JPS6043057B2 - liquid crystal compound - Google Patents
liquid crystal compoundInfo
- Publication number
- JPS6043057B2 JPS6043057B2 JP15617079A JP15617079A JPS6043057B2 JP S6043057 B2 JPS6043057 B2 JP S6043057B2 JP 15617079 A JP15617079 A JP 15617079A JP 15617079 A JP15617079 A JP 15617079A JP S6043057 B2 JPS6043057 B2 JP S6043057B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- acid
- chloro
- crystal compound
- 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 17
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WIPYZRZPNMUSER-UHFFFAOYSA-N 2-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1Cl WIPYZRZPNMUSER-UHFFFAOYSA-N 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 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
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- -1 ester compounds Chemical class 0.000 description 2
- OUPVLTDSUUIXEK-UHFFFAOYSA-N 2-chloro-4-(4-hexylbenzoyl)oxybenzoic acid Chemical compound C1=CC(CCCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C(Cl)=C1 OUPVLTDSUUIXEK-UHFFFAOYSA-N 0.000 description 1
- CPEPWESLFZVUEP-UHFFFAOYSA-N 4-hexylbenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C=C1 CPEPWESLFZVUEP-UHFFFAOYSA-N 0.000 description 1
- XRAHLPNMIIAEPP-UHFFFAOYSA-N 4-hexylbenzoyl chloride Chemical compound CCCCCCC1=CC=C(C(Cl)=O)C=C1 XRAHLPNMIIAEPP-UHFFFAOYSA-N 0.000 description 1
- UMKXSOXZAXIOPJ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2-naphthol Chemical compound C1CCCC2=CC(O)=CC=C21 UMKXSOXZAXIOPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000004043 responsiveness Effects 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 中でも、ネマチック液晶の有する電気光学効果。1 Smectic liquid crystal 2 Nematic liquid crystal 3 Cholesteric liquid crystal Among them, the electro-optic effect of nematic liquid crystals.
−欅Ｐを利用した表示体技術の進歩は著しく、時計、電
・卓などの表示部に液晶表示体が使用されているのは周
知のとうりである。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。- Display technology using Keyaki P has made remarkable progress, and it is well known that liquid crystal displays are used in the display parts of watches, calculators, desks, etc. 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
により改善でき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４〜６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 is a straight-chain alkyl group having 4 to 6 or 8 carbon atoms or 6
represents a straight-chain alkoxy group having 5 carbon atoms.
）で表わされる、２−クロロー４（ｐ−ｎ−アルキルベ
ンゾイルオキシ）安息香酸２−（５，６，７，８−テト
ラヒドロナフチル）エステル、及び２−クロロー４一（
ｐ−ｎ−アルコキシベンゾイルオキシ）安息香酸２−（
５，６，７，８−テトラヒドロナフチル）エステル類で
あり、下記の方法に従つて製造できる。ＳｔｅＰｌ：市
販の２−クロロー４−ヒドロキシ安息香酸と、市配の５
，６，７，８−テトラヒドロー２−ナフトールをトルエ
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、２−クロロー４ヒドロキシ安息香酸２−（５，
６，７，８−テトラヒドロナフチル）エステルを得る。
Ｓｔｅｐ２：市販のｐ−ｎ−アルキル安息香酸、又はア
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、又はｐ−ｎ−アルコキ
シ安息香酸クロライドを得る。), 2-chloro-4(p-n-alkylbenzoyloxy)benzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester, and 2-chloro-4-(
p-n-alkoxybenzoyloxy)benzoic acid 2-(
5,6,7,8-tetrahydronaphthyl) esters, and can be produced according to the method below. StePl: commercially available 2-chloro-4-hydroxybenzoic acid and commercially available 5
, 6,7,8-tetrahydro-2-naphthol was esterified in toluene in the presence of sulfuric acid and boric acid as a catalyst to obtain 2-chloro-4hydroxybenzoic acid 2-(5,
6,7,8-tetrahydronaphthyl) ester is obtained.
Step 2: Commercially available p-n-alkylbenzoic acid or alkoxybenzoic acid is reacted with thionyl chloride to form p-n
-Alkylbenzoic acid chloride or p-n-alkoxybenzoic acid chloride is obtained.
Ｓｔｅｐ３：ＳｔｅｐｌとＳｔｅＰ２で得た両者の化合
物をエステル化し、係わる２−クロロー４−（ｐ−ｎ−
アルキルベンゾイルオキシ）安息香酸２−（５，６，７
，８−テトラヒドロナフチル）エステル及び２−クロロ
ー４−（ｐ−ｎ−アルコキシベンゾイルオキシ）安息香
酸２−（５，６，７，８−テトラヒドロナフチル）エス
テルを得る。Step 3: Both compounds obtained in Stepl and SteP2 are esterified, and the related 2-chloro-4-(p-n-
alkylbenzoyloxy)benzoic acid 2-(5,6,7
, 8-tetrahydronaphthyl) ester and 2-chloro 4-(p-n-alkoxybenzoyloxy)benzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester.
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。The method for producing the compound provided by the present invention will be described in more detail below with reference to Examples.
実施例１
ｓｔｅＰ１：２−クロロー４−ヒドロキシ安息香酸１１
．７ｇをトルエン６００ｍ１に溶解し、この溶液に５，
６，７，８−テトラヒドロー２−ナフトール１０ｙ，硫
酸０．２ｍ１，硼酸０．２ｙをそれぞれ加え、３０時間
還流下に加熱した。Example 1 steP1: 2-chloro-4-hydroxybenzoic acid 11
．． Dissolve 7g in 600ml of toluene and add 5,
10 y of 6,7,8-tetrahydro-2-naphthol, 0.2 ml of sulfuric acid, and 0.2 y of boric acid were added, and the mixture was heated under reflux for 30 hours.
反応後、トルエンを留去し、残つた粗２−クロロー４−
ヒドロキシ安息香酸２−（５，６，７，８−テトラヒド
ロナフチル）エステルを、アセトニトリル、及びメタノ
ールにより再結晶製取した。Ｍｐｌ３８〜１４０しＣ
該化合物の赤外線吸光図を第１図に示す。After the reaction, toluene was distilled off and the remaining crude 2-chloro-4-
Hydroxybenzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester was recrystallized from acetonitrile and methanol. Mpl38-140C The infrared absorption diagram of this compound is shown in FIG.
ＳｔｅＰ２：市販のｐ−ｎ−ヘキシル安息香酸２０．７
ｖと塩化チオニル３０ｍｔをガスの発生が止むまで還流
下に加熱した。SteP2: Commercially available p-n-hexylbenzoic acid 20.7
V and 30 mt 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−ヘキシル安息香酸クロライドを製取した。Ｂｐ
ｌＯ７〜１１０℃／０．５瓢Ｈｙ
Ｓｔｅｐ３：Ｓｔｅｐｌで得た２−クロロー４−ヒドロ
キシ安息香酸２−（５，６，７，８−テトラヒドロナフ
チル）エステル０．５ｙをピリジン１０ｍ１に溶解した
溶液に、ＳｔｅＰ２で得たｐ−ｎ−ヘキシル安息香酸ク
ロライド０．３７ｙを加え、よく混合した後、■時間室
温に放置した。After refluxing, excess thionyl chloride was distilled off, and pn-hexylbenzoic acid chloride was produced by distillation under reduced pressure. Bp
lO7~110℃/0.5 Hy , 0.37 y of p-n-hexylbenzoic acid chloride obtained in SteP2 was added, mixed well, and then left at room temperature for 1 hour.
放置後、この混合液を氷片を浮べた冷濃塩酸中に注加し
、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。Ｍｐ３７Ｃｃｐ７７Ｃ該化合物の赤外線吸光図を
第２図に示す。After being allowed to stand, this mixed solution was poured into cold concentrated hydrochloric acid topped with ice chips, and the separated and precipitated crystals were collected and recrystallized from hexane. The infrared absorption diagram of the compound Mp37Ccp77C is shown in FIG.
こうして、係わる２−クロロー４−（ｐ−ｎ−ヘキシル
ベンゾイルオキシ）安息香酸２−（５，６，７，８−テ
トラヒドロナフチル）エステルを得た。In this way, the related 2-chloro-4-(p-n-hexylbenzoyloxy)benzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester was obtained.
実施例２〜５
又、実施例１と同様にして、前記２−クロロー４−ヒド
ロキシ安息香酸２−（５，６，７，８−テトラヒドロナ
フチル）エステルと、表１に示すＮＯ．２〜５の酸クロ
ライドを製造し、エステル化を行ない表２に示すＮＯ．
２″〜５″の液晶性化合物を製造した。Examples 2 to 5 In addition, in the same manner as in Example 1, the 2-chloro-4-hydroxybenzoic acid 2-(5,6,7,8-tetrahydronaphthyl) ester and the NO. Acid chlorides 2 to 5 were produced and esterified to obtain the NO.
A liquid crystalline compound having a size of 2" to 5" was produced.
尚、本発明に係わる表２のＮＯ．２″〜５″の液晶性化
合物の赤外線吸光図を第３〜６図に示す。Note that No. 2 in Table 2 related to the present invention. The infrared absorption diagrams of liquid crystalline compounds of 2" to 5" are shown in FIGS. 3 to 6.
本発明によつて提供されるエステル化合物は、表−２に
示す温度範囲の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 in the temperature range shown in Table 2.
これらの液晶性化合物は、１アプライド・フィジックス
レターズ（ＡｐｐＩｉｅｄＰｈｙｓｉｃｓレＴｔｅｂ
）ＶＯｌ、２＼陥．４、１９７祥８月１５日Ｊ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、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 1 Applied Physics Letters.
) VOl, 2\fall. 4, August 15, 197 J. et al. as a liquid crystal material for dual-frequency drive liquid crystal displays, and also as liquid crystal compositions used in various liquid crystal displays when mixed with existing liquid crystal compounds. Can be used as one material.
第１図〜第６図は、下記の化合物のそれぞれ赤外線吸光
図を示す。Figures 1 to 6 show infrared absorption diagrams of the following compounds, respectively.
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。 ）で表か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, a chemical formula, a table, etc.▼ (wherein R is a straight-chain alkyl group having 4 to 6 or 8 carbon atoms or a straight-chain alkyl group having 6 carbon atoms) A liquid crystal compound characterized by being represented by a chain alkoxy group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617079A JPS6043057B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617079A JPS6043057B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5679646A JPS5679646A (en) | 1981-06-30 |
| JPS6043057B2 true JPS6043057B2 (en) | 1985-09-26 |
Family
ID=15621873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15617079A Expired JPS6043057B2 (en) | 1979-11-30 | 1979-11-30 | liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6043057B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0293859U (en) * | 1989-01-12 | 1990-07-25 |
-
1979
- 1979-11-30 JP JP15617079A patent/JPS6043057B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0293859U (en) * | 1989-01-12 | 1990-07-25 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5679646A (en) | 1981-06-30 |
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