JPH0629262B2 - Pyrimidine derivative - Google Patents
Pyrimidine derivativeInfo
- Publication number
- JPH0629262B2 JPH0629262B2 JP1173511A JP17351189A JPH0629262B2 JP H0629262 B2 JPH0629262 B2 JP H0629262B2 JP 1173511 A JP1173511 A JP 1173511A JP 17351189 A JP17351189 A JP 17351189A JP H0629262 B2 JPH0629262 B2 JP H0629262B2
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- liquid crystal
- compound
- chloroform
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は電気光学的表示材料として用いられる新規なピ
リミジン誘導体に関する。The present invention relates to a novel pyrimidine derivative used as an electro-optical display material.
本発明は一般式 （上式中、Ｒは炭素原子数が１〜１０の直鎖アルキル基
を示す） で表わされる新規な化合物である。また本発明の化合物
は誘電率の異方性（以下Δεという）が正で非常に大き
いという特徴を有する。したがって本発明の化合物
（１）と他の液晶化合物を混合した液晶組成物を用いる
ことにより駆動電圧が非常に低い液晶表示装置を提供す
ることができる。The present invention has the general formula (In the above formula, R represents a linear alkyl group having 1 to 10 carbon atoms). Further, the compound of the present invention has a feature that the anisotropy of dielectric constant (hereinafter referred to as Δε) is positive and very large. Therefore, by using a liquid crystal composition in which the compound (1) of the present invention is mixed with another liquid crystal compound, a liquid crystal display device having a very low driving voltage can be provided.
液晶表示装置は液晶の持つ電気光学効果を利用したもの
であり、これに用いられる液晶相にはネマチック相、コ
レステリック相、スメクチック相がある。そして現在最
も広く用いられる表示方式はネマチック相を利用したね
じれネマチック（以下ＴＮという）型である。The liquid crystal display device utilizes the electro-optical effect of liquid crystal, and the liquid crystal phase used for the liquid crystal display device has a nematic phase, a cholesteric phase, and a smectic phase. The currently most widely used display method is a twisted nematic (hereinafter referred to as TN) type that utilizes a nematic phase.
液晶表示装置は、 １．小型でしかも薄くできる。The liquid crystal display device is 1. It is small and can be made thin.
２．駆動電圧が低く、かつ消費電力が小さい。2. Low drive voltage and low power consumption.
３．受光素子であるため長時間使用しても目が疲れな
い。3. Since it is a light-receiving element, it will not tire your eyes even if you use it for a long time.
等の長所を持つことから、従来よりウォッチ、電卓、オ
ーディオ機器、各種計測機、自動車のダッシュボード等
に応用されている。特に最近ではパーソナルコンピュー
タやワードプロセッサーのディスプレイさらには白黒ま
たはカラーのポケットテレビなどの画素数の大変多い表
示にも応用され、ＣＲＴに代わる表示装置として注目を
集めている。このように液晶表示装置は多方面に応用さ
れており、今後さらにその応用分野は拡大していくと考
えられる。これに伴ない液晶材料に要求される特性も変
化していくと思われるが、以下に示した特性は基本的な
もので必要不可欠である。Since it has advantages such as, it has been applied to watches, calculators, audio devices, various measuring instruments, automobile dashboards, etc. In particular, recently, it has been applied to a display of a personal computer or a word processor, and also to a display with a very large number of pixels such as a black and white or color pocket TV, and has been attracting attention as a display device replacing the CRT. As described above, the liquid crystal display device is applied in various fields, and its application field is expected to further expand in the future. The characteristics required for liquid crystal materials are expected to change along with this, but the characteristics shown below are basic and indispensable.
１．着色がなく、熱、光、電気的、化学的に安定である
こと。1. It has no color and is stable to heat, light, electricity, and chemicals.
２．実用温度範囲が広いこと。2. Wide operating temperature range.
３．電気光学的な応答速度が速いこと。3. High electro-optical response speed.
４．駆動電圧が低いこと。4. Low drive voltage.
５．電圧−光透過率特性の立ち上がりが急峻であり、ま
たそのしきい値電圧（以下Ｖｔｈという）の温度依存性
が小さいこと。5. The voltage-light transmittance characteristic has a steep rise, and its threshold voltage (hereinafter referred to as V th ) has little temperature dependence.
６．視角範囲が広いこと。6. Wide viewing angle range.
これらの特性のうち、１の特性を満足する液晶は数多く
知られているが、２以下の特性を単一成分で満足させる
液晶化合物は知られていない。そこでこれらの特性を得
るために数種類のネマチック液晶化合物または非液晶化
合物を混合した液晶組成物を用いている。このうちで４
の特性を満足させるためには、しきい値電圧を下げなけ
ればいけないが、Ｖｔｈと弾性定数（以下Ｋという）と
Δεとの間には次の関係があり、Ｖｔｈを下げるには Ｖｔｈ∝（Ｋ／Δε）1/2 Δεが大きく、Ｋが小さい液晶化合物が必要になる。Many liquid crystals satisfying one of these characteristics are known, but no liquid crystal compound satisfying the characteristics of 2 or less with a single component is known. Therefore, in order to obtain these characteristics, a liquid crystal composition in which several kinds of nematic liquid crystal compounds or non-liquid crystal compounds are mixed is used. 4 of these
To satisfy the characteristics, but do need to lower the threshold voltage, the following relationship between Δε and V th and the elastic constant (hereinafter referred to as K), to lower the V th V A liquid crystal compound having a large th ∝ (K / Δε) 1/2 Δε and a small K is required.
そこで本発明はこのような実情における要請に応じるも
のであり、その目的は他の一種または２種以上のネマチ
ック液晶化合物または非液晶化合物と混合することによ
り、しきい値電圧の低い液晶組成物を得ることができる
新規な液晶化合物を提供することである。Therefore, the present invention responds to the demands in such an actual situation, and an object thereof is to prepare a liquid crystal composition having a low threshold voltage by mixing with one or more kinds of nematic liquid crystal compounds or non-liquid crystal compounds. It is to provide a novel liquid crystal compound that can be obtained.
本発明は一般式 （上式中、Ｒは炭素原子数が１〜１０の直鎖アルキル基
を示す） で表される新規な液晶化合物である。The present invention has the general formula (In the above formula, R represents a linear alkyl group having 1 to 10 carbon atoms) and is a novel liquid crystal compound.
本発明の化合物（１）は次の製造方法により得ることが
できる。The compound (1) of the present invention can be obtained by the following production method.
工程１）化合物（２）をクロロホルム中で臭素と反応さ
せて化合物（３）を得る。Step 1) Compound (2) is reacted with bromine in chloroform to obtain compound (3).
工程２）化合物（３）をＮ−メチルピロリドン中でシア
ン化第一銅と反応させて化合物（４）を得る。Step 2) Compound (3) is reacted with cuprous cyanide in N-methylpyrrolidone to obtain compound (4).
工程３）化合物（４）を酢酸中で亜硝酸ナトリウムと硫
酸で反応させジアゾニウム塩にした後、臭化水素酸中で
臭化第一銅と反応させて化合物（５）を得る。Step 3) Compound (4) is reacted with sodium nitrite and sulfuric acid in acetic acid to form a diazonium salt, and then reacted with cuprous bromide in hydrobromic acid to obtain compound (5).
工程４）化合物（５）をエタノールとベンゼンの混合溶
媒中で乾燥塩化水素ガスと反応させる。溶媒を留去し、
得られた結晶をエタノール中で乾燥アンモニアガスと反
応させ化合物（６）を得る。Step 4) Compound (5) is reacted with dry hydrogen chloride gas in a mixed solvent of ethanol and benzene. Evaporate the solvent,
The obtained crystals are reacted with dry ammonia gas in ethanol to obtain the compound (6).
工程５）化合物（６）と化合物（７）をエタノール中で
金属ナトリウムで反応させて化合物（８）を得る。Step 5) Compound (6) and compound (7) are reacted with metallic sodium in ethanol to obtain compound (8).
工程６）化合物（８）をＮ−メチルピロリドン中でシア
ン化第一銅と反応させて化合物（１）を得る。Step 6) Compound (8) is reacted with cuprous cyanide in N-methylpyrrolidone to obtain compound (1).
〔実施例〕 以下、実施例と応用例により本発明をさらに詳しく説明
する。 [Examples] Hereinafter, the present invention will be described in more detail with reference to examples and application examples.
実施例１ ２−（３′，５′−ジフルオロ−４′−シアノフェニ
ル）−５−ペンチルピリミジンの製造 工程１）クロロホルム４００ｍ中へ２，６−ジフルオ
ロアニリン２３１ｇを溶かし、その中へ臭素３００ｇを
滴下した。１時間還流後、反応液を１０％水酸化カリウ
ム溶液中へ注いだ。それをクロロホルムで抽出し、有機
層を１０％水酸化カリウム溶液と水で洗浄した。クロロ
ホルムを留去後減圧蒸留を行ない（ｂｐ７０〜８０℃／
４mmHg）ヘキサン中より再結晶し、４−ブロモ−２，６
−ジフルオロアニリン２９２ｇを得た。Example 1 Preparation of 2- (3 ', 5'-difluoro-4'-cyanophenyl) -5-pentylpyrimidine Step 1) 231 g of 2,6-difluoroaniline was dissolved in 400 m of chloroform, and 300 g of bromine was added thereto. Dropped. After refluxing for 1 hour, the reaction solution was poured into a 10% potassium hydroxide solution. It was extracted with chloroform, and the organic layer was washed with 10% potassium hydroxide solution and water. After distilling off chloroform, vacuum distillation was carried out (bp 70-80 ° C /
4mmHg) Recrystallized from hexane to give 4-bromo-2,6
-292 g of difluoroaniline were obtained.
工程２）４−ブロモ−２，６−ジフルオロアニリン１３
２ｇ、シアン化第一銅７０ｇ、Ｎ−メチルピロリドン４
４４ｍをフラスコに取り、３時間還流した。その後、
塩化第二鉄２６６ｇ、濃塩酸８５ｍ、水３１５ｍの
溶液中へ反応液を注いだ。その溶液をクロロホルムで抽
出し、水と１０％水酸化カリウム溶液で洗浄した後、ク
ロロホルムを留去した。残渣を減圧蒸留し（ｂｐ９０〜
１１０℃／４mmHg）ヘキサン、クロロホルムの混合溶媒
中より再結晶し、４−シアノ−２，６ジフルオロアニリ
ン５６ｇを得た。Step 2) 4-Bromo-2,6-difluoroaniline 13
2 g, cuprous cyanide 70 g, N-methylpyrrolidone 4
44 m was placed in a flask and refluxed for 3 hours. afterwards,
The reaction solution was poured into a solution of 266 g of ferric chloride, 85 m of concentrated hydrochloric acid, and 315 m of water. The solution was extracted with chloroform, washed with water and a 10% potassium hydroxide solution, and then chloroform was distilled off. The residue is distilled under reduced pressure (bp90-
It was recrystallized from a mixed solvent of 110 ° C./4 mmHg) hexane and chloroform to obtain 56 g of 4-cyano-2,6 difluoroaniline.
工程３）亜硝酸ナトリウム２４ｇを濃硫酸１８０ｍ中
へ加え、１０℃以下に冷却後酢酸３８ｍを加えた。そ
の後溶液が２０〜２５℃に保つように４−シアノ−２，
６ジフルオロアニリン５３ｇを徐々に加えた。１時間２
０〜２５℃で攪拌後４８％臭化水素酸溶液１８０ｍ中
へ臭化第一銅６０ｇを溶解してその中へ反応液を滴下し
た。滴下終了後室温で１５時間攪拌した。反応液に水を
加えた後、クロロホルムで抽出し、水洗を行なった。有
機層のクロロホルムを留去し、残渣をメタノール、アセ
トン混合溶媒中から再結晶し、２−ブロモ−５−シアノ
−１，３−ジフルオロベンゼン２５ｇを得た。Step 3) 24 g of sodium nitrite was added into 180 m of concentrated sulfuric acid, and after cooling to 10 ° C or lower, 38 m of acetic acid was added. Then 4-cyano-2, so as to keep the solution at 20 to 25 ° C,
53 g of 6-difluoroaniline were gradually added. 1 hour 2
After stirring at 0 to 25 ° C, 60 g of cuprous bromide was dissolved in 180 m of 48% hydrobromic acid solution, and the reaction solution was added dropwise thereto. After completion of dropping, the mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, followed by extraction with chloroform and washing with water. Chloroform of the organic layer was distilled off, and the residue was recrystallized from a mixed solvent of methanol and acetone to obtain 25 g of 2-bromo-5-cyano-1,3-difluorobenzene.
工程４）２−ブロモ−５−シアノ−１，３−ジフルオロ
ベンゼン２５ｇをエタノール４８ｍ、ベンゼン１６５
ｍの混合溶媒中へ溶し、０℃以下に冷却後乾燥塩化水
素ガスを１時間吸収させた。その後反応液の溶媒を留去
し、残渣の結晶エーテルで洗浄した。得られた結晶をエ
タノール４８ｍ中へ加え攪拌し、０℃以下に冷却し
た。この中へ１６％アンモニア吸収エタノールを加えた
後１時間攪拌した。反応液の溶媒を留去し、残渣の結晶
をエーテルで洗浄し、４−ブロモ−３，５−ジフルオロ
ベンズアミジン塩酸塩２７ｇを得た。Step 4) 25 g of 2-bromo-5-cyano-1,3-difluorobenzene was added to 48 m of ethanol and benzene 165.
It was dissolved in a mixed solvent of m and cooled to 0 ° C. or lower, and dry hydrogen chloride gas was absorbed for 1 hour. Then, the solvent of the reaction solution was distilled off, and the residue was washed with crystalline ether. The obtained crystals were added to 48 m of ethanol, stirred, and cooled to 0 ° C or lower. 16% Ammonia-absorbed ethanol was added thereto, and the mixture was stirred for 1 hour. The solvent of the reaction solution was distilled off, and the crystals of the residue were washed with ether to obtain 27 g of 4-bromo-3,5-difluorobenzamidine hydrochloride.
工程５）エタノール２２０ｍ中へ金属ナトリウム２．
８ｇを溶かし、ナトリウムエチラート溶液を調整する。
その中へ４−ブロモ−３，５−ジフルオロベンズアミジ
ン塩酸塩４ｇ、３−エトキシ−２−ペンチルアクロレイ
ン（合成方法はChem.Ber.104,665-667(1971)参照）４．
７ｇを加えるその後室温で一晩攪拌後、１時間還流し
た。その反応液のエタノールを留去後、クロロホルムを
加え水洗を行ない、クロロホルムを留去した。残渣を減
圧蒸留し（ｂｐ１４０〜１５０℃／２mmHg）その後シリ
カゲル−クロロホルムカラムクロマトグラフィーで精製
し、２−（３′，５′−ジフルオロ−４′−ブロモフエ
ニル）−５−ペンチルピリミジン０．７ｇを得た。Step 5) Metallic sodium into 220 m of ethanol 2.
Dissolve 8 g and adjust the sodium ethylate solution.
4-Bromo-3,5-difluorobenzamidine hydrochloride (4 g), 3-ethoxy-2-pentylacrolein (see Chem. Ber. 104, 665-667 (1971) for synthetic method) 4.
After adding 7 g, the mixture was stirred at room temperature overnight and then refluxed for 1 hour. After ethanol of the reaction solution was distilled off, chloroform was added and the mixture was washed with water to remove chloroform. The residue was distilled under reduced pressure (bp 140-150 ° C / 2 mmHg) and then purified by silica gel-chloroform column chromatography to obtain 0.7 g of 2- (3 ', 5'-difluoro-4'-bromophenyl) -5-pentylpyrimidine. It was
（工程６）２−（３′，５′−ジフルオロ−４′−ブロ
モフエニル）−５−ペンチルピリミジン０．７ｇ。ソア
ン化第一銅０．５ｇ、Ｎ−メチルピロリドン３．５ｍ
をフラスコに取り、５時間還流した。その後、塩化第二
鉄１．７ｇ、濃塩酸０．４ｍ、水１．７ｍの溶液中
へ反応液を注いだ。その溶液をクロロホルムで抽出し、
水と１０％水酸化カリウム溶液で洗浄した後クロロホル
ムを留去した。残渣をシリカゲル−クロロホルムのカラ
ムクロマトグラフィーで精製後、メタノール中から再結
晶を行ない、２−（３′，５′−ジフルオロ−４′−シ
アノフェニル）−５−ペンチルピリミジン０．２５ｇを
得た。この化合物の結晶−等方性液体転移点（以下Ｃ−
Ｎ点という）は６５．３℃であった。(Step 6) 0.7 g of 2- (3 ', 5'-difluoro-4'-bromophenyl) -5-pentylpyrimidine. Cuprous soanide 0.5 g, N-methylpyrrolidone 3.5 m
Was placed in a flask and refluxed for 5 hours. Then, the reaction solution was poured into a solution of ferric chloride 1.7 g, concentrated hydrochloric acid 0.4 m, and water 1.7 m. The solution was extracted with chloroform,
After washing with water and a 10% potassium hydroxide solution, chloroform was distilled off. The residue was purified by silica gel-chloroform column chromatography and recrystallized from methanol to obtain 0.25 g of 2- (3 ', 5'-difluoro-4'-cyanophenyl) -5-pentylpyrimidine. Crystal-isotropic liquid transition point (hereinafter C-
The N point) was 65.3 ° C.
実施例２ 実施例１と同様にして２−（３′，５′−ジフルオロ−
４′−シアノフェニル）−５−ブチルピリミジンを合成
した。この化合物のＣ−Ｉ点は７９．３℃であった。Example 2 In the same manner as in Example 1, 2- (3 ', 5'-difluoro-
4'-Cyanophenyl) -5-butylpyrimidine was synthesized. The C-I point of this compound was 79.3 degreeC.
応用例１ 市販の混合液晶ＺＬＩ−１５６５（メルク社製品、Ｎ−
Ｉ点８９．３℃）をベース液晶とし、現在一般的にＶ
ｔｈを低くする目的で使用されている２−（４′−シア
ノフェニル）−５−ペンチルピリミジンと本発明化合物
である実施例１の２−（３′，５′−ジフルオロ−４′
−シアノフェニル）−５−ペンチルピリミジンの特性比
較を行なった。Application Example 1 Commercially available mixed liquid crystal ZLI-1565 (product of Merck & Co., N-
The point I is 89.3 ° C) is used as the base liquid crystal, and is currently generally V
2- (4'-cyanophenyl) -5-pentylpyrimidine used for the purpose of lowering th and 2- (3 ', 5'-difluoro-4' of Example 1 which is the compound of the present invention.
The characteristics of -cyanophenyl) -5-pentylpyrimidine were compared.
〔組成物Ｂ〕 よりなる組成物Ａ及びＢを作り、それぞれ厚さ７μｍの
ＴＮセルに封入し、交流スタテック駆動、２０℃で電圧
−輝度特性を測定した。結果を表１に示す。 [Composition B] Compositions A and B consisting of the above were prepared, and each was enclosed in a TN cell having a thickness of 7 μm, and the voltage-luminance characteristics were measured at 20 ° C. under AC static drive. The results are shown in Table 1.
尚表中Ｖ10は透過率１０％時の電圧値であり、ＴＮセル
測定方向θ＝９０°からの測定値である。またα及びβ
はそれぞれ視角特性及びしきい特性を表わす因子であ
り、それぞれ次のように定義した。 In the table, V 10 is a voltage value when the transmittance is 10% and is a measured value from the TN cell measuring direction θ = 90 °. And α and β
Are factors representing the viewing angle characteristic and the threshold characteristic, respectively, and are defined as follows.
α＝θ９０°Ｖ50／θ５０°Ｖ50 β＝θ９０°Ｖ10／θ９０°Ｖ90 ［発明の効果］ 以上に述べた如く、本発明の化合物は一般的な液晶組成
物に混合することにより、電気光学特性（α値・β値）
を悪くすることなくしきい値電圧を大幅に下げる効果が
ある。 α = θ90 ° V 50 / θ50 ° V 50 β = θ90 ° V 10 / θ90 as discussed ° V 90 [Effect of the Invention] above, by mixing the compounds general liquid crystal composition of the present invention, Electro-optical characteristics (α value / β value)
It has the effect of significantly reducing the threshold voltage without deteriorating the threshold voltage.
これらの点で本発明は、現在液晶表示装置の主流となっ
ているスーパーツイステッドネマチック型表示の液晶組
成物の基本的成分として極めて有用である。From these points, the present invention is extremely useful as a basic component of a liquid crystal composition of super twisted nematic type display, which is currently the mainstream of liquid crystal display devices.
Claims (1)
を示す） で表わされるピリミジン誘導体。1. A general formula (In the above formula, R represents a linear alkyl group having 1 to 10 carbon atoms).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1173511A JPH0629262B2 (en) | 1989-07-05 | 1989-07-05 | Pyrimidine derivative |
| DE69004844T DE69004844T2 (en) | 1989-03-30 | 1990-02-26 | Pyrimidine derivatives. |
| EP90301999A EP0390329B1 (en) | 1989-03-30 | 1990-02-26 | Pyrimidine derivative |
| US07/498,198 US5030382A (en) | 1989-03-30 | 1990-03-23 | Pyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1173511A JPH0629262B2 (en) | 1989-07-05 | 1989-07-05 | Pyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0338572A JPH0338572A (en) | 1991-02-19 |
| JPH0629262B2 true JPH0629262B2 (en) | 1994-04-20 |
Family
ID=15961883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1173511A Expired - Lifetime JPH0629262B2 (en) | 1989-03-30 | 1989-07-05 | Pyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0629262B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4505879B2 (en) * | 1999-06-01 | 2010-07-21 | Ｄｉｃ株式会社 | Liquid crystal composition and liquid crystal display element |
| JP4505880B2 (en) * | 1999-06-01 | 2010-07-21 | Ｄｉｃ株式会社 | Liquid crystal composition and liquid crystal display element |
| CN1248033C (en) * | 2000-02-28 | 2006-03-29 | 默克专利股份有限公司 | Supertwisted nematic liquid crystal displays, liquid crystal compositions and compounds |
| JP4872147B2 (en) | 2000-07-25 | 2012-02-08 | Ｄｉｃ株式会社 | Liquid crystal composition and liquid crystal display element |
-
1989
- 1989-07-05 JP JP1173511A patent/JPH0629262B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0338572A (en) | 1991-02-19 |
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