JPS6033420B2 - liquid crystal compound - Google Patents
liquid crystal compoundInfo
- Publication number
- JPS6033420B2 JPS6033420B2 JP16012379A JP16012379A JPS6033420B2 JP S6033420 B2 JPS6033420 B2 JP S6033420B2 JP 16012379 A JP16012379 A JP 16012379A JP 16012379 A JP16012379 A JP 16012379A JP S6033420 B2 JPS6033420 B2 JP S6033420B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal compound
- acid
- tetrahydronaphthyl
- 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.)
- Expired
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- -1 ester compound Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】
本発明は、ネマチック層を呈する新規な液晶性化合物に
関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel liquid crystalline compound exhibiting a nematic layer.
ある有機化合物は、結晶性の固体と無秩序に配列してい
る液相との間の中間相である液晶相を形成する。Some organic compounds form a liquid crystal phase, which is an intermediate phase between a crystalline solid and a disordered liquid phase.
当該液晶相内に於いて、分子は広範囲な規則正しい配列
をとり、その配列の仕方によって液晶層を次の三種に分
類することができる。‘１１スメクチツク層‘２）ネマ
チック層
｛３１ コレステリツク層
スメクチツク層は広範囲な規則配列が実質的に薄層であ
るタイプであり、ネマチック層は分子の配列が実質的に
縁状則ち分子が分子の長軸方向に平行に配列するタイプ
である。Within the liquid crystal phase, molecules are arranged in a wide range of regular arrangements, and the liquid crystal layer can be classified into the following three types depending on the way the molecules are arranged. '11 Smectic Layer' 2) Nematic Layer {31 Cholesteric Layer A smectic layer is a type in which a wide range of ordered arrangements are substantially thin layers. This type is arranged parallel to the long axis direction.
コレステリツク層はネマチツク層のサブクラスとして含
まれる場合もあるように、ネマチツク層とよく類似して
おり、ネマチツク中間層の線状配列に加えて、らせん状
の４・範囲の規則正しい配列を有するタイプである。近
年、特にネマチツク層を呈する液晶は表示体素子として
利用され、腕時計、電卓などの表示部に使用されている
のは周知のとおりである。The cholesteric layer is often included as a subclass of the nematic layer, and is very similar to the nematic layer.In addition to the linear arrangement of the nematic intermediate layer, the cholesteric layer has a regular arrangement of four spiral regions. . In recent years, liquid crystals exhibiting a nematic layer in particular have been utilized as display elements, and it is well known that they are used in the display parts of wristwatches, calculators, and the like.
このように液晶を表示材料として用いる場合、幾種類か
の液晶物質を混合して液晶組成物として用いる場合がほ
とんどである。一般に知られているように、該液晶組成
物の使用液晶温度範囲、応答性などは、調合する液晶物
質を経験的に、適当に選択することにより改善できる。
本発明は、上記のような液晶組成物の一材料として使用
されるネマチツク液晶化合物を提供することを目的とし
た。When liquid crystal is used as a display material in this way, in most cases several types of liquid crystal substances are mixed and used as a liquid crystal composition. As is generally known, the usable liquid crystal temperature range, responsiveness, etc. of the liquid crystal composition can be improved by appropriately selecting the liquid crystal material to be prepared empirically.
An object of the present invention is to provide a nematic liquid crystal compound that can be used as a material for the above-mentioned liquid crystal composition.
本発明の化合物は、一般式 （但し、Ｒは炭素数１〜８の直鏡アルキル基を示す。The compounds of the present invention have the general formula (However, R represents a straight mirror alkyl group having 1 to 8 carbon atoms.
）で表わされ、２−クロロー４一（トランス−４−ｎー
アルキルシクロヘキシルカルボニルオキシ）安息香酸２
−（５・６・７・８ーテトラヒドロナフチル）ェステル
類である。以下実施例に従い、本発明によって提供され
る化合物の製造方法を詳細に説明する。), 2-chloro4-(trans-4-n-alkylcyclohexylcarbonyloxy)benzoic acid 2
-(5,6,7,8-tetrahydronaphthyl) esters. The method for producing the compound provided by the present invention will be described in detail below with reference to Examples.
実施例 １ 下記の反応式に従って合成した。Example 1 It was synthesized according to the reaction formula below.
（式中、Ｒは炭素数１〜８の直鎖アルキル基を示す。(In the formula, R represents a straight chain alkyl group having 1 to 8 carbon atoms.
）Ｓｔｅｐｌ：２−クロロー４ーヒドロキシ安息香酸１
１．７夕をトルェン６００肌に溶解し、この溶液に５・
６・７・８−テトラヒドロー２ーナフトール１０夕、硫
酸０．２叫、棚酸０．２夕をそれぞれ加え、３０時間還
流した。続いて、トルェンを留去し、残留物である粗２
′ークロロ−４ーヒドロキシ安息香酸２一（５・６・７
・８ーテトラヒドロナフチル）ヱステルをアセトニトリ
ルで再結晶し、次に、メタノールで再結晶した。ｍｐ１
３８〜１４０００
該化合物の赤外線吸光図を第１図に示した。) Stepl: 2-chloro-4-hydroxybenzoic acid 1
Dissolve 1.7 liters in toluene 600 skin, and add 5 liters to this solution.
6,7,8-tetrahydro-2-naphthol (10 times), sulfuric acid (0.2 times) and shelf acid (0.2 times) were added thereto, and the mixture was refluxed for 30 hours. Subsequently, toluene was distilled off, and the residue, crude 2
'-Chloro-4-hydroxybenzoic acid 2-(5, 6, 7
- 8-tetrahydronaphthyl) ester was recrystallized from acetonitrile and then from methanol. mp1
38-14000 The infrared absorption diagram of this compound is shown in FIG.
ｓｔｅｐ２：市販のトランス一４−ｎーベンチルシクロ
ヘキシルカルボン酸及び塩化チオニルの反応から常法に
より、トランス−４一ｎ−ベンチルシクロヘキシルカル
ボン酸クロラィドを合成した。ｂｐ８５〜聡℃／０．５
側Ｈｇｓにｐ３：ｓｔｅｐｌで得た、２−クロロー４ー
ヒドロキシ安息香酸２−（５・６・７・８−テトラヒド
ロナフチル）ェステル１．３６夕をピリジン２０叫に溶
解し、これに、ｓｔｅｐ２で得たトランス−４−ｎ−ベ
ンチルシクロヘキシルカルボン酸クロラィド０．９７夕
を加え、室温で放置した。Step 2: Trans-41-n-bentylcyclohexylcarboxylic acid chloride was synthesized by a conventional method from the reaction of commercially available trans-4-n-bentylcyclohexylcarboxylic acid and thionyl chloride. bp85~Satoshi℃/0.5
On the side Hgs, 1.36 g of 2-chloro-4-hydroxybenzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester obtained in step 1 was dissolved in 20 g of pyridine, and added to this. 0.97 g of trans-4-n-bentylcyclohexylcarboxylic acid chloride was added thereto, and the mixture was allowed to stand at room temperature.
１曲時間後、反応混合物を冷濃塩酸中に注ぎ込み、析出
した結晶を炉別した後、その結晶をへキサンで再結晶し
た。After one hour, the reaction mixture was poured into cold concentrated hydrochloric acid, and the precipitated crystals were separated in a furnace and then recrystallized from hexane.
ｍｐ ６２．５ｑ○ ｃｐ ９１００該化合物の赤外線
吸光図を第２図に示した。mp 62.5q○ cp 9100 The infrared absorption diagram of the compound is shown in FIG.
このようにして、係わる２ークロロー４一（トランス−
４−ｎーベンチルシクロヘキシルカルボニルオキシ）安
息香酸 ２−（５・６・７・８−テトラヒドロナフチル
）ェステルを得た。実施例 ２、３
実施例１と同様にして、前記２ークロロー４ーヒドロキ
シ安息香酸 ２−（５・６・７・８−テトラヒドロナフ
チル）ェステルと、第１表に示す、Ｎｏ．２、３の酸ク
ロラィドを合成し、ェステル化を行ない表２に示すＮｏ
．Ｚ、３′の液晶化化合物を合成した。In this way, the involved 2-kuro-4-1 (trans-
4-n-bentylcyclohexylcarbonyloxy)benzoic acid 2-(5,6,7,8-tetrahydronaphthyl)ester was obtained. Examples 2 and 3 In the same manner as in Example 1, the 2-chloro-4-hydroxybenzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester and No. 2 shown in Table 1 were prepared. Acid chlorides 2 and 3 were synthesized and esterified to obtain No. 2 shown in Table 2.
．． A liquid crystal compound of Z and 3' was synthesized.
表 １
表 ２
尚、本発明に係わる表２のＮｏ．２′、３′の液晶性化
合物の赤外線吸光図を第３，４図に示す。Table 1 Table 2 Note that No. 2 in Table 2 related to the present invention. The infrared absorption diagrams of the liquid crystalline compounds 2' and 3' are shown in Figures 3 and 4.
本発明によって提供させるェステル化合物は、表−２に
示す温度範囲のネマチック液晶相を呈する。これらは、
Ａｐｐｌｉｅｄ、Ｐｈｙｓｉｃｓ、Ｌｅｔにｒ、Ｖｏ１
２ふＮｏ．４、１５、Ａｕｇ瓜ｔｌ９７４などに報告さ
れている二周波駆動液晶表示体の液晶材料として、また
、既存の液晶性化合物と混合し、種々の液晶表示体に用
いられる液晶組成物の一材料として使用できる。The ester compound provided by the present invention exhibits a nematic liquid crystal phase in the temperature range shown in Table 2. these are,
Applied, Physics, Let r, Vol1
2F No. 4, 15, as a liquid crystal material for dual-frequency drive liquid crystal display bodies reported in Aug. Can be used.
第１図〜第４図は、それぞれ、下記の化合物の赤外線吸
光図を示す。
第１図・・…・２−クロロ−４ーヒドロキシ安息香酸２
−（５・６・７・８−テトラヒドロナフチル）ェステル
、第２図……２ークロロー４−（トランス一４−ｎ−ベ
ンチルシクロヘキシルカルボニルオキシ）安息香酸 ２
−（５・６・７・８−テトラヒドロナフチル）ェステル
、第３図……２ークロロ−４一（トランス一４一ｎ−プ
ロピルシクロヘキシルカルボニルオキシ）安息香酸 ２
一（５・６・７・８一テトラヒドロナフチル）ヱステル
、第４図……２−クロロ−４−（トランス−４一ｎープ
チルシクロヘキシルカルボニルオキシ）安息香酸 ２一
（５・６・７・８−テトラヒドロナフチル）エステル。
第１図第２図
図
の
鉄
図
寸
船Figures 1 to 4 show infrared absorption diagrams of the following compounds, respectively. Figure 1...2-chloro-4-hydroxybenzoic acid 2
-(5,6,7,8-tetrahydronaphthyl) ester, Figure 2... 2-chloro4-(trans-4-n-bentylcyclohexylcarbonyloxy)benzoic acid 2
-(5,6,7,8-tetrahydronaphthyl) ester, Figure 3...2-chloro-4-(trans-41-n-propylcyclohexylcarbonyloxy)benzoic acid 2
-(5,6,7,8-tetrahydronaphthyl)ester, Figure 4...2-chloro-4-(trans-4-n-butylcyclohexylcarbonyloxy)benzoic acid 2-(5,6,7,8 -tetrahydronaphthyl) ester. Figure 1 Figure 2 Iron map size ship
Claims (1)
１〜８の直鎖アルキル基を示す。 ）[Claims] 1. A liquid crystal compound whose general formula is represented by the following formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, R represents a straight chain alkyl group having 1 to 8 carbon atoms.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16012379A JPS6033420B2 (en) | 1979-12-10 | 1979-12-10 | liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16012379A JPS6033420B2 (en) | 1979-12-10 | 1979-12-10 | liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5683447A JPS5683447A (en) | 1981-07-08 |
| JPS6033420B2 true JPS6033420B2 (en) | 1985-08-02 |
Family
ID=15708356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16012379A Expired JPS6033420B2 (en) | 1979-12-10 | 1979-12-10 | liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6033420B2 (en) |
-
1979
- 1979-12-10 JP JP16012379A patent/JPS6033420B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5683447A (en) | 1981-07-08 |
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