JPH0219364A - Ester derivative of alpha-methylallylfluoropyrimidinylphenols and liquid crystal composition thereof - Google Patents
Ester derivative of alpha-methylallylfluoropyrimidinylphenols and liquid crystal composition thereofInfo
- Publication number
- JPH0219364A JPH0219364A JP63167696A JP16769688A JPH0219364A JP H0219364 A JPH0219364 A JP H0219364A JP 63167696 A JP63167696 A JP 63167696A JP 16769688 A JP16769688 A JP 16769688A JP H0219364 A JPH0219364 A JP H0219364A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- crystal composition
- alpha
- ester
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 150000002148 esters Chemical class 0.000 title claims abstract description 15
- 239000000126 substance Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004185 ester group Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 31
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000002585 base Substances 0.000 abstract description 4
- 235000010290 biphenyl Nutrition 0.000 abstract description 4
- 239000004305 biphenyl Substances 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 3
- 230000007704 transition Effects 0.000 abstract description 3
- 239000002262 Schiff base Substances 0.000 abstract description 2
- 150000004753 Schiff bases Chemical class 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 ester compound Chemical class 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JXPGQFKJNKWDKP-KTSLABGISA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C(O)=O)CC1 JXPGQFKJNKWDKP-KTSLABGISA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical class OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- JAIZEOKRVZKODU-UHFFFAOYSA-N 5-pentylpyrimidine Chemical compound CCCCCC1=CN=CN=C1 JAIZEOKRVZKODU-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
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 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
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LITQLZTWAYBHOB-UHFFFAOYSA-N n,n-diethylaniline;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)C1=CC=CC=C1 LITQLZTWAYBHOB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明はα−メチルアリルフルオロピリミジニルフェノ
ール類のエステル誘導体および該化合物を有効成分とし
て含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an ester derivative of α-methylallylfluoropyrimidinylphenols and a liquid crystal composition containing the compound as an active ingredient.
液晶を利用した表示素子は時計、電卓等に広く使用され
ている。。Display elements using liquid crystals are widely used in watches, calculators, etc. .
これらの液晶表示素子は液晶物質の光学異方性および誘
電異カ性を利用したものである。液晶相にはネマチック
液晶相、スメクチック液晶相、コレステリック液晶相が
あり、そのうちネマチック型晶を利用したものが最も広
く実用化されている。These liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials. Liquid crystal phases include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, among which those using nematic type crystals are most widely put into practical use.
それらには液晶表示に応用されている電気光学効果に対
応して、ＴＮ（ねじれネマチック型）、ＤＳ（動的散乱
）型、ゲスト・ホスト型、ＤＡＰ型等の表示素子がある
。それぞれに使用される液品物質は自然界のなるべく広
い温度範囲で液晶相を示すものが望ましい。These display elements include TN (twisted nematic type), DS (dynamic scattering) type, guest-host type, DAP type, etc. corresponding to the electro-optic effect applied to liquid crystal displays. It is desirable that the liquid substances used in each case exhibit a liquid crystal phase over as wide a natural temperature range as possible.
現在のところ、単一の液晶物質で、そのような条件をみ
なす物質はなく数種の液晶物質、または、さらに非液晶
物質を混合して実用に供している。At present, there is no single liquid crystal substance that satisfies such conditions, and several types of liquid crystal substances or even non-liquid crystal substances are mixed and put into practical use.
これらの物質は水分、光、熱、空気等に対しても安定で
あることを要求されている。These substances are required to be stable against moisture, light, heat, air, and the like.
近年、表示素子の多駆動表示が望まれているが、従来の
ＴＮ型方式では表示部位が劣るため、新たに一連のＳＴ
Ｎ （スーパーツイスト）型表示素子がＭ、シャットら
（Ａｐｐｌ、 Ｐｈｙｓ、 Ｌθｕ、、 ５虹、２３６
（１９８７） ｌによって開発され、多駆動表示でも表
示品位が優れたものである。In recent years, multi-drive display of display elements has been desired, but since the display area is inferior in the conventional TN type system, a new series of ST
N (super twist) type display element is M, Shutt et al. (Appl, Phys, Lθu, 5 Rainbow, 236
(1987) and has excellent display quality even in multi-drive displays.
この方式に望まれる液晶化合物の性質は特開昭６３−１
０１４８２号公報に記載されているように、Ｋ３３／に
１１が大きく、Δε／ε□は小さい値が望まれている。The properties of the liquid crystal compound desired for this method are described in JP-A-63-1
As described in Japanese Patent No. 01482, 11 is desired to be large for K33/, and a small value for Δε/ε□ is desired.
ここでＫ は広がり、Ｋ３３は曲げに対する弾性定数を
表わし、Δεは誘電異方性値（液晶分子の長軸方向の誘
電率ε１１と液晶分子の短軸方向の誘電率ε工との差、
ε＋＋−ε工）を表わす。Here, K is the spread, K33 is the elastic constant against bending, and Δε is the dielectric anisotropy value (the difference between the dielectric constant ε11 in the long axis direction of the liquid crystal molecules and the dielectric constant ε11 in the short axis direction of the liquid crystal molecules,
ε＋＋−ε 工).
本発明はＳＴＮ型表不表示素子いて多駆動表示をした場
合にも、適応するに３３／に１１が比較的大きく、相溶
性に優れた化合物であって、他の液晶組成物に配合して
Ｎ−Ｉ点を上昇させることが可能な新規の液晶用化合物
を提供することを目的とする。The present invention is also suitable for multi-drive display in STN type non-display elements, and is a compound having a relatively large ratio of 33/11 to 11, which has excellent compatibility, and which can be blended into other liquid crystal compositions. The object of the present invention is to provide a novel compound for liquid crystals that can increase the N-I point.
更に該化合物を配合した液晶組成物を提供することを目
的とする。A further object of the present invention is to provide a liquid crystal composition containing the compound.
本発明は次の一般式〔Ｉ〕で表わされるα−メチルアリ
ルフルオロピリミジニルフェノール類のエステル誘導体
である。The present invention is an ester derivative of α-methylallylfluoropyrimidinylphenol represented by the following general formula [I].
（但し、（Ｉ）式において、Ｒ１，Ｒ２はそれぞれ直鎖
または枝分れした炭素数１〜１５のアルキル基またはア
ルコキシ基を示し、ｎは１又は２であることを示す、）
本発明はまた該化合物を少なくとも一種類含有する液晶
組成物である。(However, in formula (I), R1 and R2 each represent a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, and n represents 1 or 2.) The present invention It is also a liquid crystal composition containing at least one type of the compound.
本発明のα−メチルアリルフルオロピリミジニルフェノ
ール類のエステル誘導体以外の他の成分で、液晶組成物
の成分にできる化合物としては、例えばエステル系、シ
ップ塩基系、ビフェニル系、フェニルシクロヘキサン系
、複素環系等の液晶化合物を挙げることができる。Examples of compounds other than the ester derivatives of α-methylallylfluoropyrimidinylphenols of the present invention that can be used as components of the liquid crystal composition include ester-based, ship base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based compounds. Liquid crystal compounds such as the following can be mentioned.
本発明のα−メチルアリルフルオロピリミジニルフェノ
ール類のエステル誘導体の製造方法としては、例えば次
式の反応によって製造できる。The ester derivative of α-methylallylfluoropyrimidinylphenol of the present invention can be produced, for example, by the following reaction.
煮沸還流
Ｎ、Ｎ−ジエチルアニリン
ピリジン
（上式中のＲ１，Ｒ２，ｎは前記と同じである。）すな
わちクロチル−ピリミジニルフルオロフェニルエーテル
誘導体をＮ、Ｎ−ジエチルアニリンを溶媒として、煮沸
還流して、２−α−メチルアリル−４−ピリミジニル−
６−フルオロフェノール誘導体を製造した。Boiling and refluxing N,N-diethylaniline pyridine (R1, R2, n in the above formula are the same as above), that is, a crotyl-pyrimidinyl fluorophenyl ether derivative, was boiled and refluxed using N,N-diethylaniline as a solvent. , 2-α-methylallyl-4-pyrimidinyl-
A 6-fluorophenol derivative was produced.
この化合物に目的物に対応するカルボン酸クロリドを加
え、ピリジン存在下に反応を行わしめ、目的とするエス
テル化合物を製造した。A carboxylic acid chloride corresponding to the target compound was added to this compound, and the reaction was carried out in the presence of pyridine to produce the target ester compound.
本発明の化合物は、他の多くの液晶化合物、すなわちエ
ステル系、シップ塩基系、ビフェニル系、フェニルシク
ロヘキサン系、複素環系等の液晶化合物との相溶性がよ
く、本発明の化合物を液晶組成物に少量添加することに
よって、そのＮ−Ｉ点を上昇させることができる。The compound of the present invention has good compatibility with many other liquid crystal compounds, such as ester-based, ship base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds, and the compound of the present invention can be used in liquid crystal compositions. By adding a small amount to , the N-I point can be raised.
その上、本発明の化合物を液晶組成物に加えるとに３３
／に１１の値を大きくすることができる。Moreover, when the compound of the present invention is added to a liquid crystal composition, 33
The value of 11 can be increased to /.
以下に実施例によって、本発明を更に具体的に説明する
が、本発明は、この実施例によって同等限定されるもの
ではない。EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to the same extent by these Examples.
（実施例１）
（１）２−フルオロ−４−（２−（５−ペンチル）ピリ
ミジニル〕−６−α−メチルアリルフ二ノールの製造。(Example 1) (1) Production of 2-fluoro-4-(2-(5-pentyl)pyrimidinyl]-6-α-methylallylphinol.
２−（３−フルオロ−４−ヒドロキシフェニル）５−ペ
ンチルピリミジン９．２ｇ （０，０４モル）と無水炭
酸カリウム８０ｇにアセトン５００ｍ１を加え、よく撹
拌しながら臭化クロチル１３ｆ（０，１モル）を加えた
。そのまま室温で２時間撹拌した後に、マントルヒータ
で加熱し、還流を４８時間行った。Add 500 ml of acetone to 9.2 g (0.04 mol) of 2-(3-fluoro-4-hydroxyphenyl)5-pentylpyrimidine and 80 g of anhydrous potassium carbonate, and add crotyl bromide 13f (0.1 mol) while stirring well. added. After stirring at room temperature for 2 hours, the mixture was heated with a mantle heater and refluxed for 48 hours.
反応終了後、不溶物を炉別し、炉液からアセトンを減圧
留去した。After the reaction was completed, insoluble matter was separated from the furnace, and acetone was distilled off from the furnace liquid under reduced pressure.
残った油状物をトルエンを溶媒として活性アルミナでカ
ラムクロマトグラフィーを行った。トルエンを留去し、
残った油状物をエタノールを溶媒として再結晶を行った
。かくして得たものが２（３−フルオロ−４−クロチル
オキシフェニル）５〜ペンチルピリミジンである。The remaining oil was subjected to column chromatography on activated alumina using toluene as a solvent. Distill toluene,
The remaining oil was recrystallized using ethanol as a solvent. The product thus obtained is 2(3-fluoro-4-crotyloxyphenyl)5-pentylpyrimidine.
このものをＮ、Ｎ−ジエチルアニリン４００１１１に溶
かし、８時間窒素雰囲気下に還流した。放冷後５００ｍ
１の６Ｎ塩酸に反応液を加えた。−晩放置後、析出した
沈澱物を炉別し、少量の水でよく洗い、減圧にてよく乾
燥した。このものが２−フルオロ−４−Ｃ２−（５−ペ
ンチル）ピリミジニル〕−６−α−メチルアリルフェノ
ールの塩酸塩である。このものをそのままつぎの反応に
用いた。This product was dissolved in N,N-diethylaniline 400111 and refluxed under nitrogen atmosphere for 8 hours. 500m after cooling
The reaction solution was added to 6N hydrochloric acid in Step 1. - After standing overnight, the precipitate deposited was filtered out, thoroughly washed with a small amount of water, and thoroughly dried under reduced pressure. This is the hydrochloride of 2-fluoro-4-C2-(5-pentyl)pyrimidinyl]-6-α-methylallylphenol. This product was used as it was in the next reaction.
（２）トランス−４−（トランス−４−プロピルシクロ
ヘキシル）シクロヘキサンカルボン酸の２−フルオロ−
４−（２−＜５−ペンチル）ピリミジニル〕−６−α−
メチルアリルフェノールエステルの製造。(2) 2-fluoro- of trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid
4-(2-<5-pentyl)pyrimidinyl]-6-α-
Production of methylallylphenol ester.
２−フルオロ−４−Ｃ２−（５−ペンチル）ピリミジニ
ル〕−６−α−メチルアリルフェノール２．９ｔｒ （
０，０１モル）をピリジン２０ｍ１に溶かし、激しく撹
拌しながら、この溶液にトランス−４−（）ランス−４
−プロピルシクロヘキシル）シクロヘキサンカルボン酸
の酸クロリド２．６ｇ（０，０１モル）をトルエン１０
０ｍ１に溶かしたものを加えよく撹拌した。2-Fluoro-4-C2-(5-pentyl)pyrimidinyl]-6-α-methylallylphenol 2.9tr (
Trans-4-()trans-4 was dissolved in 20 ml of pyridine and stirred vigorously.
-2.6 g (0.01 mol) of acid chloride of cyclohexanecarboxylic acid (propylcyclohexyl) was added to 10 g of toluene.
Add the solution dissolved in 0 ml and stir well.
一晩放置後、反応物を水１００ｍ１に注加し、トルエン
層を分取して、２Ｎ水酸化ナトリウムで洗い、ついで中
性となるまで水でトルエン層を洗った。After standing overnight, the reaction product was poured into 100 ml of water, the toluene layer was separated and washed with 2N sodium hydroxide, and then the toluene layer was washed with water until neutral.
この後、無水硫酸ナトリウムでトルエン層を乾燥後、ト
ルエンを減圧にして留去した。残った固形物をエタノー
ルを溶媒として再結晶し、目的の化合物を製造した。得
られた化合物のクリスタル−ネマチック転移温度（Ｃ−
Ｎ点）は１３９．５〜１４０．４°Ｃ、ネマチック−等
方性液体転移温度（Ｎ−Ｉ点）は１４１．０℃、収量１
．５ｇ（収率３０％）であった。Thereafter, the toluene layer was dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure. The remaining solid was recrystallized using ethanol as a solvent to produce the desired compound. The crystal-nematic transition temperature (C-
N point) is 139.5 to 140.4°C, nematic-isotropic liquid transition temperature (N-I point) is 141.0°C, yield 1
．． 5 g (yield 30%).
同様にしてトランス−４−（トランス−４−プロピルシ
クロヘキシル）シクロヘキサンカルボン酸の代りに対応
するカルボン酸クロリドを、２α−メチルアリル−４−
（３−ペンチルー２−ピリミジニル）−６−フルオロフ
ェノールの代りに対応する２−α−メチルアリル−４（
３−（置換）−２−ピリミジニル）−６−フルオロフェ
ノールを用いて種々のエステル化合物を製造した。Similarly, trans-4-(trans-4-propylcyclohexyl)cyclohexanecarboxylic acid was replaced with the corresponding carboxylic acid chloride, 2α-methylallyl-4-
(3-pentyl-2-pyrimidinyl)-6-fluorophenol instead of the corresponding 2-α-methylallyl-4(
Various ester compounds were prepared using 3-(substituted)-2-pyrimidinyl)-6-fluorophenol.
例えばトランス−４−ヘゲチルシクロヘキサンカルボン
酸の２−フルオロ〜４− ［２−（５−ペンチル）ピリ
ミジニル〕−６−α−メチルアリルフェノールエステル
のｍ、ｐ、７０．２〜７１．８℃、Ｎ−１点６．３°Ｃ
であった。For example, m, p of 2-fluoro to 4-[2-(5-pentyl)pyrimidinyl]-6-α-methylallylphenol ester of trans-4-hegetylcyclohexanecarboxylic acid, 70.2 to 71.8°C , N-1 point 6.3°C
Met.
〔実施例２〕
本発明の液晶化合物以外の液晶化合物とじてトランス−
４−プロピル−（４′ −シアノフェニル）シクロヘキ
サン ２４重量％トランス−４−ベンチルー
（４′ 〜シアノフェニル）シクロヘキサン
３６重量％トランス−４−ヘプチル−（４′ −シア
ノフェニル）シクロヘキサン ２５重厘％ト
ランス−４−ベンチルー（４′ −シアノフェニル）シ
クロヘキサン １５重量％なる液晶組成物（Ａ
）のＮ−１点は７２８０℃。[Example 2] As a liquid crystal compound other than the liquid crystal compound of the present invention, trans-
4-Propyl-(4'-cyanophenyl)cyclohexane 24% by weight trans-4-benzene(4'-cyanophenyl)cyclohexane
The liquid crystal composition (A
)'s N-1 point is 7280°C.
Δεは＋１１．０．２０℃における粘度は２８ＣＰ ＋
Δｎ（液晶分子長軸方向の屈折率ｎｌ＋と液晶分子短軸
方向の屈折率ｎ上との差：ｎｌｌ ｎ上）はｏ 、
１４０ 、 Ｋ３３／に１１は１，８２である。Δε is +11.0.Viscosity at 20℃ is 28CP +
Δn (difference between the refractive index nl+ in the long axis direction of the liquid crystal molecule and the refractive index n above in the short axis direction of the liquid crystal molecule: nll n above) is o,
140, K33/ni 11 is 1,82.
液晶セルとしては、酸化ケイ素をコーティングし、ラビ
ング処理した酸化スズ透明電極を有する基板を対向させ
て組立てた電極間距離１０μｍのものを用意した。A liquid crystal cell was prepared in which substrates coated with silicon oxide and having transparent tin oxide electrodes subjected to rubbing treatment were assembled to face each other, and the distance between the electrodes was 10 μm.
上記の液晶組成物（Ａ）を封入して２０゛Ｃでその特性
を測定したところ、しきい値電圧は１．８２Ｖであった
。When the above liquid crystal composition (A) was sealed and its characteristics were measured at 20°C, the threshold voltage was 1.82V.
この液晶組成物（Ａ）８５重１％に本発明の実施例１−
（２）で製造したトランス−４−（トランス−４−グ
ロビルシクロヘキシル）シクロヘキサンカルボン酸の２
−フルオロ−４−（２−（５ペンチル）ピリミジニルツ
ー６−α−メチルアリルフェノールエステル１５重量％
を溶解した組成物のＮ−１点は７９．２℃、Δεは１０
．６、Δｎは０．１３５となり、粘度は４１ｃｐである
。Example 1 of the present invention was added to 85% by weight of this liquid crystal composition (A).
2 of trans-4-(trans-4-globylcyclohexyl)cyclohexanecarboxylic acid produced in (2)
-Fluoro-4-(2-(5pentyl)pyrimidinyl-6-α-methylallylphenol ester 15% by weight)
The N-1 point of the composition dissolved is 79.2℃, Δε is 10
．． 6, Δn is 0.135, and the viscosity is 41 cp.
Ｋ３３／に１１は１．９３でＳＴＮ用として好適であっ
た。K33/Ni11 had a value of 1.93, which was suitable for STN.
本発明のα−メチルアリルフルオロピリミジニルフェノ
ール類のエステル誘導体は新規な化合物であり、液晶表
示用に使用して有用な化合物である。The ester derivative of α-methylallylfluoropyrimidinylphenol of the present invention is a novel compound and is a compound useful for use in liquid crystal displays.
また、本発明の化合物は、他の多くの液晶化合物、すな
わちエステル系、シッフ塩基系、ビフェニル系、フェニ
ルシクロヘキサン系、複素環系等の液晶化合物との相溶
性がよく、本発明の化合物を液晶組成物に少量添加する
ことによって、そのＮ−Ｉ点を上昇させることができる
。Furthermore, the compound of the present invention has good compatibility with many other liquid crystal compounds, such as ester-based, Schiff base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds. By adding small amounts to the composition, its N-I point can be raised.
その上、本発明の化合物を液晶組成物に加えるとに３３
／に１１の値を大きくすることができるため、ＳＴＮ型
表示素子用の液晶組成物に好適な化合物である。Moreover, when the compound of the present invention is added to a liquid crystal composition, 33
Since the value of /11 can be increased, it is a compound suitable for liquid crystal compositions for STN type display elements.
Claims (1)
オロピリミジニルフェノール類のエステル誘導体。 ▲数式、化学式、表等があります▼・・・〔 I 〕 （但し、〔 I 〕式において、Ｒ＾１、Ｒ＾２はそれぞ
れ直鎖または枝分れした炭素数１〜１５のアルキル基ま
たはアルコキシ基を示し、ｎは１又は２を示す。） ２、請求項１記載のα−メチルアリルフルオロピリミジ
ニルフェノール類のエステル誘導体を少なくとも一種類
含有する液晶組成物。[Scope of Claims] 1. Ester derivatives of α-methylallylfluoropyrimidinylphenols represented by the general formula [I]. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...[I] (However, in the [I] formula, R^1 and R^2 are each a linear or branched alkyl group having 1 to 15 carbon atoms, or 2. A liquid crystal composition containing at least one ester derivative of α-methylallylfluoropyrimidinylphenol according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63167696A JPH0219364A (en) | 1988-07-07 | 1988-07-07 | Ester derivative of alpha-methylallylfluoropyrimidinylphenols and liquid crystal composition thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63167696A JPH0219364A (en) | 1988-07-07 | 1988-07-07 | Ester derivative of alpha-methylallylfluoropyrimidinylphenols and liquid crystal composition thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0219364A true JPH0219364A (en) | 1990-01-23 |
Family
ID=15854529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63167696A Pending JPH0219364A (en) | 1988-07-07 | 1988-07-07 | Ester derivative of alpha-methylallylfluoropyrimidinylphenols and liquid crystal composition thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0219364A (en) |
-
1988
- 1988-07-07 JP JP63167696A patent/JPH0219364A/en active Pending
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