JPS6043058B2 - liquid crystal compound - Google Patents
liquid crystal compoundInfo
- Publication number
- JPS6043058B2 JPS6043058B2 JP15617179A JP15617179A JPS6043058B2 JP S6043058 B2 JPS6043058 B2 JP S6043058B2 JP 15617179 A JP15617179 A JP 15617179A JP 15617179 A JP15617179 A JP 15617179A JP S6043058 B2 JPS6043058 B2 JP S6043058B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- benzoyloxy
- acid
- crystal compound
- chloro4
- 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
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、ネマチック液晶相を呈する新規エステル化合
物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel ester compounds exhibiting a nematic liquid crystal phase.
液晶相は、ある有機化合物によつて示され、該液晶相内
に於ける分子の配列状態により、次のタイプに分類され
ている。The liquid crystal phase is represented by a certain organic compound, and is classified into the following types depending on the arrangement of molecules within the liquid crystal phase.
１ スメクチック液晶
２ ネマチック液晶
３ コレステリック液晶
近年、液晶表示体を用いた、時計、電卓などがつＯ 市
場を賑わしているが、これらの液晶表示体には、ネマチ
ック液晶の有する電気光学効果が応用されているのは周
知のとうりである。1. Smectic liquid crystal 2. Nematic liquid crystal 3. Cholesteric liquid crystal In recent years, watches, calculators, etc. that use liquid crystal displays have become popular in the market, but these liquid crystal displays do not utilize the electro-optic effect of nematic liquid crystals. It is well known that
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。In this manner, when liquid crystal is used as a display material, several types of liquid crystal substances are mixed and used as a liquid crystal composition.
該液晶組成物の使用液晶温度範囲、応答性などは、先行
技術において調合する液晶物質を適当に選択することに
より改善が成されることが知られている。本発明は、上
記したような液晶組成物の一材料として使用されるネマ
チック液晶化合物を提供すヨるものである。It is known in the prior art that 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 formulated. The present invention provides a nematic liquid crystal compound used as a material for the liquid crystal composition as described above.
即ち、本発明の化合物は、一般式
（式中、Ｒは５、６または８個の炭素原子を有する直鎖
アルキル基もしくは６個の炭素原子を有する直鎖アルコ
キシ基を示す。That is, the compounds of the present invention have the general formula (wherein R represents a straight-chain alkyl group having 5, 6 or 8 carbon atoms or a straight-chain alkoxy group having 6 carbon atoms.
）で表わされる、５−（２−クロロー４−（ｐ−ｎ−ア
ルキルベンゾイルオキシ）ベンゾイルキシ）インダン及
び５−（２−クロロー４−（ｐ−ｎ−アルコキシベンゾ
イルオキシ）ベンゾイルオキシ）インダン類であり、下
記の方法に従つて合成できる。ＳｔｅＰｌ：市販の、２
−クロロー４−ヒドロキシ安息香酸と、市販の５−ヒド
ロキシインダンを、トルエン中、触媒として、硫酸、硼
酸の存在下でエステル化を行ない、５−（２−クロロー
４−ヒドロキシベンゾイロキシ）インダンを得る。), 5-(2-chloro-4-(p-n-alkylbenzoyloxy)benzoyloxy)indan and 5-(2-chloro-4-(p-n-alkoxybenzoyloxy)benzoyloxy)indan, It can be synthesized according to the method below. StePl: Commercially available, 2
- Esterification of chloro-4-hydroxybenzoic acid and commercially available 5-hydroxyindan in toluene in the presence of sulfuric acid and boric acid as a catalyst yields 5-(2-chloro-4-hydroxybenzoyloxy)indan. obtain.
ＳｔｅＰ２：市販の、ｐ−ｎ−アルキル安息香酸または
、ｐ−ｎ−アルコキシ安息香酸を塩化チオニルと反応せ
しめ、ｐ−ｎ−アルキル安息香酸クロライド、またはｐ
−ｎ−アルコキシ安息香酸クロライドを得る。ＳｔｅＰ
３：ＳｔｅＰｌと、ＳｔｅＰ２で得た両者の化合物をエ
ステル化し、係わる、５−（２−クロロー４−（ｐ−ｎ
−アルキルベンゾイルオキシ）ベンゾイルオキシ）イン
ダン、及び５−（２−クロロー４−（ｐ−ｎ−アルコキ
シベンゾイルオキシ）ベンゾイルオキシ）インダンを得
る。SteP2: Commercially available p-n-alkylbenzoic acid or p-n-alkoxybenzoic acid is reacted with thionyl chloride to produce p-n-alkylbenzoic acid chloride or p-n-alkylbenzoic acid chloride.
-n-alkoxybenzoic acid chloride is obtained. SteP
3: StePl and both compounds obtained in SteP2 are esterified to produce the related 5-(2-chloro4-(p-n
-alkylbenzoyloxy)benzoyloxy)indan and 5-(2-chloro4-(p-n-alkoxybenzoyloxy)benzoyloxy)indane are obtained.
以下、実施例に従い、本発明によつて提供される化合物
の製造方法を更に詳しく説明する。Hereinafter, the method for producing the compound provided by the present invention will be explained in more detail with reference to Examples.
実施例１ｓｔｅＰ１：２−クロロー４−ヒドロキシ安息
香酸１６．４ｇをトルエン８００ｍ１に溶解し、この溶
液に５−ヒドロキシインダン１３．４ｆ，硫酸０．３ｍ
１，硼酸０．３ｆをそれぞれ加え、３時間還流下に加熱
した。Example 1 steP1: 16.4 g of 2-chloro-4-hydroxybenzoic acid was dissolved in 800 ml of toluene, and 13.4 f of 5-hydroxyindan and 0.3 ml of sulfuric acid were added to this solution.
1 and 0.3 f of boric acid were added, and the mixture was heated under reflux for 3 hours.
反応後、トルエンを留去し、残渣を、アセトニトリル、
及び、メタノールにより再結晶を行ない、５−（２−ク
ロロー４−ヒドロキシベンゾイルオキシ）インダンを得
た。該化合物の赤外線吸光図を第１図に示す。Ｓｔｅｐ
２：ｐ−ｎ−ペンチル安息香酸１８．５ｙと塩化チオニ
ル３０Ｔｎ１をガスの発生が止むまで還流下に加熱した
。After the reaction, toluene was distilled off, and the residue was dissolved in acetonitrile,
Then, recrystallization was performed using methanol to obtain 5-(2-chloro-4-hydroxybenzoyloxy)indane. The infrared absorption diagram of the compound is shown in FIG. Step
2: 18.5y of p-n-pentylbenzoic acid and 30Tn1 of thionyl chloride were heated under reflux until gas evolution ceased.
還流後、過剰の塩化チオニルを留去し、減圧蒸留により
、ｐ−ｎ−ペンチル安息香酸クロライドを製取した。Ｂ
ｐ８９〜９４取Ｃ／１．０Ｔｒ＄ＴＨｇＳｔｅｐ３：Ｓ
ｔｅｐｌで得た５−（２−クロロー４ーヒドロキシベン
ゾイルオキシ）インダン５ｙをピリジン２５ｍＬに溶解
した、ＳｔｅＰ２で得たｐ−ｎ−ペンチル安息香酸クロ
ライド３ｙを加え、よく混合した後、１ｅ＠間室温に放
置した。After refluxing, excess thionyl chloride was distilled off, and pn-pentylbenzoic acid chloride was produced by distillation under reduced pressure. B
p89-94 C/1.0Tr$THgStep3:S
5-(2-chloro-4-hydroxybenzoyloxy)indane 5y obtained by tepl was dissolved in 25 mL of pyridine, and p-n-pentylbenzoic acid chloride 3y obtained by SteP2 was added thereto, mixed well, and then heated to room temperature for 1e@ I left it there.
放置後、この混合液を、氷片を浮べた冷濃塩酸中に注ぎ
込み、分離析出した結晶を集め、ヘキサンにより再結晶
製取した。Ｃ−１点８８晶Ｃ，Ｉ−Ｎ８ｌ．５よＣ
該化合物の赤外線吸光図を第２図に示す。After standing, this mixed solution was poured into cold concentrated hydrochloric acid with ice chips floating thereon, and the separated and precipitated crystals were collected and recrystallized from hexane. C-1 point 88 crystal C, I-N8l. 5yoC The infrared absorption diagram of the compound is shown in FIG.
こうして、係わる５−（２−クロロー４−（ｐ−ｎ−ペ
ンチルベンゾイルオキシ）ベンゾイルオキシ）インダン
を得た。In this way, the concerned 5-(2-chloro4-(p-n-pentylbenzoyloxy)benzoyloxy)indane was obtained.
又、実施例１と同様にして、前記５−（２−クロロー４
−ヒドロキシベンゾイルオキシ）インダンと、表１に示
す。In addition, in the same manner as in Example 1, the 5-(2-chloro4
-hydroxybenzoyloxy)indan, as shown in Table 1.
ＮＯ．２〜４の酸クロライドを製造し、表−２に示す、
ＮＯ．２″〜４″の液晶性化合物を製造した。（表中、
Ｃは結晶、Ｉは透方性液体、Ｎはネマチック液晶を示し
、それぞれの状態から状態へ転移する温度を示す。No. 2 to 4 acid chlorides were produced and shown in Table 2.
No. A liquid crystalline compound having a size of 2" to 4" was produced. (In the table,
C represents a crystal, I represents a transparent liquid, and N represents a nematic liquid crystal, and represents the temperature at which each state transitions from state to state.
）尚、表２のＮＯ．２″〜５″の化合物の赤外線吸光図
を第３〜５図に示す。) In addition, NO. in Table 2. The infrared absorption diagrams of compounds with sizes 2'' to 5'' are shown in Figures 3 to 5.
本発明によつて提供されるエステル化合物は、表−２に
示す如く、ネマチック液晶相を呈する。The ester compound provided by the present invention exhibits a nematic liquid crystal phase as shown in Table 2.
これらの液晶性化合物は、ｌアプライド・フィジックス
レターズ（ＡｐｐｌｌｅｄＰｈｙｓｉｃｓレＴｔｅｒ
ｓ）■ｏ１、２５ｓ陥．４、１９７拝８月１５日』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、又、既存の液晶性化合物と混合して、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
。These liquid crystalline compounds are described in Applied Physics Letters.
s)■o1, 25s failure. 4, August 15, 197'' and other liquid crystal compositions used as liquid crystal materials for dual-frequency drive liquid crystal displays, and mixed with existing liquid crystal compounds for various liquid crystal displays. Can be used as one material.
第１図〜第５図は、下記の化合物のそれぞれ赤外線吸光
図を示す。
第１図・・・・・・５−（２−クロロー４−ヒドロキシ
ベンゾイルオキシ）インダン、第２図・・・・・・５−
（２ークロロー４−（ｐ−ｎ−ペンチルベンゾイルオキ
シ）ベンゾイルオキシ）インダン、第３図・・・・５−
（２−クロロー４−（ｐ−ｎ−ヘキシルベンゾイルオキ
シ）ベンゾイルオキシ）インダン、第４図・・・・・・
５−（２−クロロー４−（ｐ−ｎ−オクチルベンゾイル
オキシ）ベンゾイルオキシ）インダン、第５図・・・・
・・５−（２−クロロー４−（ｐ一ｎ−ヘキシルオキシ
さンゾイルオキシ）ベンゾイルオキシ）インダン。Figures 1 to 5 show infrared absorption diagrams of the following compounds, respectively. Figure 1...5-(2-chloro4-hydroxybenzoyloxy)indane, Figure 2...5-
(2-chloro4-(p-n-pentylbenzoyloxy)benzoyloxy)indane, Figure 3...5-
(2-chloro4-(p-n-hexylbenzoyloxy)benzoyloxy)indane, Figure 4...
5-(2-chloro4-(p-n-octylbenzoyloxy)benzoyloxy)indane, Figure 5...
...5-(2-chloro4-(p-n-hexyloxy-benzoyloxy)benzoyloxy)indan.
Claims (1)
アルキル基もしくは６個の炭素原子を有する直鎖アルコ
キシ基を示す。 ）で表わされることを特徴とする液晶性化合物。[Claims] 1. The general formula is a ▲ mathematical formula, chemical formula, table, etc. A liquid crystal compound characterized by being represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617179A JPS6043058B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617179A JPS6043058B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5679647A JPS5679647A (en) | 1981-06-30 |
| JPS6043058B2 true JPS6043058B2 (en) | 1985-09-26 |
Family
ID=15621894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15617179A Expired JPS6043058B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6043058B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH055716Y2 (en) * | 1988-12-13 | 1993-02-15 | ||
| JPH055714Y2 (en) * | 1988-12-02 | 1993-02-15 | ||
| JPH055715Y2 (en) * | 1988-12-02 | 1993-02-15 | ||
| JPH0510446Y2 (en) * | 1989-01-09 | 1993-03-15 | ||
| JPH0510445Y2 (en) * | 1989-01-09 | 1993-03-15 | ||
| JPH0513074Y2 (en) * | 1989-01-09 | 1993-04-06 | ||
| JPH0513073Y2 (en) * | 1988-12-13 | 1993-04-06 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3039735B2 (en) * | 1991-11-12 | 2000-05-08 | キヤノン株式会社 | Liquid crystal compound, liquid crystal composition containing the same, liquid crystal element having the same, display method and display device using the same |
| CN103131426B (en) * | 2011-11-25 | 2014-08-20 | 达兴材料股份有限公司 | Liquid crystal compound and liquid crystal medium |
| CN102660297B (en) * | 2012-04-12 | 2013-12-04 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and its display device |
-
1979
- 1979-11-30 JP JP15617179A patent/JPS6043058B2/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH055714Y2 (en) * | 1988-12-02 | 1993-02-15 | ||
| JPH055715Y2 (en) * | 1988-12-02 | 1993-02-15 | ||
| JPH055716Y2 (en) * | 1988-12-13 | 1993-02-15 | ||
| JPH0513073Y2 (en) * | 1988-12-13 | 1993-04-06 | ||
| JPH0510446Y2 (en) * | 1989-01-09 | 1993-03-15 | ||
| JPH0510445Y2 (en) * | 1989-01-09 | 1993-03-15 | ||
| JPH0513074Y2 (en) * | 1989-01-09 | 1993-04-06 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5679647A (en) | 1981-06-30 |
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