liquid crystal, such as benzoic acid phenyl ester type, cyclohexanecarboxylic acid phenyl ester type, cyclohexanecarboxylic acid cyclohexyl ester type, biphenyl type, phenylcyclohexane type, phenylmetadioxane type, or several types of liquid crystals. It is useful as a high-temperature liquid crystal component that increases the clearing point when mixed with a mixture. Furthermore, this compound has a large refractive index anisotropy Δn of 0.24, and by using a small amount of this compound, various response characteristics can be improved, such as providing a display element with good contrast. The compound of the present invention having such excellent characteristics can be produced by the following reaction. First, substituted benzonitrile () is used as a starting material, and hydrogen chloride gas is reacted with it in a methyl alcohol solvent to obtain an imidoether hydrochloride derivative (). Next, the compound () is reacted with ammonia gas in a methyl alcohol solvent to obtain an amidine hydrochloride derivative (). This compound () and the acrolein derivative () are subjected to a condensation cyclization reaction in the presence of an appropriate base catalyst (e.g., metal alcoholate, sodium hydroxide, 1,8-diazabicyclo[5,4,0]-7-undecene, etc.) to obtain the desired compound (). EXAMPLES The present invention will be described in detail below with reference to Examples, but the present invention is not limited to these Examples. Example 1 Preparation of 5-propyl-2-(4'-fluorobiphenyl-4)-pyrimidine 2.8 g (0.12 mol) in 20 ml of absolute methanol
of sodium methylate was stirred to dissolve 15.1 g (0.06 mol) of 4-(4'-fluorophenyl)benzamidine hydrochloride and
9.2 g (0.066 mol) of α-propyl-β-dimethylaminoacrolein was added. At this time, the reaction was continued under heating and reflux for 6 hours while stirring. After the reaction was completed, methanol was distilled off at normal pressure, and 20 ml of toluene was added to the residual liquid to extract the product. The extract was washed with water and then dried over anhydrous sodium sulfate. Toluene was distilled off, and the remaining solid was recrystallized from 10 ml of ethyl acetate solvent to obtain 10.9 g of the desired 5-propyl-2-(4'-fluorobiphenyl-4)pyrimidine. The transition temperature of this substance is C
-N point was 96.9°C, N-I point was 177.4°C, and the synthesis yield was 62%. Examples 2 to 6 α-alkyl-β-dimethyl having an ethyl group, butyl group, pentyl group, hexyl group, or heptyl group at the α-position, respectively, in place of α-propyl-β-dimethylaminoacrolein in Example 1 5-alkyl-2-(4'-fluorobiphenyl-4)-pyrimidine having each substituted alkyl group was produced in the same manner as in Example 1 except that aminoacrolein was used. These transition temperatures are shown in Table 1 together with the results of Example 1.
【表】
実施例７ （応用例）
次の３種の液晶物質
トランス−４−プロピル−（4′−シアノフエニ
ル）シクロヘキサン 30重量％
トランス−４−ペンチル−（4′−シアノフエニ
ル）シクロヘキサン 40重量％
トランス−４−ヘプチル−（4′−シアノフエニ
ル）シクロヘキサン 30重量％
からなる液晶組成物のＮ−Ｉ転移点は52.1℃であ
り、20℃における粘度（η20と略す）は23.4cP、
△εは11.7であつた。これをセル厚10μｍのTN
セルに封入したものの動作閾電圧は1.55V、飽和
電圧は2.15Vであつた。
上記の液晶組成物85重量部に本発明の化合物の
一つである実施例１で製造した５−プロピル−２
−（4′−フルオロビフエニリル−４）ピリミジン
15重量部を加えたネマチツク液晶組成物の相転移
点を観測したところ、Ｎ−Ｉ点は65℃また、この
物のη20は26.3cP、△εは12.2であつた。該液晶
組成物を前記のTNセルに封入した素子の動作閾
電圧は1.41V、飽和電圧は1.9Vであつた。
これは本発明の化合物の添加により、透明点の
上昇および動作電圧の低下がもたらされたことを
示している。
比較例 １〜３
実施例１における４−（4′−フルオロフエニ
ル）ベンズアミジン塩酸塩に代えて４−（4′−ク
ロロフエニル）ベンズアミジン塩酸塩を用い、他
方の原料としてα−位にそれぞれエチル基、プロ
ピル基およびブチル基をもつα−アルキル−β−
ジメチルアミノアクロレインを用いて実施例１と
同様にして、それぞれの置換アルキル基を有する
５−アルキル−２−（4′−クロロビフエニリル−
４）−ピリミジンを製造した。これらの化合物お
よびその相転移温度を以下に示す。
５−エチル−２−（4′−クロロビフエニリル−
４）−ピリミジン
５−プロピル−２−（4′−クロロビフエニリル−
４）−ピリミジン
５−ブチル−２−（4′−クロロビフエニリル−
４）−ピリミジン
比較例 ４
実施例７で用いた、３種のトランス−４−アル
キル−（4′−シアノフエニル）シクロヘキサンか
らなる液晶組成物85重量部に比較例１に示す５−
エチル−２−（4′−クロロビフエニリル−４）−ピ
リミジン15重量部を混合して液晶組成物を調製し
た。この液晶組成物のη20は27.1cP、△εは13.6
であつた。また実施例７と同様にしてこの液晶組
成物を用いて作成したTNセルのしきい値電圧は
1.59Vであつた。[Table] Example 7 (Application example) The following three liquid crystal substances Trans-4-propyl-(4'-cyanophenyl)cyclohexane 30% by weight Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 40% by weight Trans The N-I transition point of a liquid crystal composition consisting of 30% by weight of -4-heptyl-(4'-cyanophenyl)cyclohexane is 52.1°C, and the viscosity (abbreviated as η 20 ) at 20°C is 23.4cP.
Δε was 11.7. This is TN with a cell thickness of 10 μm.
When sealed in a cell, the operating threshold voltage was 1.55V and the saturation voltage was 2.15V. 5-propyl-2 prepared in Example 1, which is one of the compounds of the present invention, was added to 85 parts by weight of the above liquid crystal composition.
-(4'-fluorobiphenyl-4)pyrimidine
When the phase transition point of the nematic liquid crystal composition to which 15 parts by weight was added was observed, the N-I point was 65°C, the η 20 of this material was 26.3 cP, and the Δε was 12.2. The operating threshold voltage of the device in which the liquid crystal composition was sealed in the TN cell was 1.41V, and the saturation voltage was 1.9V. This indicates that the addition of the compounds of the present invention resulted in an increase in the clearing point and a decrease in the operating voltage. Comparative Examples 1 to 3 4-(4'-chlorophenyl)benzamidine hydrochloride was used in place of 4-(4'-fluorophenyl)benzamidine hydrochloride in Example 1, and an ethyl group was added at the α-position as the other raw material. , α-alkyl-β- with propyl and butyl groups
In the same manner as in Example 1 using dimethylaminoacrolein, 5-alkyl-2-(4'-chlorobiphenylyl-
4)-pyrimidine was produced. These compounds and their phase transition temperatures are shown below. 5-ethyl-2-(4'-chlorobiphenylyl-
4)-pyrimidine 5-propyl-2-(4'-chlorobiphenylyl-
4)-pyrimidine 5-Butyl-2-(4'-chlorobiphenylyl-
4)-pyrimidine Comparative Example 4 85 parts by weight of the liquid crystal composition composed of three types of trans-4-alkyl-(4'-cyanophenyl)cyclohexane used in Example 7 was added with the 5-
A liquid crystal composition was prepared by mixing 15 parts by weight of ethyl-2-(4'-chlorobiphenylyl-4)-pyrimidine. The η 20 of this liquid crystal composition is 27.1 cP, and the Δε is 13.6.
It was hot. In addition, the threshold voltage of a TN cell prepared using this liquid crystal composition in the same manner as in Example 7 was
It was 1.59V.
Claims (1)
示す。）にて表わされるフルオロピリミジン誘導
体。 ２ 一般式 （式中、Ｒは炭素数１〜８の直鎖アルキル基を
示す。）にて表わされるフルオロピリミジン誘導
体を少くとも１種含有してなる液晶組成物。[Claims] 1. General formula (In the formula, R represents a straight-chain alkyl group having 1 to 8 carbon atoms.) A fluoropyrimidine derivative represented by the formula: 2 General formula (In the formula, R represents a straight-chain alkyl group having 1 to 8 carbon atoms.) A liquid crystal composition containing at least one fluoropyrimidine derivative represented by the following formula.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9114883A JPS59216876A (en) | 1983-05-24 | 1983-05-24 | Halogenopyrimidine derivative |
| US06/593,434 US4581155A (en) | 1983-03-31 | 1984-03-26 | Halogenopyrimidine derivatives |
| EP84103419A EP0123907B1 (en) | 1983-03-31 | 1984-03-28 | Fluoropyrimidine derivatives |
| DE8484103419T DE3479120D1 (en) | 1983-03-31 | 1984-03-28 | Fluoropyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9114883A JPS59216876A (en) | 1983-05-24 | 1983-05-24 | Halogenopyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59216876A JPS59216876A (en) | 1984-12-06 |
| JPS6228137B2 true JPS6228137B2 (en) | 1987-06-18 |
Family
ID=14018438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9114883A Granted JPS59216876A (en) | 1983-03-31 | 1983-05-24 | Halogenopyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59216876A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3270906D1 (en) * | 1982-01-14 | 1986-06-05 | Merck Patent Gmbh | Liquid crystal mixtures |
| DE3315295A1 (en) * | 1983-04-27 | 1984-10-31 | Merck Patent Gmbh, 6100 Darmstadt | FLUORINE PYRIMID DERIVATIVES |
| JPS61197563A (en) * | 1985-02-27 | 1986-09-01 | Chisso Corp | Pyrimidine derivative having trifluoromethylphenyl group |
| JPH0825957B2 (en) * | 1985-03-12 | 1996-03-13 | チッソ株式会社 | Difluoro aromatic compound |
| JPH0781141B2 (en) * | 1986-01-20 | 1995-08-30 | チッソ株式会社 | Nematic liquid crystal composition |
| US4640795A (en) * | 1986-03-21 | 1987-02-03 | Chisso Corporation | 5-alkyl-2-(3,4-difluorophenyl)pyrimidine and nematic liquid crystal composition containing same |
| JP2796753B2 (en) * | 1990-05-09 | 1998-09-10 | キヤノン株式会社 | Chiral smectic liquid crystal composition and liquid crystal device using the same |
| JP4935055B2 (en) | 2005-11-15 | 2012-05-23 | Ｊｎｃ株式会社 | Liquid crystal composition and liquid crystal display element |
| EP1788064B1 (en) * | 2005-11-16 | 2009-03-11 | Chisso Corporation | Liquid crystal composition and liquid crystal display device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5239685A (en) * | 1975-09-19 | 1977-03-28 | Hoffmann La Roche | Pyrimidine derivatives preparation method and nematic mixture |
-
1983
- 1983-05-24 JP JP9114883A patent/JPS59216876A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5239685A (en) * | 1975-09-19 | 1977-03-28 | Hoffmann La Roche | Pyrimidine derivatives preparation method and nematic mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59216876A (en) | 1984-12-06 |
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