JPH03215454A - Ester derivative - Google Patents
Ester derivativeInfo
- Publication number
- JPH03215454A JPH03215454A JP2006757A JP675790A JPH03215454A JP H03215454 A JPH03215454 A JP H03215454A JP 2006757 A JP2006757 A JP 2006757A JP 675790 A JP675790 A JP 675790A JP H03215454 A JPH03215454 A JP H03215454A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- formulas
- tables
- 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
- 150000002148 esters Chemical class 0.000 title claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 17
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- -1 n-hebutyl Chemical group 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- HXBKPYIEQLLNBK-UHFFFAOYSA-N 4-(4-octylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HXBKPYIEQLLNBK-UHFFFAOYSA-N 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 101150030723 RIR2 gene Proteins 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は新規な光学活性エステル誘導体に関するもので
あり、詳しくは液晶化合物、又は液晶組成物の成分とし
て有用な光学活性エステル誘導体に関するものである。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a novel optically active ester derivative, and more particularly to an optically active ester derivative useful as a component of a liquid crystal compound or a liquid crystal composition. .
（従来の技術）
液晶化合物が電気光学表示装置に利用されて以来、数多
くの液晶化合物が合成され、ネマチック液晶またはネマ
チックーコレステリンク液晶が、ねじれネマチックモー
ド表示素子、コレステリックーネマチンク相転移現象利
用表示素子またはゲスト・ホスト効果利用表示素子など
に広く利用されている。(Prior Art) Since liquid crystal compounds were used in electro-optical display devices, many liquid crystal compounds have been synthesized, including nematic liquid crystals or nematic-cholesterink liquid crystals, twisted nematic mode display elements, and cholesteric-nematic phase transition phenomena. It is widely used in display devices or display devices that utilize the guest-host effect.
しかし、これらの表示素子の応答速度は最高でも数ｍｓ
ｅｃのオーダーであり、この点が液晶表示素子の応用範
囲をせばめる一因となっている。However, the response speed of these display elements is several ms at most.
It is on the order of ec, and this point is one of the reasons for narrowing the range of applications of liquid crystal display elements.
最近になり強誘電性を示す液晶すなわち強誘電性液晶を
用いると、μｓｅｃオーダーの高速で応答が得られると
いうことがわかって来た。Recently, it has been found that when a liquid crystal exhibiting ferroelectric properties, that is, a ferroelectric liquid crystal, is used, a response can be obtained at a high speed on the order of μsec.
従来知られている強誘電性液晶の例としては、１９７５
年にＲ．Ｂ．Ｍｅｙｅｒらにより合成された４−（４’
−ｎ一デシルオキシベンジリデンアミノ）ケイ皮酸−２
−メチルブチルエステル（以下、ＤＯＢＡＭＢＣと記す
）が挙げられ、該ＤＯＢＡＭＢＣは、そのカイラルスメ
クチックＣ相（以下、ＳｍＣ”と記す）において強誘電
性を示すことを特徴としている（Ｊ．Ｐｈｙｓｉｑｕｅ
．３６ Ｌ−６９ （１９７５））。An example of a conventionally known ferroelectric liquid crystal is the 1975
R. B. 4-(4'
-n-decyloxybenzylidene amino)cinnamic acid-2
-Methyl butyl ester (hereinafter referred to as DOBAMBC), which is characterized by exhibiting ferroelectricity in its chiral smectic C phase (hereinafter referred to as "SmC") (J. Physique
．． 36 L-69 (1975)).
１９８０年になりＮ．Ａ．ＣｌａｒｋらがＤｏＢＡＭＢ
Ｃを使用した薄膜セルにおいてμｓｅｃオーダーの高速
応答を見い出して以来（Ａｐｐｌ．ｐｈｙｓ．Ｌｅｔｔ
．３６ ８９ （１９８０））多くの、強誘電性液晶
の合成研究がなされて来たが、現状では、
（１）室温で液晶状態であるのは勿論のこと、低温から
高温までの出来るだけ広い範囲で強誘電性液晶状態を示
すこと、
（２）水分、空気、光、熱等に対して安定であること、
（３） 自発分極が大きく低粘性であること、（４）
応答速度の速いこと、
（５） 駆動電圧の低いこと、
等の物性的要求の全てを単一化合物で満たす強誘電性液
晶化合物はなく、何種類かの強誘電性液晶化合物を組み
合せた組成物として強誘電性液晶表示素子に使用するこ
とによって目的を達している。In 1980, N. A. Clark et al. DoBAMB
Since discovering a high-speed response on the μsec order in a thin film cell using C (Appl.phys.Lett
．． 36 89 (1980)) Many studies have been conducted on the synthesis of ferroelectric liquid crystals, but at present, (1) they are not only in a liquid crystal state at room temperature, but also in a wide range from low to high temperatures; (2) be stable against moisture, air, light, heat, etc.; (3) have large spontaneous polarization and low viscosity; (4)
There is no single ferroelectric liquid crystal compound that satisfies all physical requirements such as fast response speed and (5) low driving voltage, but a composition that combines several types of ferroelectric liquid crystal compounds is needed. This goal has been achieved by using it in ferroelectric liquid crystal display devices.
（発明が解決しようとする課Ｈ）
本発明の目的は前記の強誘電性液晶表示素子材料として
好適な新規な光学活性エステル誘導体を提供するもので
ある。(Problem H to be Solved by the Invention) An object of the present invention is to provide a novel optically active ester derivative suitable as the above-mentioned ferroelectric liquid crystal display element material.
（課題を解決するための手段）
すなわち、本発明は、下記一般式（１）で表わされる光
学活性エステル誘導体を要旨とするものである。(Means for Solving the Problems) That is, the gist of the present invention is an optically active ester derivative represented by the following general formula (1).
｛式中、Ｒｌは炭素数２〜１８のアルキル基、炭素数２
〜１８のアルコキシ基または
Ｒ３÷０＋ＣＨｚｈ±ＴＯ−｛Ｒ３は炭素数１〜ｌ５の
アルキル基を示し、ｍは２又は３を示し、ｎは、１また
は２を示す。〕を示し、Ｒｚは、炭素数２を示す。｝
以下に本発明を詳細に説明する。{In the formula, Rl is an alkyl group having 2 to 18 carbon atoms, 2 carbon atoms
~18 alkoxy group or R3÷0+CHzh±TO-{R3 represents an alkyl group having 1 to 15 carbon atoms, m represents 2 or 3, and n represents 1 or 2. ], and Rz represents 2 carbon atoms. } The present invention will be explained in detail below.
本発明のエステル誘導体は、前記一殻式（１）で表わさ
れ、式中、ＲｌおよびＲｚで表わされるアルキル基とし
ては、炭素数２〜１８の直鎖又は分岐鎖状のアルキル基
が挙げられ、好ましくはｎプロピル、ｎ−プチル、ｓｅ
ｃ−ブチル、ｉｓｏ−ブチル、２−メチルブチル、ｎ−
ペンチル、ｎ−ヘキシル、ｎ−へブチル、ｎ−オクチル
、ｎ−ノニル、ｎ−デシル、ｎ−ウンデシル、ｎ−ドデ
シル等の炭素数３〜ｌ２のアルキル基が挙げられる。The ester derivative of the present invention is represented by the one-shell formula (1), in which the alkyl groups represented by Rl and Rz include straight chain or branched alkyl groups having 2 to 18 carbon atoms. preferably n-propyl, n-butyl, se
c-butyl, iso-butyl, 2-methylbutyl, n-
Examples include alkyl groups having 3 to 12 carbon atoms such as pentyl, n-hexyl, n-hebutyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl.
Ｒ１で表わされるアルコキシ基としては、上記アルキル
基に相当するアルコキシ基が挙げられる。Examples of the alkoxy group represented by R1 include alkoxy groups corresponding to the alkyl groups described above.
Ｒ３としては、直鎖または分岐鎖状の炭素数１〜１５の
アルキル基が挙げられ、好ましくはメチル、エチル、ｎ
−プロビル、ｎ−ブチル、ＳｅＣ〜ブチル、ｉｓｏ
７’チル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチル
、ｎ−オクチル、ｎ−ノニル、ｎ−デシル、ｎ−ウンデ
シル、ｎ−ドデシル等の炭素数１〜ｌ２のアルキル基が
挙げられる。Examples of R3 include linear or branched alkyl groups having 1 to 15 carbon atoms, preferably methyl, ethyl, n
-proyl, n-butyl, SeC ~ butyl, iso
Examples include alkyl groups having 1 to 12 carbon atoms such as 7'thyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl.
ハロゲン原子で置換された＋Ａ＋とじては、れる。+A+ substituted with a halogen atom is .
本発明のエステル誘導体は例えば、次の反応により合成
することが出来る。The ester derivative of the present invention can be synthesized, for example, by the following reaction.
（ＩＶ）
（一般式Ｃｌｌ）， （．Ｉ［）および（ＩＶ）中の
ＲＩＲ２，＋Ａ＋は前記一般式（１）におけると同意義
を示す。）
上記反応中■の反応は、例えば塩化チオニル中、７０〜
１００゜Ｃで反応することにより、実施することが出来
る。(IV) (General formula Cll), (.I[) and RIR2, +A+ in (IV) have the same meanings as in the above general formula (1). ) In the above reaction (2), for example, in thionyl chloride, 70 to
This can be carried out by reacting at 100°C.
上記反応中■の反応は、例えばピリジン中、あるいはジ
オキサン、テトラヒド口フラン等のエーテル系溶媒また
はベンゼン、トルエン等の芳香族炭化水素系溶媒中、ピ
リジン、キノリン、トリエチルアミン、トリエチレンジ
アミン等のアミン系脱酸剤または炭酸ナトリウム、炭酸
カリウム、重炭酸ナトリウム等の無機系脱酸剤の存在下
で、例エハ、１０〜１５０゜Ｃの温度で反応することに
より、実施することが出来る。The reaction (2) in the above reaction is carried out, for example, in pyridine, or in an ether solvent such as dioxane, tetrahydrofuran, or an aromatic hydrocarbon solvent such as benzene or toluene. The reaction can be carried out in the presence of an acid agent or an inorganic deoxidizing agent such as sodium carbonate, potassium carbonate, sodium bicarbonate, etc., at a temperature of 10 to 150°C.
本発明に係る工′ステル誘導体の具体例として、例えば
以下の第１表のものを挙げることが出来る。Specific examples of the ester derivatives according to the present invention include those in Table 1 below.
本発明のエステル誘導体は、単独であっても、それらの
混合物であっても液晶化合物として用いることができ、
更には、適当な公知の液晶化合物と組み合せても使用す
ることができ、本発明のエステル誘導体を混合すること
により高温部の液晶温度範囲の広い液晶組成物を得るこ
とが出来る。The ester derivatives of the present invention can be used alone or as a mixture of them as a liquid crystal compound,
Furthermore, it can be used in combination with an appropriate known liquid crystal compound, and by mixing the ester derivative of the present invention, a liquid crystal composition having a wide liquid crystal temperature range in the high temperature region can be obtained.
かかる公知の液晶化合物としては、エステル系、ジエス
テル系、アゾキシ系、アゾ系、シッフ系、ピリミジン系
、ビフェニル系、フェニルシクロヘキサン系、シクロへ
キシルシク口ヘキサン系、ビシクロオクタン系、ジオキ
サン系あるいは、ベンゼン環、シクロヘキサン環より成
る多環化合物系等が挙げられる。Such known liquid crystal compounds include ester, diester, azoxy, azo, Schiff, pyrimidine, biphenyl, phenylcyclohexane, cyclohexane, bicyclooctane, dioxane, and benzene ring compounds. , a polycyclic compound system consisting of a cyclohexane ring, and the like.
更に、本発明において液晶組成物を形成する場合、公知
の二色性色素、光安定化剤あるいは滅粘剤等の添加剤を
併用することが出来る。Furthermore, when forming a liquid crystal composition in the present invention, known additives such as dichroic dyes, light stabilizers, or thinners can be used in combination.
（実施例）
次に、本発明を実施例により更に具体的に説明するが、
本発明は、以下の実施例に限定されるものではない。(Example) Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited to the following examples.
実施例１
一般式（１）においてＲ’ ＝ ＯＣｓＨ＋７ｔ−＋
で表わされる化合物（第１表、Ｎｏ． １の化合物）の
合成。Example 1 In general formula (1), R' = OCsH+7t-+
Synthesis of the compound represented by (Table 1, compound No. 1).
４′−ｎ−オクチルオキシビフェニル−４−カルポン酸
０．１９ｇに塩化チオニル１０ｃｃを加え、２時間加熱
還流した後、過剰の塩化チオニルを滅圧下留去し、４′
−ｎ−オクチルオキシビフェニル−４−カルボン酸塩化
物を得た。10 cc of thionyl chloride was added to 0.19 g of 4'-n-octyloxybiphenyl-4-carboxylic acid, and after heating under reflux for 2 hours, excess thionyl chloride was distilled off under reduced pressure.
-n-octyloxybiphenyl-4-carboxylic acid chloride was obtained.
この塩化物全量をトルエン１０ｃｃに溶解した溶〔一般
式（ＩＶ）でＲ２＝Ｃ６Ｈｌ：ｌ （ｎ）；［αｌ”
１ ６．８ ４’ （ Ｃ Ｏ．６ １，
ＣＨＣｆｆｉｉ））０． ２ ２ ｇ 及びトリエチ
レンジアミン０．２ｇｔｌトルエン２ ０ｍｆに溶解し
た溶液中に滴下する。２０〜２５℃で７時間撹拌した後
、水１ ０ ０ｃａｌ及びクロロホルム５０ｌｌＩ１．
を加える。分離した有機層を、６Ｎ一塩酸、次いで５％
炭酸ナトリウム水溶液で洗浄し、更に中性になるまで水
洗する。A solution in which the entire amount of this chloride was dissolved in 10 cc of toluene [in the general formula (IV), R2=C6Hl:l (n); [αl”
1 6.8 4' (C O.6 1,
CHCffii))0. 22 g and triethylenediamine 0.2 gtl dissolved in 20 mf toluene are added dropwise. After stirring at 20-25°C for 7 hours, 100 cal of water and 50 liters of chloroform were added.
Add. The separated organic layer was washed with 6N monohydrochloric acid, then 5%
Wash with an aqueous sodium carbonate solution and then with water until neutral.
有機層を無水硫酸ナトリウムで乾燥し、溶媒を留去後シ
リカゲル力ラムクロマトグラフィーにより精製すること
により、目的の下記の式？表わされるエステル誘導体０
． ０ ７ ｇを得た。The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and then purified by silica gel column chromatography to obtain the desired formula ? Ester derivative represented 0
．． 0.7 g was obtained.
［α］２４−７． ６ ２゜ （Ｃ Ｏ．３１， Ｃ
ＨＣｌ３）ＩＲ （ＫＢｒ）：２９５０，２８７０，１
７６０，１７４０，１６１０，１５１０，
１３００，１２８０，１２００，
１１４０．１０８０ ９２０ｃｍ−’元素分析値（％
） Ｃ ： ７ ３． ０ ９ Ｈ ： ７． １
２Ｃ４■Ｈ ａ ｑ Ｏ ｓ Ｆ ：ｌとしての計算値
（％）Ｃ：７３．０２ Ｈ：７．１５
この化合物の相転移温度は以下のごとくである。[α]24-7. 6 2゜ (C O.31, C
HCl3)IR (KBr):2950,2870,1
760,1740,1610,1510, 1300,1280,1200, 1140.1080 920cm-'Elemental analysis value (%
) C: 7 3. 0 9 H: 7. 1
2C4■H a q O s F: Calculated value (%) as l C: 73.02 H: 7.15 The phase transition temperature of this compound is as follows.
（但し、 Ｃ ｒｙは結晶相、 Ｓｃ″ はスメクチックＳｃ＊ 相、 Ｓ＾ はスメクチックＡ相、 ｃｈはコレステリ ック相、 ■よ。は等方性液体を示す。(however, Cry is a crystalline phase, Sc″ is smectic Sc* phase, S^ is smectic A phase, ch is cholesteri lock phase, ■Yo. indicates an isotropic liquid.
） を得、 無水酢酸でアセチル化後、 常法により 更に常法により、 脱アセチル化して得た。) obtained, After acetylation with acetic anhydride, by the usual method Furthermore, according to the usual method, Obtained by deacetylation.
実施例２
一般式（１）においてＲ’ ＝−Ｃ．Ｈ．，。，で表わ
される化合物（第１表、Ｎα３の化合物）の合成。Example 2 In general formula (1), R' = -C. H. ,. , (Table 1, compound Nα3).
実施例ｌで使用した４′−ｎ−オクチルオキシビフェニ
ル−４−カルボン酸０．２ｇの代りに、４′−ｎ−オク
チルビフェニル−４−カルボン酸０．１８ｇを使用し、
他は同様に処理して、目的の下記の式
で表わされるエステル誘導体０．１０ｇを得た。Instead of 0.2 g of 4'-n-octyloxybiphenyl-4-carboxylic acid used in Example 1, 0.18 g of 4'-n-octylbiphenyl-4-carboxylic acid was used,
The rest was treated in the same manner to obtain 0.10 g of the desired ester derivative represented by the following formula.
［α］” −８．０ １’ （Ｃ Ｏ．４ １，
ＣＨＣ／！！）ＩＲ （ＫＢｒ） ：２９８０
， ２９００， １７８０，元素分析値
（％）
１７６０， １６２０． １４Ｂ０，１３００．
１２１０， １１７０．１ １００． ９００
ｃｍ−’
Ｃ：７４．８０ Ｈ：７．２８
？４■Ｈ．．Ｏ．Ｆ１としての計算値（％）Ｃ：７４。[α]" -8.0 1' (CO.4 1,
CHC/! ! )IR (KBr): 2980
, 2900, 1780, elemental analysis value (%) 1760, 1620. 14B0,1300.
1210, 1170.1 100. 900
cm-' C: 74.80 H: 7.28? 4■H. ．． O. Calculated value (%) C as F1: 74.
７５ Ｈ：７．３２ この化合物の相転移温度は以下のごとくである。75 H:7.32 The phase transition temperature of this compound is as follows.
（但し、Ｃ ｒｙは結晶相、ＳＡはスメクチックＡ相、
ｃｈはコレステリック相をＩ３。は等方性液体を示す。(However, Cry is crystalline phase, SA is smectic A phase,
ch is cholesteric phase I3. indicates an isotropic liquid.
）
実施例３〜ｌ５
実施例１に準じた方法で第２表に示す一般式［Ｉ）の化
合物を得た。それらの元素分析値を示す。) Examples 3 to 15 Compounds of general formula [I] shown in Table 2 were obtained by a method according to Example 1. Their elemental analysis values are shown.
第
２
表
（発明の効果）
本発明化合物は液晶テレビ等のディスプレイ、光プリン
ターヘッド、光フーリエ変換素子、ライトバルブ等に使
用する強誘電性液晶化合物又は組成物用成分として有用
である。Table 2 (Effects of the Invention) The compounds of the present invention are useful as ferroelectric liquid crystal compounds or components for compositions used in displays such as liquid crystal televisions, optical printer heads, optical Fourier transform elements, light valves, and the like.
Claims (1)
２〜１８のアルコキシ基または ▲数式、化学式、表等があります▼〔Ｒ＾３は炭素数１
〜１５の アルキル基を示し、ｍは２又は３を示し、ｎは、１また
は２を示す。〕を示し、Ｒ＾２は、炭素数２〜１８のア
ルキル基を示し、▲数式、化学式、表等があります▼は
▲数式、化学式、表等があります▼，▲数式、化学式、
表等があります▼（Ｘは水素原子またはハロゲン 原子を示す。），▲数式、化学式、表等があります▼，
▲数式、化学式、表等があります▼ または▲数式、化学式、表等があります▼を示し、Ｃ＾
＊は不斉炭素 を示す。｝で表わされる光学活性エステル誘導体。[Claims] General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] {In the formula, R^1 is an alkyl group having 2 to 18 carbon atoms, Alkoxy group or ▲ Numerical formula, chemical formula, table, etc. ▼ [R^3 is carbon number 1
~15 alkyl groups, m represents 2 or 3, and n represents 1 or 2. ], R^2 represents an alkyl group having 2 to 18 carbon atoms, ▲ has mathematical formulas, chemical formulas, tables, etc. ▼ has ▲ mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼ (X indicates a hydrogen atom or a halogen atom), ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼,
Indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, C^
* indicates an asymmetric carbon. } Optically active ester derivative represented by.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006757A JPH03215454A (en) | 1990-01-16 | 1990-01-16 | Ester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006757A JPH03215454A (en) | 1990-01-16 | 1990-01-16 | Ester derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03215454A true JPH03215454A (en) | 1991-09-20 |
Family
ID=11647055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006757A Pending JPH03215454A (en) | 1990-01-16 | 1990-01-16 | Ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03215454A (en) |
-
1990
- 1990-01-16 JP JP2006757A patent/JPH03215454A/en active Pending
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