JPH0269443A - Fluoroalkyl based compound and liquid crystal composition - Google Patents
Fluoroalkyl based compound and liquid crystal compositionInfo
- Publication number
- JPH0269443A JPH0269443A JP22083588A JP22083588A JPH0269443A JP H0269443 A JPH0269443 A JP H0269443A JP 22083588 A JP22083588 A JP 22083588A JP 22083588 A JP22083588 A JP 22083588A JP H0269443 A JPH0269443 A JP H0269443A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- liquid crystal
- compound expressed
- compound
- phase
- 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.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 title abstract description 59
- 125000003709 fluoroalkyl group Chemical group 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 fluoroalkyl compound Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 4
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 31
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 8
- 230000001747 exhibiting effect Effects 0.000 abstract description 7
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 6
- 239000005711 Benzoic acid Substances 0.000 abstract description 5
- 235000010233 benzoic acid Nutrition 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910019213 POCl3 Inorganic materials 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- AMVHMKULOHFQSB-UHFFFAOYSA-N 4-(4-octoxybenzoyl)oxybenzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C=C1 AMVHMKULOHFQSB-UHFFFAOYSA-N 0.000 description 2
- HFRUPPHPJRZOCM-UHFFFAOYSA-N 4-octoxyphenol Chemical compound CCCCCCCCOC1=CC=C(O)C=C1 HFRUPPHPJRZOCM-UHFFFAOYSA-N 0.000 description 2
- QDOAWUCLBBYAGY-UHFFFAOYSA-N 4-phenylmethoxycarbonylcyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C(=O)OCC1=CC=CC=C1 QDOAWUCLBBYAGY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JTCRQLVSMPPNJI-MXVIHJGJSA-N O=C([C@@H]1CC[C@H](CC1)C(=O)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 Chemical compound O=C([C@@H]1CC[C@H](CC1)C(=O)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 JTCRQLVSMPPNJI-MXVIHJGJSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- WCJLKAOWUBVWSG-UHFFFAOYSA-N 2-octoxybenzoyl chloride Chemical compound CCCCCCCCOC1=CC=CC=C1C(Cl)=O WCJLKAOWUBVWSG-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- RGRIMQYNCUGNDQ-UHFFFAOYSA-N 4-phenylmethoxycarbonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)OCC1=CC=CC=C1 RGRIMQYNCUGNDQ-UHFFFAOYSA-N 0.000 description 1
- 102100022096 Acid-sensing ion channel 5 Human genes 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HXTYZWJVMWWWDK-IZLXSQMJSA-N ClC(=O)[C@H]1CC[C@@H](CC1)C(Cl)=O Chemical compound ClC(=O)[C@H]1CC[C@@H](CC1)C(Cl)=O HXTYZWJVMWWWDK-IZLXSQMJSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101000901085 Homo sapiens Acid-sensing ion channel 5 Proteins 0.000 description 1
- VWFWJPJMAFRNET-MQWMPURMSA-N IACI Chemical compound C1=CC=C2C([C@@H](O)[C@@H]3CC4CCN3C[C@@H]4CC)=CC=NC2=C1NC(=O)C1=CC([125I])=C(N=[N+]=[N-])C=C1O VWFWJPJMAFRNET-MQWMPURMSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- TUMHNADUCFXBLP-UHFFFAOYSA-N OC(C(C=C1)=CC=C1C(OCC1=CC=CC=C1)=O)=O.Cl Chemical compound OC(C(C=C1)=CC=C1C(OCC1=CC=CC=C1)=O)=O.Cl TUMHNADUCFXBLP-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical group C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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】
（イ）産業上の利用分野
この発明は新規なフルオロアルキル系化合物およびそれ
を含有してなる液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Industrial Application Field This invention relates to a novel fluoroalkyl compound and a liquid crystal composition containing the same.
（ロ）従来の技術
現在液晶表示素子ではネマチック液晶相を利用等の化合
物が知られている（ Ｍｏ１．Ｃｒｙｓｔ、ＬｉｇＣｒ
ｙｓｔ、、１１０巻（１９８４年）１７５頁）。(b) Conventional technology Compounds that utilize a nematic liquid crystal phase are currently known for liquid crystal display elements (Mo1.Cryst, LigCr).
yst, vol. 110 (1984) p. 175).
（ハ）発明が解決しようとする課題
使用する液晶に望まれる性質は表示モードによって異な
るが、現在のところ単一化合物で望まれる条件を総て満
たすことは不可能であり、複数の化合物を混合して実用
に供している。このため実用可能な条件を満たす液晶組
成物を作成するためには多様な性質をもった数多くの単
品液晶化合物が必要となる。また、それ自身液晶性を示
さない化合物が液晶組成物の成分として有用となる可能
性もある。(c) Problems to be Solved by the Invention The desired properties of the liquid crystal used differ depending on the display mode, but at present it is impossible to satisfy all the desired conditions with a single compound, so a mixture of multiple compounds is required. and put it into practical use. Therefore, in order to create a liquid crystal composition that satisfies practical conditions, a large number of single liquid crystal compounds with diverse properties are required. Additionally, compounds that do not themselves exhibit liquid crystal properties may be useful as components of liquid crystal compositions.
これまて数多くの液晶化合物が合成されてきたが、良好
な特性を示す液晶組成物の開発に必要な新規な化合物の
開発は依然として強く望まれている。とりわけスメクチ
ック液晶組成物用の化合物を数多く創出することが今後
必要である。Although a large number of liquid crystal compounds have been synthesized, there is still a strong desire to develop new compounds necessary for developing liquid crystal compositions exhibiting good properties. In particular, it is necessary in the future to create a large number of compounds for smectic liquid crystal compositions.
また、スメクチックＣ相を利用した強誘電性液晶組成物
においては、ノン・カイラル液晶化合物よりなる室温で
スメクチックＣ相を呈する液晶組成物と光学活性化合物
とを混合することにより強誘電性液晶組成物を作成する
方式が近年主流になって来ており、この点からもスメク
チックＣ相を呈する化合物の開発が望まれている。強誘
電性液晶組成物においては、これに加えて、ＩＡＣＩ
Ｎ Ａ Ｃ（Ｉｓｏｔｒｏｐｉｃ−Ｎｅｍａｔｉｃ−３
ｍｅｃＬｉｃ＾−３ｍｅｃｔｉｃ Ｃ）という相系列を
呈する必要があり、この観点からも様々な転移温度を示
す多数のスメクチック液晶化合物の創出が望まれている
。In addition, in a ferroelectric liquid crystal composition using a smectic C phase, a ferroelectric liquid crystal composition is prepared by mixing a liquid crystal composition made of a non-chiral liquid crystal compound that exhibits a smectic C phase at room temperature with an optically active compound. In recent years, the method of producing smectic C phase has become mainstream, and from this point of view as well, the development of compounds exhibiting a smectic C phase is desired. In addition to this, in the ferroelectric liquid crystal composition, IACI
NAC (Isotropic-Nematic-3
It is necessary to exhibit a phase series called mecLic^-3mectic C), and from this point of view as well, it is desired to create a large number of smectic liquid crystal compounds that exhibit various transition temperatures.
この発明はこのような状況下なされたものであり、スメ
クチック相を利用した表示に用いる液晶組成物の構成成
分として有用なフルオロアルキル系化合物及び液晶組成
物を提供することを目的とするものである。The present invention was made under these circumstances, and it is an object of the present invention to provide a fluoroalkyl compound and a liquid crystal composition useful as constituent components of a liquid crystal composition used for display utilizing a smectic phase. .
（ニ）課題を解決するための手段
この発明によれば、−数式
（ただし、Ｒは炭素数１〜１５のアルキル基、Ａｍは１
又は２、ｎは１〜１５の整数を示す）で表わされるフル
オロアルキル系化合物が提供さメｔろ。(d) Means for Solving the Problems According to the present invention, the formula (where R is an alkyl group having 1 to 15 carbon atoms, Am is 1
or 2, n represents an integer of 1 to 15).
上記式（１）の化合物は、文献未記載の化合物である。The compound of formula (1) above is a compound that has not been described in any literature.
上記式におけるＲ（炭素数１〜１５のアルキル基）には
、メチル、エチル、プロピル、ｉ−プロピル、ブチル、
ｉ−ブチル、ペンチル、ｌ−又は２メチルブチル、ヘキ
シル、１−又は３−メチルペンチル、ヘプチル、１−又
は４−メチルヘキシル、オクチル、１−メチルヘプチル
、ノニル、！−又は６−メチルオクチル、デシル、■−
メチルノニル、ウンデシル、■−メチルデシル、ドデシ
ル、ｌ−メチルウンデシル等が含まれる。これらのアル
キル基中で炭素鎖に不斉炭素が含まれていてもよい。R (alkyl group having 1 to 15 carbon atoms) in the above formula includes methyl, ethyl, propyl, i-propyl, butyl,
i-butyl, pentyl, l- or 2-methylbutyl, hexyl, 1- or 3-methylpentyl, heptyl, 1- or 4-methylhexyl, octyl, 1-methylheptyl, nonyl, ! - or 6-methyloctyl, decyl, -
Includes methylnonyl, undecyl, -methyldecyl, dodecyl, l-methylundecyl and the like. The carbon chain of these alkyl groups may contain an asymmetric carbon.
この発明のフルオロアルキル系化合物は、上記ができる
。The fluoroalkyl compound of this invention can do the above.
まず、この発明の式（Ｉａ）で表わされるフルオロアル
キル系化合物は、例えば下記反応式（１）〜（５）で表
わされるステップによって合成することができる。すな
わち、ｐ−アルコキシ安息香酸と５塩化リンとを反応さ
せて、ｐ−アルコキン安息香酸クロリドを得（１）、こ
れにｐ−ヒドロキン安息香酸ベンジルエステルを反応さ
せて、４−（４′−アルコキノーベンゾイルオキシ）安
吉、香酸ベンジルエステルを合成しく２）、次のこの化
合物をＰｄ−Ｃを用いて水素添加して４−（４′−アル
コキシ−ベンゾイルオキシ）安息香酸を得（３）、さら
にこれを五塩化リンと反応させて４−（４’−アルコキ
ン−ヘンジイルオキシ）安い、香酸クロリドにかえた（
４）後、パーフルオロアルカノールと反応させる（５）
ことにより得られる。First, the fluoroalkyl compound represented by the formula (Ia) of the present invention can be synthesized, for example, by steps represented by the following reaction formulas (1) to (5). That is, p-alkoxybenzoic acid and phosphorus pentachloride are reacted to obtain p-alcoquine benzoic acid chloride (1), and p-hydroquine benzoic acid benzyl ester is reacted with this to obtain 4-(4'-alcokyne benzoic acid chloride). quinobenzoyloxy) Yasuyoshi, fragrant benzyl ester was synthesized (2), and then this compound was hydrogenated using Pd-C to obtain 4-(4'-alkoxy-benzoyloxy)benzoic acid (3), This was further reacted with phosphorus pentachloride to convert it to 4-(4'-alcokyne-hendiyloxy), a cheap aromatic acid chloride (
4) After that, react with perfluoroalkanol (5)
It can be obtained by
（以下余白）
で表すことができ、例えば次の通り合成すること（ただ
し、
Ｒは炭素数１から１
５のアルキル基を示す）
タル酸モノベンジルエステルと５塩化リンとを反応させ
て、テレフタル酸モノベンジルエステルクロリドを得（
６）、これにパーフルオロアルカノールを反応させて、
ベンジルパーフルオロアルキルテレフタレートを得（７
）、次のこの化合物にＰｄ−Ｃを用いて水素添加してテ
レフタル酸モノパーフルオロアルキルエステルを得（８
）、さらにこれを五塩化リンと反応させてテレフタル酸
モノパーフルオロアルキルエステルクロリドに変え（９
）、次いで、ｐ−アルコキシフェノールと反応させる（
ＩＱ）ことにより得られる。For example, it can be synthesized as follows (where R represents an alkyl group having 1 to 15 carbon atoms).Terephthalate can be synthesized by reacting monobenzyl talic acid ester with phosphorus pentachloride. Acid monobenzyl ester chloride is obtained (
6), by reacting this with perfluoroalkanol,
Benzyl perfluoroalkyl terephthalate was obtained (7
), this compound was then hydrogenated using Pd-C to obtain terephthalic acid monoperfluoroalkyl ester (8
) and further reacted with phosphorus pentachloride to convert it into terephthalic acid monoperfluoroalkyl ester chloride (9
), then reacted with p-alkoxyphenol (
IQ).
（以下余白）
（Ｉａ）
（ただし、ｍはｌ又は２、ｎはＩ−１５の整数）この発
明の式（ｒｂ）で表わされるフルオロアルキル系化合物
は、例えば、下記反応式（６）〜（１０）で表わされる
方法によって合成され、まずテレフ（ただし、
示す）
（ただし、
ｍはｌ又は２、
ｎは１〜！５の整数を
（Ｉｂ）
Ｒは炭素数ｌ〜１
５のアルキル基を示
また、この発明の式（ＩＣ）で表わされるフルオロアル
キル系化合物は、例えば次のような（１１）〜（１８）
で表わされるステップで合成される。まず、トランス−
１，４−シクロへキシルジカルボン酸と５塩化リンとを
反応させて、トランス−１，４−シクロへキシルジカル
ボン酸ジクロリドを得（１１）、これにベンジルアルコ
ールを反応させてトランス−１，４−シクロへキシルジ
カルボン酸ジベンジルエステルを合成（１２）する。次
のこの化合物をＰｄ−Ｃを用いて水素添加してトランス
−１，４−シクロへキシルジカルボン酸モノベンジルエ
ステルに変え（１３）、さらにこれを五塩化リンと反応
させてトランス−１，４−シクロへキシルジカルボン酸
モノベンジルエステルクロリドに変え（１４）、これと
Ｐ−アルコキシフェノールとを反応させてＰ−アルコキ
シフェニルベンジル トランス−１，４−シクロへキシ
ルジカルボキシレートを得る（１５）。次いで、この化
合物をＰｄ−Ｃを用いて水素添加してトランス−１，４
−シクロへキシルジカルボン酸モノ（Ｐ−アルコキシ）
フェニルエステルを得（１６）、さらにこれを五塩化リ
ンと反応させてトランス−１，４−シクロへキシルジカ
ルボン酸モノ（Ｐ−アルコキシ）フェニルエステルクロ
リドに変え（１７）、これをパーフルオロアルカノール
と反応させることにより化合物（Ｉｃ）を得る（１８）
ことができる。(The following is a blank space) (Ia) (However, m is l or 2, and n is an integer of I-15) The fluoroalkyl compound represented by the formula (rb) of this invention can be used, for example, in the following reaction formulas (6) to ( It is synthesized by the method expressed by In addition, the fluoroalkyl compounds represented by formula (IC) of the present invention include, for example, the following (11) to (18).
It is synthesized in the steps represented by . First, trans-
Trans-1,4-cyclohexyldicarboxylic acid dichloride was obtained by reacting 1,4-cyclohexyldicarboxylic acid with phosphorus pentachloride (11), and trans-1,4-cyclohexyldicarboxylic acid dichloride was obtained by reacting this with benzyl alcohol. -Synthesize (12) cyclohexyldicarboxylic acid dibenzyl ester. This compound was then hydrogenated using Pd-C to convert it to trans-1,4-cyclohexyldicarboxylic acid monobenzyl ester (13), which was further reacted with phosphorus pentachloride to form trans-1,4-cyclohexyldicarboxylic acid monobenzyl ester. -Cyclohexyldicarboxylic acid monobenzyl ester chloride (14) and reacted with P-alkoxyphenol to obtain P-alkoxyphenylbenzyl trans-1,4-cyclohexyldicarboxylate (15). This compound was then hydrogenated using Pd-C to form trans-1,4
-Cyclohexyldicarboxylic acid mono(P-alkoxy)
The phenyl ester was obtained (16), which was further reacted with phosphorus pentachloride to convert it into trans-1,4-cyclohexyldicarboxylic acid mono(P-alkoxy) phenyl ester chloride (17), which was converted to perfluoroalkanol. Compound (Ic) is obtained by reaction (18)
be able to.
（ただし、Ｒは炭素数１〜１５のアルキル基を示す）（
Ｉａ）
（たたし、ｍは１又は２、ｎはｌ−１５の整数を示す）
この発明の式（１）で表わされる化合物はそれ自体安定
なスメクチックＡ相及びＣ相を示すので、この発明の化
合物を用いてスメクチックＡｔ目又：よスメクチックＣ
相を示す液晶組成物を作ることかできる。かかる液晶組
成物は、通常この発明のフルオロアルキル系化合物を０
１〜３０重量％、スメクチックＣ相を呈する他の液晶化
合物又は液晶組成物を７０〜９９．９重量％を配合して
作製することかでき、特にスメクチックＣ相を呈する他
の液晶化合物又は液晶組成物と組み合わせて強誘電性液
晶表示装置に利用する液晶組成物を作成する場合、式（
１）の化合物はスメクチックＣ相の広い温度範囲を確保
できると共に、スメクチックＣ相の上にスメクチックＡ
相を出現させてＩＮＡＣｌＩＡＣなどの相系列を有する
液晶組成物を作成することができる。なお、上記液晶組
成物はこの発明のフルオロアルキル系化合物を１種含有
してもよいが、２種以上含有してもよい。(However, R represents an alkyl group having 1 to 15 carbon atoms) (
Ia) (where m is 1 or 2 and n is an integer of 1-15) Since the compound represented by formula (1) of this invention itself shows stable smectic A phase and C phase, this Smectic Atmata using the compound of the invention: Yosmectic C
It is possible to create liquid crystal compositions that exhibit phases. Such liquid crystal compositions usually contain 0 of the fluoroalkyl compounds of the present invention.
1 to 30% by weight, and 70 to 99.9% by weight of other liquid crystal compounds or liquid crystal compositions exhibiting a smectic C phase, particularly other liquid crystal compounds or liquid crystal compositions exhibiting a smectic C phase. When creating a liquid crystal composition to be used in a ferroelectric liquid crystal display device in combination with
The compound 1) can ensure a wide temperature range of the smectic C phase, and also has smectic A on top of the smectic C phase.
Phases can appear to create liquid crystal compositions having a phase series such as INAClIAC. The liquid crystal composition may contain one type of fluoroalkyl compound of the present invention, or may contain two or more types.
上記式（＋）で表わされるこの発明の化合物の中でも、
式（Ｉａ）で表わされるものとしては特にＣ山ｏ−＠−
ｃｏｏや−ＣＯＯ−ＣＢ、−Ｃ，Ｆ。Among the compounds of this invention represented by the above formula (+),
Among those represented by formula (Ia), C mountain o-@-
coo and -COO-CB, -C,F.
Ｃ山Ｏ舎Ｃ００（ツーＣ０Ｏ−ＣＨｔＣＨｔ−ＣｓＦ＋
−Ｃ４Ｈ＠０ラーＣＯＯ＠ Ｃ０Ｏ−ＣＨｔＣＨ２−Ｃ
ｌ ２ＦＭＳＣ，）１．．０台ｃｏｏ−：防Ｃｏｏ−Ｃ
ＩＩ＊ＣＨ＊ −Ｃ，ＰＩｃ、ｎ、、ｏ−４防ｃｏｏ−
４ンＣｏｏ−ＣＨ，−Ｃ，Ｆ、。C mountain O building C00 (two C0O-CHtCHt-CsF+
-C4H@0rahCOO@C0O-CHtCH2-C
l 2FMSC,)1. ．． 0 units coo-: Anti-Coo-C
II*CH* -C, PIc, n,, o-4 prevention coo-
4-Coo-CH, -C,F,.
ＣＪ、＋、０＜防ＣＯＯ舎Ｃｏｏ−ＣＨ＊ＣＨｔ−Ｃ４
Ｆ＊ｓＣ３山、０（ツーＣｏｏ＠−ＣＯＯ−ＣＩ、ＣＨ
，−Ｃ，Ｆ。CJ, +, 0<Coo-CH*CHt-C4
F*sC3 mountain, 0 (Two Coo@-COO-CI, CH
, -C,F.
ｃ、山、ｏ−（つ−ｃｏｏ−４ラーＣｏｏ−ＣＨ，ＣＨ
，−Ｃ，Ｆ、。c, mountain, o-(tsu-coo-4rahCoo-CH,CH
,-C,F,.
か、式（１ｂ）て表シつされるものとしては特にｃｏｔ
ｏ −イ（三］＝＝巨仁）←ＯＣＯ＋Ｃｏｏ ＣＨｔ
ＣＩｌｙ Ｃ−ＦｍＣＨ，Ｏ−※０ＣＯ（シＣｏｏ−
Ｃｌ１．ＣＩ＋、−Ｃ，Ｆ、ワＣ，Ｉ＋、叶◎−ｏｃｏ
＋ｃｏｏ−ｃ＋＋、 −Ｃ，Ｆ。In particular, as expressed by formula (1b), cot
o −I (three) == Giant) ← OCO + Coo CHt
CIly C-FmCH, O-*0CO (Coo-
Cl1. CI+, -C, F, wa C, I+, Kano◎-oco
+coo-c++, -C,F.
Ｃ山ｏ−（トＯＣＯ＜ンＣ０Ｏ−ＣＩｌｆ−活ｃ、ｏ、
ｏ−＠ｏｃｏ−（：刻Ｃｏｏ ＣＩＬ＋ＣＨｙ Ｃ５Ｆ
ｌ ？Ｃ，Ｉ＋、０−■ｏｃｏ＋ｃｏｏ−ｃｏ、ｃｏ、
−Ｃ，、Ｆ、。C mountain o-(ToOCO<nC0O-CIlf-active c, o,
o-@oco-(:KokuCoo CIL+CHy C5F
l? C, I+, 0-■oco+coo-co, co,
-C,,F,.
Ｃ＊１ＬｔＯ−◎−ｏｃｏ＋ｃｏｏ ＣＨｔＣＩＩｙ
Ｃ４Ｆ＠Ｃ品０÷ＯＣＯ＋ＣＯＯ−ＣＨ，−Ｃ，Ｆ、。C*1LtO-◎-oco+coo CHtCIIy
C4F@C product 0÷OCO+COO-CH, -C,F.
Ｃ，Ｉ＋、、Ｏ−◇→ｃｏ＋ｃｏｏ Ｃｌ１２ＣＩＩｚ
−Ｃ＋ｔＦ＊ｓＣ＋ ＊ＨｔｓＯ＋ＯｃＯ＋ｃＯｏ Ｃ
ＨｅＣ）１ｇ −Ｃ，ＦｅＯ２山、０−（コ辷０ＣＯ−
／４ｆｆＣＯＯ−ＣＨ，ＣＩ、−Ｃ，Ｆ、？Ｃ３，１晴
０−Ｑ＋、’−０（Ｏ（す’、−Ｃｏｏ Ｃ１ｌ ｔ
−Ｃ１−Ｆ ｒ ｓ−、−］
が、式（Ｉｃ）で表わされるものとしては特にＣＯコ０
−〈ひ−ｏｃｏ−＼′−ソＣｏｏ−−ＣＩｌＩＣＨ，−
ＣＪ、？−□
ＣｓＨ＋７０ ＜、Ｉ、工ろ、−ｏｃｏ−べ、−−７と
−ＣＯＯＣＨ，−ＣＪｓＣ，Ｈ，ヤ０インｏｃｏ０ｃｏ
ｏ−ｃｏ、ｃｕ、−Ｃ，、Ｆ、。C, I+,, O-◇→co+coo Cl12CIIz
-C+tF*sC+ *HtsO+OcO+cOo C
HeC) 1g -C, FeO2 mountain, 0-(ko辷0CO-
/4ffCOO-CH,CI,-C,F,? C3,1 0-Q+,'-0(O(su',-Coo C1l t
-C1-F r s-,-] is particularly represented by the formula (Ic).
-〈Hi-oco-\'-SoCoo--CIlICH,-
C.J.? -□ CsH+70 <, I, engineering, -oco-be, -7 and -COOCH, -CJsC,H, ya 0in oco0co
o-co, cu, -C,,F,.
かスメクチックＡ相またはスメクチックＣ相を利用する
液晶材料を作る場合に好ましい。This is preferred when producing a liquid crystal material that utilizes a smectic A phase or a smectic C phase.
一方、スメクチックＣ相を呈する他の液晶化合物と組み
合わ仕て用いる場合、組み合わせる対象の液晶としては
当該分野で知られｊ＝種々の化合物があり、その具体例
としては下式（ＩＩ）、Ｕ）、（ＩＶ）で示される化合
物か挙げられる。もちろん、これらは２種以上混合して
用いることができる。On the other hand, when used in combination with other liquid crystal compounds exhibiting a smectic C phase, there are various compounds known in the art as liquid crystals to be combined, where j = various compounds, specific examples of which are the following formulas (II), U) , (IV). Of course, two or more of these can be used in combination.
Ｒ−ａ−Ｑ−ｏ−αＢ−Ｒ’ （ＩＩ）Ｒ−
ｃ−Ｑ−ｏ−＠−＋＠−Ｂ−Ｒ゛（ｍ）Ｒ−ｃ−（ｏ）
、−ｐ−Ｑ−（ｃＮ）Ｂ−Ｒ′（ＴＶ）（式中、Ｇ及び
Ｂは、それぞれ、単結合、またはＣＯＯ−−０ＣＯ−−
ＣＨ＝、ＣＨ−ＣＯＯ−−０ＣＯ−ＣＩｌＣＨ−−０−
−３−−０ＣＯＯ−もしくは−〇〇−の基を示す。Ｄ及
びＥは、それぞれ、単結合、又はＣＯＯ−−０ＣＯ−−
Ｃ）Ｉ＝Ｎ−−八＝ＣＨ−−ＣＨ＝ＣＨ−−ＣミＣ−−
ＣＨ＝ＣＨ１−ＣＯＯ−７０ＣＯ−ＣＨ＝ＣＨＣＬＣＬ
０ＣＨ２ＣＬＯ−ＣＯ３−もしくは−８ＣＯ−
の基を示す。■、■及び■はそ２−それ独立して、ベン
ゼン環、シクロヘキサン環、ビシクロ［２，２，２］オ
クタン環、ピリジン環、ピリミジン環、ピラジン環、ピ
リダジン環、ピペラジン環、ピラン環、ジオキサシクロ
ヘキサン環、チアピラン環、ジチアン環、チアンアジン
環、テトラジン環などの六員環を示し、これらの六員環
中の水素原子はフッ素原子、塩素原子、臭素原子、シア
ノ基、ニトロ基、低級アルキル基、低級アルコキシ基、
又は重水素で置換されてもよい。Ｒ及びＲ′はそれぞれ
独立して、直鎖状または分岐状で炭素数１ ＝ １５の
アルキル基を示し、アルキル基中に不斉炭素が含まれて
いてもよい。ｐはｌ又は２の整数を示す。）
（ホ）実施例
実施例１
４−（４′−オクチルオキシ−ベンゾイルオキシ）安息
香酸ＩＨＩＨ２Ｈ２Ｈ−パーフルオロヘキシルエステル
の合成（式（Ｉ ａ）においてＲ＝ Ｃｓ Ｈ１７、ｍ
＝２、ｎ＝４）
オクチルオキン安息香酸５．１ｇ（０，０２０ｍｏｌ
）に１．１倍当量の五塩化リンを加え、約８０℃に加熱
して反応させる。反応後、減圧蒸留によってＰＯＣｌ３
および過剰の５塩化リンを完全に除去し、オクチルオキ
シ安息香酸クロリドを得る。これをトルエン４０ｒｎＱ
に溶解し、さらにＰ−ヒドロキシ安息香酸ベンジルエス
テル５．６９（０，０２４ｍｏｌ ）とピリジン４０１
とを加えて室温で１０時間放置した後、６０℃に加温し
、そのまま３時間保ってから冷却する。その後、塩酸に
加え、エーテルで抽出する。エーテル層をＮａＨＣＯｓ
水溶液で洗浄し、次いで水で洗い、Ｎａ＊ＳＯａで乾燥
する。エーテルを留去し、残留物をカラムクロマトグラ
フィーで精製し、クロロホルムとエタノールとの混合溶
媒から再結晶して４−（４′オクチルオキシ−ベンゾイ
ルオキシ）安息香酸ベンジルエステル７．６９（収率７
８％）を得た。この化合物の融点は６５℃であった。R-a-Q-o-αB-R' (II)R-
c-Q-o-@-+@-B-R゛(m)R-c-(o)
, -p-Q-(cN)B-R'(TV) (wherein G and B are each a single bond or COO--0CO--
CH=, CH-COO--0CO-CIlCH--0-
-3--0COO- or -〇〇- group. D and E are each a single bond or COO--0CO--
C) I=N--8=CH--CH=CH--CmiC--
CH=CH1-COO-70CO-CH=CHCLCL
0CH2CLO-CO3- or -8CO-
Indicates the group of ■, ■, and ■ are independently benzene ring, cyclohexane ring, bicyclo[2,2,2]octane ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, piperazine ring, pyran ring, Indicates six-membered rings such as oxacyclohexane ring, thiapyran ring, dithian ring, thianazine ring, and tetrazine ring, and hydrogen atoms in these six-membered rings are fluorine atoms, chlorine atoms, bromine atoms, cyano groups, nitro groups, and lower alkyl groups. group, lower alkoxy group,
Alternatively, it may be substituted with deuterium. R and R' each independently represent a linear or branched alkyl group having 1=15 carbon atoms, and an asymmetric carbon may be included in the alkyl group. p represents an integer of l or 2. ) (e) Examples Example 1 Synthesis of 4-(4'-octyloxy-benzoyloxy)benzoic acid IHIH2H2H-perfluorohexyl ester (in formula (I a), R= Cs H17, m
= 2, n = 4) Octyl oxine benzoic acid 5.1 g (0,020 mol
) was added with 1.1 equivalents of phosphorus pentachloride and heated to about 80°C to react. After the reaction, POCl3 is extracted by vacuum distillation.
and excess phosphorus pentachloride is completely removed to obtain octyloxybenzoic acid chloride. Add this toluene 40rnQ
Furthermore, P-hydroxybenzoic acid benzyl ester 5.69 (0,024 mol) and pyridine 401
After adding and leaving at room temperature for 10 hours, the mixture was heated to 60°C, maintained at that temperature for 3 hours, and then cooled. Then, it is added to hydrochloric acid and extracted with ether. ether layer with NaHCOs
Wash with aqueous solution, then water and dry with Na*SOa. The ether was distilled off, the residue was purified by column chromatography, and recrystallized from a mixed solvent of chloroform and ethanol to give benzyl 4-(4'octyloxy-benzoyloxy)benzoic acid ester 7.69 (yield 7).
8%). The melting point of this compound was 65°C.
次に、４− （４′オクチルオキシーベンゾイルオキン
）安息香酸ベンジルエステル７．６９を１１？のＰｄ−
Ｃを含むトルエンｘｏｏ１！ｃと酢酸１００ｍ（との混
合溶液に溶かし、この溶液を真空脱気し、さらに容器内
に水素を挿入し、撹拌する。水素添加によって得られｔ
：４−（４′オクチルオキシ−ベンゾイルオキシ）安息
香酸をカラムクロマトグラフィーによって精製し、エタ
ノールで再結晶した。収量４．７ｇ（収率８０％）。こ
の化合物の相転移は１４７℃ １７４℃ ２３９
℃
Ｃ−−→５ｃ−−→Ｎ−−→ ■
（ここでＣ，Ｓｃ、Ｎ、Ｉはそれぞれ結晶相、スメクチ
ックＣ相、ネマチック相、等方性液体を示す。）
であった。Next, 4-(4'octyloxy-benzoyluoquine)benzoic acid benzyl ester 7.69 was added to 11? Pd-
Toluene containing C xoo1! Dissolve t in a mixed solution of c and 100 m of acetic acid, vacuum degas the solution, add hydrogen into the container, and stir.T obtained by hydrogenation.
:4-(4'octyloxy-benzoyloxy)benzoic acid was purified by column chromatography and recrystallized from ethanol. Yield: 4.7 g (yield: 80%). The phase transition of this compound is 147℃ 174℃ 239
℃ C--→5c--→N--→ (Here, C, Sc, N, and I each indicate a crystalline phase, a smectic C phase, a nematic phase, and an isotropic liquid.)
得られた４−（４’オクチルオキシ−ベンゾイルオキシ
）安息香酸０．５９（０，００１４ｍｏ＋）に１，１倍
当量の五塩化リンを加え０、約８０℃で加熱して反応さ
せる。減圧蒸留によってＰＯＣｌ、および過剰の５塩化
リンを完全に除去し、４−（４’−才クチルオキシ−ベ
ンゾイルオキシ）安息香酸クロリドを得る。To 0.59 (0,0014 mo+) of the obtained 4-(4'octyloxy-benzoyloxy)benzoic acid was added 1.1 times equivalent of phosphorus pentachloride, and the mixture was heated at about 80° C. to react. POCl and excess phosphorus pentachloride are completely removed by vacuum distillation to obtain 4-(4'-cutyloxy-benzoyloxy)benzoic acid chloride.
これをトルエン１０ｊ１１２に溶解し、さらにＩＨＩ）
１２Ｈ２Ｈ−パーフルオロヘキサノール０．４３９ （
０，００１６ｍｏｌ ）とピリジン２０ｍＱとを加える
。室温で１０時間放置しに後、６０℃に加温し、そのま
ま３時間保ってから冷却する。その後、塩酸に加え、エ
ーテルで抽出する。エーテル層をＮａｔｌＣＯａ水溶液
、次いて水で洗い、Ｎａ＝ＳＯ，で乾燥する。エーテル
を留去し、残留物をカラムクロマトグラフィーで精製し
、トルエンとエタノールとの混合溶媒から再結晶して４
− （４’オクチルオキシ−ベンゾイルオキシ）安息香
酸１１１１）＋２Ｈ２Ｈ−パーフルオロヘキシルエステ
ル０．３６９（収率４３％）を得た。この化合物の転移
温度を第１表に示す。また、この化合物の赤外スペクト
ルを第１図に示す。Dissolve this in toluene 10j112 and further IHI)
12H2H-perfluorohexanol 0.439 (
0,0016 mol) and 20 mQ of pyridine are added. After being left at room temperature for 10 hours, the mixture was heated to 60°C, maintained for 3 hours, and then cooled. Then, it is added to hydrochloric acid and extracted with ether. The ether layer is washed with an aqueous solution of NatlCOa, then water, and dried over Na=SO. The ether was distilled off, the residue was purified by column chromatography, and recrystallized from a mixed solvent of toluene and ethanol.
-(4'octyloxy-benzoyloxy)benzoic acid 1111)+2H2H-perfluorohexyl ester 0.369 (yield 43%) was obtained. The transition temperature of this compound is shown in Table 1. Moreover, the infrared spectrum of this compound is shown in FIG.
実施例２
実施例１の合成法に準じて第１表に示す７種の化合物を
合成し、得られた化合物の転移温度を第１表に示す。Example 2 Seven kinds of compounds shown in Table 1 were synthesized according to the synthesis method of Example 1, and the transition temperatures of the obtained compounds are shown in Table 1.
（以下余白）
実施例３
４−才クチルオキシフェニル−ＩＨＩＨ２Ｈ２Ｈ−パー
フルオロヘキシルテレフタレートの合成（式％式％）
テレフタル酸モノベンジルエステル２．０９（０，ＯＱ
７８ｍｏｌ ）に１．１倍当量の五塩化リンを加え、約
８０℃で加熱して反応させる。減圧蒸留によってＰＯＣ
ｌ２および過剰の５塩化リンを完全に除去し、テレフタ
ル酸モノベンジルエステルクロリドを得る。これをトル
エン１０ｍＱに溶解し、さらにＬＨＩＨ２Ｈ２Ｈ−パー
フルオロヘキサノール２．５９（０，００９３ｍｏｌ
）とピリジンＩＤｙｔ（ｌとを加える。室温で１０時間
放置した後、６０℃に加温し、そのまま３時間保ってか
ら冷却する。その後、塩酸に加え・、エーテルで抽出す
る。エーテル層をＮａＨｅＯｓ水溶液、次いで水で洗い
、
ｒｉａｔｓＯ４で乾燥する。エーテルを留去し、残留物
をカラムクロマトグラフィーで精製し、エタノールから
再結晶してベンジル−ＩＨＩＨ２Ｈ２Ｈ−パーフルオロ
ヘキシルテレフタレート ３．１９ （収率８９％）ヲ
得た。(Space below) Example 3 Synthesis of 4-year-old ctyloxyphenyl-IHIH2H2H-perfluorohexyl terephthalate (formula % formula %) Terephthalic acid monobenzyl ester 2.09 (0, OQ
78 mol) was added with 1.1 equivalents of phosphorus pentachloride and heated at about 80°C to react. POC by vacuum distillation
12 and excess phosphorus pentachloride are completely removed to obtain terephthalic acid monobenzyl ester chloride. This was dissolved in 10 mQ of toluene, and 2.59 (0,0093 mol) of LHIH2H2H-perfluorohexanol was added.
) and pyridine IDyt (l). After leaving at room temperature for 10 hours, warm to 60°C, keep as it is for 3 hours, and then cool. Then, add to hydrochloric acid and extract with ether. The ether layer is diluted with NaHeOs. Wash with aqueous solution, then with water and dry over riatsO4. The ether was distilled off and the residue was purified by column chromatography and recrystallized from ethanol to give benzyl-IHIH2H2H-perfluorohexyl terephthalate 3.19 (yield 89%). ) I got it.
次に、得られたベンジル−ＩＨＩＨ２）１２）１−パー
フルオロヘキシル−テレフタレート３．０９をＶ９のＰ
ｄ−Ｃを含むトルエン１００ＭＱと酢酸１０ｈ（！との
混合溶液に溶かし、この溶液を真空脱気し、さらに容器
内に水素を挿入し撹拌する。水素添加によって得られた
テレフタル酸モノＩＨＩＨ２１（２Ｈ−パーフルオロア
ルキルエステルをカラムクロマトグラフィーによって精
製し、エタノールトルエン混合溶媒で再結晶した。収量
２．０９ （収率８０％）。この化合物の融点は１８９
℃であった。Next, 3.09 of the obtained benzyl-IHIH2)12)1-perfluorohexyl-terephthalate was added to P of V9.
Dissolve in a mixed solution of 100MQ of toluene and 10h of acetic acid (!) containing d-C, vacuum degas the solution, and then add hydrogen into the container and stir.Terephthalic acid mono IHIH21 (2H - The perfluoroalkyl ester was purified by column chromatography and recrystallized from a mixed solvent of ethanol and toluene. Yield: 2.09 (yield: 80%). The melting point of this compound was 189
It was ℃.
得られたテレフタル酸モノＩＨ１）１２１１２１１−パ
ーフルオロアルキルエステル０．５９（０，００１４ｍ
ｏｌ ）に１．１倍当量の五塩化リンを加え、約８０℃
で加熱して反応させる。減圧蒸留によってＰＯＣｌ３お
よび過剰の５塩化リンを完全に除去し、テレフタル酸モ
ノＩＨ１１１２Ｈ２１１−パーフルオロアルキルエステ
ルクロリドを得る。これをトルエン１０ｘＱに溶解し、
さらに４−オクチルオキシフェノール０．３７＋１ （
０，００１７ｍｏｌ）とピリジン１０ｔｔｒＱとを加え
る。室温で１０時間放置した後、６０℃に加温し、その
まま３時間保ってから冷却する。その後、塩酸に加え、
エーテルで抽出するエーテル層をＮａＨｅＯｓ水溶液、
次いで水で洗い、ＮａｔＳＯ＋で乾燥する。エーテルを
留去し、残留物をカラムクロマトグラフィーで精製し、
トルエンとエタノールとの混合溶媒から再結晶して４−
オクチルオキシフェニル−ＩＨＩＨ２１（２Ｈ−パーフ
ルオロヘキシルテレフタレート０．３ｈ（収率４９％）
を得ｒこ。The obtained terephthalic acid mono IH1) 1211211-perfluoroalkyl ester 0.59 (0,0014 m
1.1 equivalent of phosphorus pentachloride was added to 80°C
Heat and react. POCl3 and excess phosphorus pentachloride are completely removed by vacuum distillation to obtain terephthalic acid mono IH1112H211-perfluoroalkyl ester chloride. Dissolve this in toluene 10xQ,
Furthermore, 4-octyloxyphenol 0.37+1 (
0,0017 mol) and 10 ttrQ of pyridine are added. After being left at room temperature for 10 hours, the mixture was heated to 60°C, maintained for 3 hours, and then cooled. Then add hydrochloric acid,
The ether layer extracted with ether is extracted with NaHeOs aqueous solution,
Then wash with water and dry with NatSO+. The ether was distilled off, the residue was purified by column chromatography,
Recrystallize from a mixed solvent of toluene and ethanol to obtain 4-
Octyloxyphenyl-IHIH21 (2H-perfluorohexyl terephthalate 0.3h (yield 49%)
Get it.
この化合物の転移温度を第２表に示す。また、この化合
物の赤外スペクトルを第２図に示す。The transition temperature of this compound is shown in Table 2. Moreover, the infrared spectrum of this compound is shown in FIG.
実施例４
４−オクチルオキシフェニル−Ｉ １１１ ）１−パー
フルオロプロピル−トランス−１，４−シクロヘキサン
カルボキシレートの合成（式（Ｉ ｃ）においてＲ−Ｃ
，Ｈ，、、ｍ＝Ｉ、ｎ＝２）
トランス−１，４−シクロヘキサンジカルボン酸１０、
ｈ （０，０５８ｍｏｌ ）に五塩化リン１５．９９（
０，１３３ｍｏｌ）を加え、約８０℃で加熱して反応さ
せる。減圧蒸留によってＰＯＣｌ、および過剰の５塩化
リンを完全に除去し、トランス−１，４−シクロヘキサ
ンジカルボン酸クロリドを得る。これをトルエン１０ｍ
＋２に溶解し、さらにベンジルアルコール１３．８ｇ（
０，１３９ｍ０１）とピリジン１（Ｌ！１２とを加える
。室温で１０時間放置した後、６０℃に加温し、そのま
ま３時間保ってから冷却する。その後、塩酸に加え、エ
ーテルで抽出する。エーテル層をＮａＨＣＯｓ水溶液、
次いて水で洗い、ＮａｔＳＯ４で乾燥する。エーテルを
留去し、残留物をカラムクロマトグラフィーで精製し、
エタノールトルエン混合溶媒から再結晶してトランス−
１，４−シクロヘキサンジカルボン酸ジベンジルエステ
ル１６．７１Ｆ （収率８１％）を得た。Example 4 Synthesis of 4-octyloxyphenyl-I 111 ) 1-perfluoropropyl-trans-1,4-cyclohexanecarboxylate (R-C
, H, , m=I, n=2) trans-1,4-cyclohexanedicarboxylic acid 10,
h (0,058 mol) to phosphorus pentachloride 15.99 (
0,133 mol) and heated at about 80°C to react. POCl and excess phosphorus pentachloride are completely removed by vacuum distillation to obtain trans-1,4-cyclohexanedicarboxylic acid chloride. Add this to 10m of toluene
+2 and further add 13.8g of benzyl alcohol (
0,139m01) and pyridine 1 (L!12) are added. After being left at room temperature for 10 hours, the mixture is heated to 60°C, kept as it is for 3 hours, and then cooled. Then, it is added to hydrochloric acid and extracted with ether. The ether layer was treated with NaHCOs aqueous solution,
Then wash with water and dry with NatSO4. The ether was distilled off, the residue was purified by column chromatography,
Recrystallize from ethanol-toluene mixed solvent and trans-
1,4-cyclohexanedicarboxylic acid dibenzyl ester 16.71F (yield 81%) was obtained.
次に、トランス−１，４−シクロヘキサンジカルボン酸
ジベンジルエステルを１９のＰｄ−Ｃを含むトルエン１
００ｍ（と酢酸１００ｍＣとの混合溶液に溶がし、この
溶液を真空脱気し、さらに容器内に水素を挿入し１／３
当景だけ水素添加させる。得られた粗精製物をカラムク
ロマトグラフィーによって分離、精製し、エーテルとヘ
キサン混合溶媒で再結晶して、トランス−１，４−シク
ロヘキサンジカルボン酸モノベンジルエステル２．９９
（収率２３％）を得ｆ二。Next, trans-1,4-cyclohexanedicarboxylic acid dibenzyl ester was added to toluene containing 19 Pd-C.
00mC (and 100mC of acetic acid), vacuum degas the solution, and further insert hydrogen into the container to 1/3
Add hydrogen only to the scene in question. The obtained crude product was separated and purified by column chromatography, recrystallized from a mixed solvent of ether and hexane, and trans-1,4-cyclohexanedicarboxylic acid monobenzyl ester 2.99%
(Yield 23%) f2 was obtained.
この化合物の融点は８２℃であった。The melting point of this compound was 82°C.
、得られたトランス−１，４−シクロヘキサンジカルボ
ン酸モノベンジルエステル２．９９（０，０１０９ｍｏ
ｌ ）に１．１倍当景の五塩化リンを加え、約８０℃で
加熱して反応させる。減圧蒸留によってＰＯＣＩｓおよ
び過剰の５塩化リンを完全に除去し、トランス−１゜４
−シクロヘキサンジカルボン酸モノベンジルエステルク
ロリドを得る。これをトルエン１０Ｒ（ｌに溶解し、さ
らに４−オクチルオキシフェノール２．９ｇ（０，０１
３１ｍｏｌ ）とピリジン１０＊ｆｆとを加える。室温
で１０時間放置した後、６０℃に加温し、そのまま３時
間保ってから冷却する。その後、塩酸に加え、エーテル
で抽出する。エーテル層をＮａＨＣＯｚ水溶液、次いで
水で洗い、ＮａｔＳ０４で乾燥する。エーテルを留去し
、残留物をカラムクロマトグラフィーで精製し、エーテ
ルとヘキサンとの混合溶媒から再結晶して４−オクチル
オキシフェニル−ベンジル−トランス−１，４−シクロ
ヘキサンジカルボキシレート２．ｈ（収率５１％）を得
た。この化合物の融点は４７°Ｃであっ１こ。, the obtained trans-1,4-cyclohexanedicarboxylic acid monobenzyl ester 2.99 (0,0109 mo
Add 1.1 times the same amount of phosphorus pentachloride to (l) and heat at about 80°C to react. POCIs and excess phosphorus pentachloride were completely removed by vacuum distillation, and trans-1°4
- Cyclohexanedicarboxylic acid monobenzyl ester chloride is obtained. This was dissolved in 10R (l) of toluene, and further 2.9g (0.01g) of 4-octyloxyphenol was added.
31 mol) and 10*ff of pyridine are added. After being left at room temperature for 10 hours, the mixture was heated to 60°C, maintained for 3 hours, and then cooled. Then, it is added to hydrochloric acid and extracted with ether. The ether layer is washed with aqueous NaHCOz, then water, and dried over NatS04. The ether was distilled off, the residue was purified by column chromatography, and recrystallized from a mixed solvent of ether and hexane to obtain 4-octyloxyphenyl-benzyl-trans-1,4-cyclohexanedicarboxylate 2. h (yield 51%) was obtained. The melting point of this compound is 47°C.
得られた４−オクチルオキシフェニル−ベンジル−トラ
ンス−１，４−シクロヘキサンジカルボキシレート２．
６９を１９のＰｄ−Ｃを含むトルエン１００＋＋＋Ｑと
酢酸１１００ｊＩの混合溶液に溶かし、この溶液を真空
脱気し、さらに容器内に水素を挿入し撹拌する。Obtained 4-octyloxyphenyl-benzyl-trans-1,4-cyclohexanedicarboxylate2.
69 is dissolved in a mixed solution of toluene 100+++Q and acetic acid 1100jI containing Pd-C of 19, this solution is vacuum degassed, and hydrogen is further introduced into the container and stirred.
水素添加によって得られたトランス−１，４−シクロヘ
キサンノカルボン酸４−オクチルオキシフェニルエステ
ルをカラムクロマトグラフィーによって精製し、アセト
ンで再結晶した。収量０．９９（収率４７％）。Trans-1,4-cyclohexanenocarboxylic acid 4-octyloxyphenyl ester obtained by hydrogenation was purified by column chromatography and recrystallized from acetone. Yield: 0.99 (yield: 47%).
得られたトランス−１，４−７クロヘキサンジカルホ゛
ン酸４−オクチルオキシフェニルエステル０．４９ （
０，０００８６ｍｏｌ）に１．１倍当量の五塩化リンを
加え、約８０℃で加熱して反応させる。減圧蒸留によっ
てＰＯＣｌ３および過剰の５塩化リンを完全に除去し、
トランス−１，４−シクロヘキサンジカルボン酸４−オ
クチルオキシフェニルエステルクロリドを得る。The obtained trans-1,4-7 chlorohexane dicarphonic acid 4-octyloxyphenyl ester 0.49 (
1.1 times equivalent of phosphorus pentachloride is added to 0,00086 mol) and heated at about 80° C. to react. Completely remove POCl3 and excess phosphorus pentachloride by vacuum distillation,
Trans-1,4-cyclohexanedicarboxylic acid 4-octyloxyphenyl ester chloride is obtained.
これをトルエンｌ ０ｔｓＱに溶解し、さらにＩＨＩＩ
Ｉ−パーフルオロプロパツール０．ｌｈ （０，０００
９５ｍｏｌ）とピリジン１０１１１２とを加える。室温
で１０時間放置した後、６０℃に加温し、そのまま３時
間保ってから冷伊する。その後、塩酸に加え、エーテル
で抽出する。エーテル層をｋａＨｃＯ３水溶液、次いで
水で洗い、ＮａｔＳＯ４で乾燥する。エーテルを留去し
、残留物をカラムクロマトグラフィーで精製し、エーテ
ルとヘキサンとの混合溶媒から再結晶して４−オクチル
オキシフェニル−ＩＨＩＨ−パーフルオロプロピル−ト
ランス−１，４−ノクロヘキサンジカルボキシレート０
．１５９（収率２９％）を得た。この化合物７５．０℃
の転移温度はスメクチックＣ相−−−→スフクチ６４．
０°Ｃ
ツクＡ相−Ｍアイソトロピックであった。また、この化
合物の赤外スペクトルを第３図に示す。Dissolve this in toluene l 0tsQ and further IHII
I-Perfluoropropertool 0. lh (0,000
95 mol) and pyridine 101112 are added. After being left at room temperature for 10 hours, it was heated to 60°C, kept as it was for 3 hours, and then cooled. Then, it is added to hydrochloric acid and extracted with ether. The ether layer is washed with aqueous kaHcO3, then water, and dried over NatSO4. The ether was distilled off, the residue was purified by column chromatography, and recrystallized from a mixed solvent of ether and hexane to give 4-octyloxyphenyl-IHIH-perfluoropropyl-trans-1,4-nochlorohexanedicarboxy. rate 0
．． 159 (yield 29%) was obtained. The transition temperature of this compound at 75.0°C is smectic C phase---→smectic 64.
At 0°C, the phase A-M was isotropic. Moreover, the infrared spectrum of this compound is shown in FIG.
実施例５
実施例３に準じて第２表に示す４種の他の化合物を合成
し、得られた化合物の転移温度を第２表に併せて示す。Example 5 Four other compounds shown in Table 2 were synthesized according to Example 3, and the transition temperatures of the obtained compounds are also shown in Table 2.
この発明の化合物はスメクチック液晶性が高く、スメク
チック液晶組成物を得るための構成成分として有用であ
ることが分かる。It can be seen that the compound of this invention has high smectic liquid crystallinity and is useful as a component for obtaining a smectic liquid crystal composition.
（以下余白）
比較例１
ＣＩｂＯ＜＜ ｏｃｏう ｃｏｏ−Ｃｓｌｌ＋ｓ実施
例１のＩＩＩＬＨ２Ｈ２Ｈ−パーフルオロヘキサノール
にかえてヘキサノールを用いるほかは実施例１と同様Ｉ
） 操作＋＝ ヨｒ） 、ＣＩｂ０１◎−ｏｃｏＫうＣ
００−Ｃ＠１１１３を得た。この化合物は液晶相を示さ
なかった（融点５９．０°Ｃ）。(Left below) Comparative Example 1 CIbO
) Operation += Yor), CIb01◎-ocoKuC
00-C@1113 was obtained. This compound did not exhibit a liquid crystal phase (melting point 59.0°C).
（へ）発明の効果
この発明の化合物は安定なスメクチックＡ相及びスメク
チックＣ相を呈するので、スメクチックＡ相ま１こはス
メクチックＣ相を利用する液晶材料を作る場合に有用で
ある。特にスメクチックＣ相を呈する他の液晶化合物と
組み合わせて強誘電性液晶表示装置に利用する液晶組成
物を作成する場合、本発明の化合物はスメクチックＣ相
の上にスメクチックＡ相を出現させてＩＮＡＣ，ＩＡＣ
などの相系列を有する液晶組成物を作成するのに有用で
ある。(f) Effects of the Invention Since the compound of the present invention exhibits stable smectic A phase and smectic C phase, it is useful when producing a liquid crystal material that utilizes smectic A phase or smectic C phase. In particular, when creating a liquid crystal composition for use in a ferroelectric liquid crystal display device in combination with another liquid crystal compound exhibiting a smectic C phase, the compound of the present invention causes a smectic A phase to appear on top of the smectic C phase, resulting in INAC, IAC
It is useful for creating liquid crystal compositions having a phase series such as.
第１図〜第３図は、それぞれこの発明の実施例１、実施
例３．実施例４でえられたフルオロアルキル系化合物の
赤外吸収スペクトルの図である。1 to 3 show Example 1 and Example 3 of the present invention, respectively. FIG. 3 is a diagram of an infrared absorption spectrum of a fluoroalkyl compound obtained in Example 4.
Claims (1)
式、化学式、表等があります▼又は▲数式、化学式、表
等があります▼又は▲数式、化学式、表等があります▼
、 ｍは１又は２、ｎは１〜１５の整数を示す）で表わされ
るフルオロアルキル系化合物。 ２、前記式（ I ）で表わされるフルオロアルキル系化
合物の少なくとも１種を含有してなる液晶組成物。[Claims] 1. General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ... (I) (However, R is an alkyl group having 1 to 15 carbon atoms, A is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼or▲There are mathematical formulas, chemical formulas, tables, etc.▼or▲There are mathematical formulas, chemical formulas, tables, etc.▼
, m is 1 or 2, n is an integer of 1 to 15). 2. A liquid crystal composition containing at least one fluoroalkyl compound represented by the above formula (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22083588A JPH0269443A (en) | 1988-09-02 | 1988-09-02 | Fluoroalkyl based compound and liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22083588A JPH0269443A (en) | 1988-09-02 | 1988-09-02 | Fluoroalkyl based compound and liquid crystal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0269443A true JPH0269443A (en) | 1990-03-08 |
| JPH0588696B2 JPH0588696B2 (en) | 1993-12-24 |
Family
ID=16757289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22083588A Granted JPH0269443A (en) | 1988-09-02 | 1988-09-02 | Fluoroalkyl based compound and liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0269443A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142753A (en) * | 1988-09-23 | 1990-05-31 | Minnesota Mining & Mfg Co <3M> | Achiral fluorine-containing liquid crystal |
| US5580488A (en) * | 1993-05-17 | 1996-12-03 | Canon Kabushiki Kaisha | Mesomorphic compound liquid crystal composition containing the compound, liquid crystal device using the composition, display apparatus and display method |
| US5593616A (en) * | 1993-09-17 | 1997-01-14 | Canon Kabushiki Kaisha | Optically inactive, mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5658491A (en) * | 1995-10-12 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5688437A (en) * | 1994-04-14 | 1997-11-18 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5855812A (en) * | 1997-04-11 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Compounds and process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US6309561B1 (en) | 1997-12-24 | 2001-10-30 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US7973194B1 (en) | 2010-03-18 | 2011-07-05 | Eastman Chemical Company | High solvating cyclohexane dicarboxylate diesters plasticizers |
| JP2011231098A (en) * | 2009-12-01 | 2011-11-17 | Sumitomo Chemical Co Ltd | Production method of cycloalkanedicarboxylic acid monoesters |
-
1988
- 1988-09-02 JP JP22083588A patent/JPH0269443A/en active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142753A (en) * | 1988-09-23 | 1990-05-31 | Minnesota Mining & Mfg Co <3M> | Achiral fluorine-containing liquid crystal |
| US5580488A (en) * | 1993-05-17 | 1996-12-03 | Canon Kabushiki Kaisha | Mesomorphic compound liquid crystal composition containing the compound, liquid crystal device using the composition, display apparatus and display method |
| US5593616A (en) * | 1993-09-17 | 1997-01-14 | Canon Kabushiki Kaisha | Optically inactive, mesomorphic compound, liquid crystal composition containing the compound, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5688437A (en) * | 1994-04-14 | 1997-11-18 | Canon Kabushiki Kaisha | Liquid crystal composition, liquid crystal device using the composition, liquid crystal apparatus and display method |
| US5702637A (en) * | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5972241A (en) * | 1995-04-19 | 1999-10-26 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5658491A (en) * | 1995-10-12 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5928562A (en) * | 1995-10-12 | 1999-07-27 | Minnesota Mining And Manufacturing Company | Process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US5855812A (en) * | 1997-04-11 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Compounds and process for controlling cone tilt angle in mixtures of smectic liquid crystal compounds |
| US6309561B1 (en) | 1997-12-24 | 2001-10-30 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| JP2011231098A (en) * | 2009-12-01 | 2011-11-17 | Sumitomo Chemical Co Ltd | Production method of cycloalkanedicarboxylic acid monoesters |
| US7973194B1 (en) | 2010-03-18 | 2011-07-05 | Eastman Chemical Company | High solvating cyclohexane dicarboxylate diesters plasticizers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0588696B2 (en) | 1993-12-24 |
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