JP2000256228A - Alkenylcyclobutane compound - Google Patents
Alkenylcyclobutane compoundInfo
- Publication number
- JP2000256228A JP2000256228A JP11059345A JP5934599A JP2000256228A JP 2000256228 A JP2000256228 A JP 2000256228A JP 11059345 A JP11059345 A JP 11059345A JP 5934599 A JP5934599 A JP 5934599A JP 2000256228 A JP2000256228 A JP 2000256228A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- liquid crystal
- iodide
- formula
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 40
- 239000000203 mixture Substances 0.000 abstract description 31
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 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 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000012071 phase Substances 0.000 description 25
- -1 isooctyl Chemical group 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 230000007704 transition Effects 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 230000018199 S phase Effects 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- DXVOSTCYXXRQEW-UHFFFAOYSA-N iodocyclobutane Chemical compound IC1CCC1 DXVOSTCYXXRQEW-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
- LNEMDIUSUQPKIP-UHFFFAOYSA-N 2-phenyl-1,3-dioxane Chemical compound O1CCCOC1C1=CC=CC=C1 LNEMDIUSUQPKIP-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OFAKCHSSNAJPAJ-HFFNAHSWSA-N CCCCC[C@H](CC1)CC[C@@H]1C(CC1)CCC1C=O Chemical compound CCCCC[C@H](CC1)CC[C@@H]1C(CC1)CCC1C=O OFAKCHSSNAJPAJ-HFFNAHSWSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 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
- 239000012769 display material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 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
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- 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 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- MYXJYAIKMQJHIB-UHFFFAOYSA-M sodium;benzenesulfinate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)C1=CC=CC=C1 MYXJYAIKMQJHIB-UHFFFAOYSA-M 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、電気光学的表示材
料として新規なアルケニルシクロブタン化合物に関し、
詳しくは、液晶組成物の粘度を大きく増加させることな
く高いＮＩ点を与える新規なアルケニルシクロブタン化
合物に関するものである。The present invention relates to a novel alkenylcyclobutane compound as an electro-optical display material,
More specifically, the present invention relates to a novel alkenylcyclobutane compound that provides a high NI point without greatly increasing the viscosity of a liquid crystal composition.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】液晶の
電気光学的効果を利用した液晶表示素子の普及により、
これらの用途に適した特性を有する液晶化合物が求めら
れている。液晶表示素子に用いられる液晶化合物に要求
される特性としては次に示す（１）〜（５）等がある。2. Description of the Related Art With the spread of liquid crystal display devices utilizing the electro-optical effect of liquid crystal,
There is a need for liquid crystal compounds having properties suitable for these uses. Characteristics required for a liquid crystal compound used in a liquid crystal display element include the following (1) to (5).
【０００３】（１）液晶の物理的、化学的安定性が大き
いこと。 （２）室温を含む広い温度範囲で液晶相を示すこと。 （３）広い温度範囲で応答性がよいこと。 （４）駆動回路との整合性がよいこと。 （５）光学的異方性が光学的要請にかなった値であるこ
と。(1) The physical and chemical stability of the liquid crystal is large. (2) exhibiting a liquid crystal phase in a wide temperature range including room temperature. (3) Good responsiveness over a wide temperature range. (4) Good matching with the drive circuit. (5) Optical anisotropy is a value meeting optical requirements.
【０００４】このような特性を全て満足する単一の液晶
化合物は現在のところ知られておらず、数種類の液晶化
合物を混合した液晶組成物として上記の諸物性を満足さ
せようとしているのが現状である。[0004] A single liquid crystal compound satisfying all of these characteristics is not known at present, and it is presently intended to satisfy the above-mentioned various properties as a liquid crystal composition obtained by mixing several kinds of liquid crystal compounds. It is.
【０００５】液晶組成物は、その温度により、低温側か
ら結晶相（以下、「Ｃ相」と記述する）、場合によって
スメクチック相（以下、「Ｓ相」と記述する）を経由し
てネマチック相（以下、「Ｎ相」と記述する）となり、
さらに高温で等方性液体相（以下、「Ｉ相」と記述す
る）となる。このうち、Ｓ相とＮ相が液晶相であり、液
晶の性質を示す。液晶化合物を含有する液晶組成物は室
温を含む広い温度範囲で液晶相であることが必要であ
り、この液晶温度範囲が広いことは、広範な使用環境に
おいて良好な表示が得られることを意味するものであ
る。よって、Ｃ相からＮ相へ相転移する温度（ＣＮ点）
が低く、Ｎ相からＩ相へ相転移する温度（ＮＩ点）の高
いものが好ましい。特に、高温となる使用環境で使用さ
れる場合には、ＮＩ点の高い液晶組成物が必要となる。
このため、ネマチック液晶材料に混合し、ＮＩ点を上げ
る効果を与える化合物が求められてきた。[0005] Depending on the temperature of the liquid crystal composition, a nematic phase via a crystalline phase (hereinafter referred to as "C phase") and a smectic phase (hereinafter referred to as "S phase") depending on the temperature. (Hereinafter referred to as "N-phase").
At an even higher temperature, it becomes an isotropic liquid phase (hereinafter, referred to as “I phase”). Among them, the S phase and the N phase are liquid crystal phases, and exhibit properties of liquid crystal. A liquid crystal composition containing a liquid crystal compound needs to be in a liquid crystal phase in a wide temperature range including room temperature, and a wide liquid crystal temperature range means that good display can be obtained in a wide use environment. Things. Therefore, the temperature at which the phase transitions from C phase to N phase (CN point)
And a temperature at which the phase transition from the N phase to the I phase (NI point) is high is preferable. In particular, when used in a high-temperature use environment, a liquid crystal composition having a high NI point is required.
Therefore, there has been a demand for a compound which is mixed with a nematic liquid crystal material and has an effect of increasing the NI point.
【０００６】また、液晶相での粘度は、応答性に影響を
与える。粘度が高いと液晶化合物の分子の動きが遅くな
り応答速度が低下するので、液晶化合物は、混合した場
合に液晶組成物の粘度を増加させないことが重要であ
り、粘度を低減させることが好ましい。[0006] The viscosity in the liquid crystal phase affects the responsiveness. When the viscosity is high, the movement of the molecules of the liquid crystal compound is slowed and the response speed is reduced. Therefore, it is important that the liquid crystal compound does not increase the viscosity of the liquid crystal composition when mixed, and it is preferable to reduce the viscosity.
【０００７】例えば、特開昭６２−２０１８４３号公
報、特開平２−８５２１８号公報、特開平２−８５２１
９号公報及び特表平７−５０６１１７には、それぞれア
ルキルシクロブタン化合物の使用が提案されているが、
上記要求に対し満足のいく性能を与えるものではなかっ
た。For example, Japanese Patent Application Laid-Open Nos. 62-201843, 2-85218, 2-8521
No. 9 and Japanese Translation of PCT International Publication No. 7-506117 propose the use of alkylcyclobutane compounds, respectively.
It did not give satisfactory performance to the above requirements.
【０００８】従って、本発明の目的は、液晶組成物に添
加されて、該液晶組成物の粘度を増加させることなく、
高温域を含む広い温度範囲での液晶相を与えることので
きる新規な化合物を提供することにある。Accordingly, it is an object of the present invention to provide a liquid crystal composition which is added to a liquid crystal composition without increasing the viscosity of the liquid crystal composition.
It is an object of the present invention to provide a novel compound capable of providing a liquid crystal phase in a wide temperature range including a high temperature range.
【０００９】[0009]
【課題を解決するための手段】本発明者らは、鋭意検討
を重ねた結果、新規な特定のアルケニルシクロブタン化
合物が、上記目的を達成し得ることを知見した。Means for Solving the Problems As a result of intensive studies, the present inventors have found that a novel specific alkenylcyclobutane compound can achieve the above object.
【００１０】本発明は、上記知見に基づきなされたもの
で、下記〔化２〕（前記〔化１〕と同じ）の一般式
（Ｉ）で表される新規なアルケニルシクロブタン化合物
を提供するものである。The present invention has been made based on the above findings, and provides a novel alkenylcyclobutane compound represented by the following general formula (I) of the following [formula 2] (same as the above [formula 1]). is there.
【００１１】[0011]
【化２】 Embedded image
【００１２】[0012]
【発明の実施の形態】以下、本発明のアルケニルシクロ
ブタン化合物について詳述する。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the alkenylcyclobutane compound of the present invention will be described in detail.
【００１３】本発明の化合物は、新規な化合物であり、
上記一般式（Ｉ）で表されるアルケニルシクロブタン化
合物である。上記一般式（Ｉ）中のＲ及びｂで表される
フッ素原子で置換されていてもよい炭素数１〜１０のア
ルキル基としては、メチル、トリフルオロメチル、ペン
タフルオロエチル、プロピル、イソプロピル、ブチル、
イソブチル、ペンチル、ヘキシル、ヘプチル、オクチ
ル、イソオクチル、ノニル、デシル等が挙げられ、ｂで
表されるフッ素原子で置換されていてもよいアルコキシ
基は上記アルキル基から誘導される基が挙げられ、ａ、
ｂ及びｃで表されるハロゲン原子としては、Ｆ、Ｃｌ、
Ｂｒ、Ｉが挙げられる。The compound of the present invention is a novel compound,
An alkenylcyclobutane compound represented by the general formula (I). Examples of the alkyl group having 1 to 10 carbon atoms which may be substituted by a fluorine atom represented by R and b in the above general formula (I) include methyl, trifluoromethyl, pentafluoroethyl, propyl, isopropyl and butyl ,
Isobutyl, pentyl, hexyl, heptyl, octyl, isooctyl, nonyl, decyl and the like, and the alkoxy group optionally substituted by a fluorine atom represented by b includes a group derived from the above alkyl group, ,
As the halogen atom represented by b and c, F, Cl,
Br and I.
【００１４】本発明のアルケニルシクロブタン化合物の
例としては、特に制限を受けないが、好ましい具体例と
して、下記〔化３〕〜〔化９〕に記載の化合物Ｎｏ．１
〜Ｎｏ．７等が挙げられる。Examples of the alkenylcyclobutane compound of the present invention are not particularly limited, but preferred specific examples are compound Nos. 1
-No. 7 and the like.
【００１５】[0015]
【化３】 Embedded image
【００１６】[0016]
【化４】 Embedded image
【００１７】[0017]
【化５】 Embedded image
【００１８】[0018]
【化６】 Embedded image
【００１９】[0019]
【化７】 Embedded image
【００２０】[0020]
【化８】 Embedded image
【００２１】[0021]
【化９】 Embedded image
【００２２】本発明のアルケニルシクロブタン化合物
は、液晶組成物に添加されて使用される。該液晶組成物
として使用される液晶化合物は、特に制限されることは
ないが、ビフェニル系、エステル系、アゾキシ系、シク
ロヘキサンカルボン酸フェニルエステル系、フェニルシ
クロヘキサン系、フェニルピリミジン系、フェニルメタ
ジオキサン系、シアノビフェニル系、シアノターフェニ
ル系、シアノビフェニルシクロヘキサン系、トラン系、
エタン系等が挙げられ、これらは一種又は二種以上で使
用される。The alkenylcyclobutane compound of the present invention is used by being added to a liquid crystal composition. The liquid crystal compound used as the liquid crystal composition is not particularly limited, but biphenyl, ester, azoxy, cyclohexanecarboxylic acid phenyl ester, phenylcyclohexane, phenylpyrimidine, phenylmetadioxane, Cyanobiphenyl, cyanoterphenyl, cyanobiphenylcyclohexane, tolan,
Ethane and the like are used, and these are used alone or in combination of two or more.
【００２３】上記の液晶化合物は、例えば、下記一般式
〔化１０〕で表される化合物のように例示することがで
きる。The above liquid crystal compound can be exemplified, for example, as a compound represented by the following general formula [Formula 10].
【００２４】[0024]
【化１０】 Embedded image
【００２５】上記一般式〔化１０〕で表される化合物の
具体例としては、下記〔化１１〕の各化合物等が挙げら
れる。尚、各化合物におけるＹ1 、Ｙ2 、Ｙ3 及びＹ
は、上記一般式〔化１０〕におけるものと同じ意味であ
る。Specific examples of the compound represented by the above general formula [Chemical Formula 10] include the following compounds of the following [Chemical Formula 11]. Incidentally, Y 1 , Y 2 , Y 3 and Y
Has the same meaning as in the above general formula [Formula 10].
【００２６】[0026]
【化１１】 Embedded image
【００２７】本発明のアルケニルシクロブタン化合物の
液晶組成物に対する添加量は、該液晶組成物１００重量
部に対して、好ましくは０．１〜１００重量部、更に好
ましくは１〜５０重量部である。The amount of the alkenylcyclobutane compound of the present invention to be added to the liquid crystal composition is preferably 0.1 to 100 parts by weight, more preferably 1 to 50 parts by weight, based on 100 parts by weight of the liquid crystal composition.
【００２８】本発明のアルケニルシクロブタン化合物
は、その製造方法によって制限されることはないが、該
当するシクロブチルアルコールから誘導することができ
る。例えば、該アルコールをヨウ素化しアルキルシクロ
ブチルアイオダイドを合成し、これを四級塩化して得ら
れたアルキルシクロブチル化合物の四級塩と、必要な構
造を有するアルデヒドとを反応させることでアルケニル
シクロブタン化合物のシス−トランス体が得られる。そ
の後、トランス体を分離することで目的の化合物を得る
ことができる。The alkenylcyclobutane compound of the present invention is not limited by the production method, but can be derived from the corresponding cyclobutyl alcohol. For example, alkenylcyclobutane is obtained by reacting a quaternary salt of an alkylcyclobutyl compound obtained by iodination of the alcohol to produce an alkylcyclobutyl iodide, and quaternary salification thereof, with an aldehyde having a required structure. A cis-trans form of the compound is obtained. Then, the desired compound can be obtained by separating the trans form.
【００２９】[0029]
【実施例】以下、実施例、評価例をもって本発明を更に
詳細に説明する。しかしながら、本発明は以下の実施
例、評価例によって制限を受けるものではない。The present invention will be described below in more detail with reference to examples and evaluation examples. However, the present invention is not limited by the following examples and evaluation examples.
【００３０】（実施例１）化合物Ｎｏ．１の製造 シクロブチルアイオダイドの合成 ５００ｍｌフラスコにシクロブチルメタノール１０．１
６ｇ（０．１１８ｍｏｌ）、イミダゾール１２．００ｇ
（０．１７７ｍｏｌ）、トリフェニルフォスフィン４
６．２６ｇ（０．１７７ｍｏｌ）、トルエン５０ｇを仕
込み、撹拌混合してからヨウ素４４．９２ｇ（０．１７
７ｍｏｌ）を加えた。１時間室温撹拌した後、チオ硫酸
ナトリウム水溶液、蒸留水の順で反応系を洗浄し、ロー
タリエバポレーターで濃縮を行い、得られた濃縮物を、
ヘキサン溶媒、シリカゲルカラムで分離精製を行い、シ
クロブチルアイオダイド１８．５ｇを得た（収率：８０
％）。Example 1 Compound No. Preparation of 1 Synthesis of cyclobutyl iodide Cyclobutyl methanol 10.1 in a 500 ml flask
6 g (0.118 mol), 12.00 g of imidazole
(0.177 mol), triphenylphosphine 4
6.26 g (0.177 mol) and 50 g of toluene were charged and mixed by stirring, and then 44.92 g (0.17 mol) of iodine.
7 mol). After stirring at room temperature for 1 hour, the reaction system was washed with an aqueous solution of sodium thiosulfate and distilled water, and concentrated with a rotary evaporator.
Separation and purification were performed using a hexane solvent and a silica gel column to obtain 18.5 g of cyclobutyl iodide (yield: 80).
%).
【００３１】シクロブチルメチルトリフェニルフォス
フォニウムアイオダイドの合成 アルゴン置換した５００ｍｌフラスコに上記アイオダイ
ド１５．００ｇ（０．０７６５ｍｏｌ）、トリフェニル
フォスフィン２０．０ｇ（０．０７６５ｍｏｌ）、ジメ
チルホルムアミド２０ｍｌを仕込み、アルゴン気流下で
１２０℃で３時間加熱撹拌した後、トルエン１４０ｍｌ
を加え、１０℃に冷却した。析出した結晶を濾取、減圧
下８０℃で乾燥し目的化合物を２４．２４ｇ得た（収
率：７０％）。Synthesis of cyclobutylmethyltriphenylphosphonium iodide In a 500 ml flask purged with argon, 15.00 g (0.0765 mol) of the above iodide, 20.0 g (0.0765 mol) of triphenylphosphine, and 20 ml of dimethylformamide were charged. After heating and stirring at 120 ° C. for 3 hours under an argon stream, toluene 140 ml
And cooled to 10 ° C. The precipitated crystals were collected by filtration and dried at 80 ° C. under reduced pressure to obtain 24.24 g of the desired compound (yield: 70%).
【００３２】化合物Ｎｏ．１（シス−トランス混合
物）の合成 アルゴン置換した１００ｍｌフラスコに上記で得たシ
クロブチルメチルトリフェニルフォスフォニウムアイオ
ダイド１５．００ｇ（０．０３２７ｍｏｌ）、ｔ−ブチ
ルメチルエーテル４０ｍｌを仕込み、懸濁させた後、２
０℃で２，２−ジメチルエトキシカリウム３．９２ｇ
（０．０３５０ｍｏｌ）を加え、室温で１時間撹拌し
た。これを０℃に冷却し、４−（トランス−４−ペンチ
ルシクロヘキシル）シクロヘキサンカルボアルデヒド
５．７７ｇ（０．０２１８ｍｏｌ）をｔ−ブチルメチル
エーテル４０ｍｌに溶かした溶液を反応系の温度を０℃
に保持したまま２０分で滴下し、室温で１時間撹拌し
た。得られた反応液を蒸留水４０ｇで洗浄後、硫酸マグ
ネシウムで乾燥後、溶媒を留去し、ヘキサン溶媒、シリ
カゲルカラムで精製し、目的の化合物とシス体の混合物
を３．３８ｇ得た（収率：４９％）。Compound No. Synthesis of 1 (cis-trans mixture) In a 100 ml flask purged with argon, 15.00 g (0.0327 mol) of cyclobutylmethyltriphenylphosphonium iodide obtained above and 40 ml of t-butylmethylether were charged and suspended. After 2
3.92 g of potassium 2,2-dimethylethoxy at 0 ° C.
(0.0350 mol), and the mixture was stirred at room temperature for 1 hour. This was cooled to 0 ° C., and a solution of 5.77 g (0.0218 mol) of 4- (trans-4-pentylcyclohexyl) cyclohexanecarbaldehyde dissolved in 40 ml of t-butyl methyl ether was heated to 0 ° C.
, And the mixture was stirred at room temperature for 1 hour. The obtained reaction solution was washed with 40 g of distilled water, dried over magnesium sulfate, the solvent was distilled off, and the residue was purified with a hexane solvent and a silica gel column to obtain 3.38 g of a mixture of the desired compound and the cis-isomer. Rate: 49%).
【００３３】異性化処理（トランス体分離） アルゴン置換した５００ｍｌフラスコに上記で得られ
たシス−トランス混合物全量とベンゼンスルフィン酸ナ
トリウム２水和物０．７０ｇ、３Ｎ塩酸１．１７ｇ、ト
ルエン７５ｍｌを仕込み、アルゴン気流下、６５℃で２
時間加熱撹拌した。冷却後、反応液を３回水洗し、硫酸
マグネシウムで乾燥、溶媒を除去し、ヘキサン溶媒、シ
リカゲルカラムで精製した後、更に酢酸エチル−エタノ
ール溶媒から再結晶を２回行い目的の化合物Ｎｏ．１を
１．１５ｇ得た（収率３４％）。Isomerization (Trans Isolation) A 500 ml flask purged with argon is charged with the total amount of the cis-trans mixture obtained above, 0.70 g of sodium benzenesulfinate dihydrate, 1.17 g of 3N hydrochloric acid and 75 ml of toluene. At 65 ° C under an argon stream
The mixture was heated and stirred for an hour. After cooling, the reaction solution was washed with water three times, dried over magnesium sulfate, the solvent was removed, and the residue was purified with a hexane solvent and a silica gel column. 1.15 g of Compound 1 was obtained (yield 34%).
【００３４】キャラクタリゼーション、物性測定 上記で得た化合物について、キャラクタリゼーション
を行い、目的の化合物Ｎｏ．１であることを確認し、相
転移温度を測定した。結果を以下に示す。1Ｈ−ＮＭＲ
分析結果 ０．６−２．２ｐｐｍ（多重ピーク：３８Ｈ） ２．６−３．０ｐｐｍ（多重ピーク： ２Ｈ） ５．１−５．７ｐｐｍ（多重ピーク： ２Ｈ） ＩＲ分析結果（単位：ｃｍ-1） ２９５０、２９１０、２８５０、１４６０、１４４０、
９６０、９００相転移温度測定 融点：１２４℃Characterization and Measurement of Physical Properties The compound obtained above was characterized and the desired compound No. After confirming that it was 1, the phase transition temperature was measured. The results are shown below. 1 H-NMR
Analysis result 0.6-2.2 ppm (multiple peak: 38H) 2.6-3.0 ppm (multiple peak: 2H) 5.1-5.7 ppm (multiple peak: 2H) IR analysis result (unit: cm -1) ) 2950, 2910, 2850, 1460, 1440,
960, 900 phase transition temperature measurement Melting point: 124 ° C
【００３５】（実施例２）化合物Ｎｏ．２の製造上記実
施例１と同様のスケール、操作手順で合成を行った。 ３−ブチルシクロブチルアイオダイドの合成 ３−ブチルシクロブチルメタノール１６．７８ｇから３
−ブチルシクロブチルアイオダイド２４．１０ｇを得た
（収率：８１％）。 ３−ブチルシクロブチルメチルトリフェニルフォスフ
ォニウムアイオダイドの合成 ３−ブチルシクロブチルアイオダイド１９．２９ｇから
３−ブチルシクロブチルメチルトリフェニルフォスフォ
ニウムアイオダイドを１９．６８ｇ得た（収率：５０
％）。Example 2 Compound no. Production of 2 Synthesis was performed in the same scale and operating procedure as in Example 1 above. Synthesis of 3-butylcyclobutyl iodide 3-butylcyclobutylmethanol from 16.78 g to 3
24.10 g of -butylcyclobutyl iodide was obtained (yield: 81%). Synthesis of 3-butylcyclobutylmethyltriphenylphosphonium iodide 19.68 g of 3-butylcyclobutylmethyltriphenylphosphonium iodide was obtained from 19.29 g of 3-butylcyclobutyliodide (yield: 50).
%).
【００３６】化合物Ｎｏ．２の合成（シス−トランス
混合物） ３−ブチルシクロブチルメチルトリフェニルフォスフォ
ニウムアイオダイド１６．８２ｇと（３，４−ジフルオ
ロフェニル）−４−（トランス−４−シクロヘキシル）
−トランス−４−シクロヘキサンカルボアルデヒド６．
６５ｇから目的の化合物とシス体の混合物を４．６８ｇ
得た（収率：６０％）。 異性化処理（トランス体分離） 上記で得られた結晶３．８２ｇから目的の化合物Ｎｏ．
２を０．３４ｇ得た（収率：９％）。Compound No. Synthesis of 2 (cis-trans mixture) 16.82 g of 3-butylcyclobutylmethyltriphenylphosphonium iodide and (3,4-difluorophenyl) -4- (trans-4-cyclohexyl)
-Trans-4-cyclohexanecarbaldehyde6.
4.68 g of a mixture of the desired compound and the cis form from 65 g
Obtained (yield: 60%). Isomerization treatment (trans-isolation) From 3.82 g of the crystals obtained above, the target compound No.
0.34 g of Compound 2 was obtained (yield: 9%).
【００３７】キャラクタリゼーション、物性測定 上記で得た化合物について下記の方法でキャラクタリ
ゼーションを行い、目的の化合物Ｎｏ．２であることを
確認し、相転移温度を測定した。結果を以下に示す。1 Ｈ−ＮＭＲ分析結果 ０．８−３．０ｐｐｍ（多重ピーク：３５Ｈ） ５．２−５．６ｐｐｍ（多重ピーク： ２Ｈ） ６．８−７．２ｐｐｍ（多重ピーク： ３Ｈ） ＩＲ分析結果（単位：ｃｍ-1） ２９５０、２９１０、２８５０、１６００、１５１０、
１４４０、１４３０、１２８０、１２７０、１２００、
１１１０、９６０、８１０、７７０相転移温度測定 ＣＮ点５７℃、ＮＩ点１３９℃Characterization and Measurement of Physical Properties The compound obtained above was characterized by the following method, and the target compound No. 2 and the phase transition temperature was measured. The results are shown below. 1 H-NMR analysis result 0.8-3.0 ppm (multiple peak: 35H) 5.2-5.6 ppm (multiple peak: 2H) 6.8-7.2 ppm (multiple peak: 3H) IR analysis result (unit) : Cm -1 ) 2950, 2910, 2850, 1600, 1510,
1440, 1430, 1280, 270, 1200,
1110, 960, 810, 770 phase transition temperature measurement CN point 57 ° C, NI point 139 ° C
【００３８】（実施例３）化合物Ｎｏ．３の製造 上記実施例１と同様のスケール、操作手順で合成を行っ
た。 シクロブチルアイオダイドの合成 実施例１に記載した。 シクロブチルメチルトリフェニルフォスフォニウムア
イオダイドの合成 実施例１に記載した。Example 3 Compound no. Manufacture of 3 Synthesis was performed by the same scale and operating procedure as in Example 1 above. Synthesis of cyclobutyl iodide As described in Example 1. Synthesis of cyclobutylmethyltriphenylphosphonium iodide As described in Example 1.
【００３９】化合物Ｎｏ．３の合成（シス−トランス
混合物） シクロブチルメチルトリフェニルフォスフォニウムアイ
オダイド１５．００ｇと（４−シアノフェニル）−４−
（トランス−４−シクロヘキシル）−トランス−４−シ
クロヘキサンカルボアルデヒド６．４４ｇから目的の化
合物とシス体の混合物を９．９１ｇ得た（収率：９９
％）。 異性化処理（トランス体分離） 上記で得られた結晶４．９１ｇから目的の化合物Ｎｏ．
３を０．７４ｇ得た（収率：１５％）。Compound No. Synthesis of 3 (cis-trans mixture) 15.00 g of cyclobutylmethyltriphenylphosphonium iodide and (4-cyanophenyl) -4-
From 9.44 g of (trans-4-cyclohexyl) -trans-4-cyclohexanecarbaldehyde, 9.91 g of a mixture of a target compound and a cis-isomer was obtained (yield: 99).
%). Isomerization treatment (trans isomer separation) From 4.91 g of the crystals obtained above, the target compound No.
0.74 g of Compound No. 3 was obtained (yield: 15%).
【００４０】物性特性、キャラクタリゼーション 上記で得た化合物について下記の方法でキャラクタリ
ゼーションを行い、目的の化合物Ｎｏ．３であることを
確認し、相転移温度を測定した。結果を以下に示す。1 Ｈ−ＮＭＲ分析結果 ０．８−３．０ｐｐｍ（多重ピーク：２７Ｈ） ５．１−５．７ｐｐｍ（多重ピーク： ２Ｈ） ７．２−７．７ｐｐｍ（多重ピーク： ４Ｈ） ＩＲ分析結果（単位：ｃｍ-1） ２９７０、２９４０、２８６０、２２４０、１６１０、
１５１０、１４５０、９７０、８６０、８４０、５７０
相転移温度 ＣＮ点：１１６℃、ＮＩ点２５８℃Physical properties and characterization The compound obtained above was characterized by the following method to obtain the desired compound No. 3, and the phase transition temperature was measured. The results are shown below. 1 H-NMR analysis result 0.8-3.0 ppm (multiple peak: 27H) 5.1-5.7 ppm (multiple peak: 2H) 7.2-7.7 ppm (multiple peak: 4H) IR analysis result (unit) : Cm -1 ) 2970, 2940, 2860, 2240, 1610,
1510, 1450, 970, 860, 840, 570
Phase transition temperature CN point: 116 ° C, NI point 258 ° C
【００４１】（評価例）上記実施例によって得られた化
合物Ｎｏ．１及びＮｏ．２それぞれ１重量部と下記〔化
１２〕に示す配合の液晶組成物９重量部とを混合して、
２種の液晶組成物Ａ及びＢとし、それぞれの各種物性を
測定した。それらの結果を表１に示す。(Evaluation Example) Compound No. 1 obtained in the above example was used. 1 and No. 1 2 1 part by weight of each and 9 parts by weight of a liquid crystal composition having the composition shown in the following [Chemical Formula 12] were mixed,
Two kinds of liquid crystal compositions A and B were used, and various physical properties were measured. Table 1 shows the results.
【００４２】[0042]
【化１２】 Embedded image
【００４３】[0043]
【表１】 [Table 1]
【００４４】上記結果から、外挿方により求めた化合物
Ｎｏ．１及びＮｏ．２の物性を表２に表す。From the above results, Compound No. 1 and No. 1 Table 2 shows the physical properties of Sample No. 2.
【００４５】[0045]
【表２】 [Table 2]
【００４６】また、化合物Ｎｏ．１について外挿法によ
りＮＩ点を求めた結果、５７℃であった。Compound No. As a result of obtaining an NI point of the sample No. 1 by an extrapolation method, it was 57 ° C.
【００４７】以上の結果より、本発明の新規なアルケニ
ルシクロブチル化合物を使用すれば、低粘度で、高いＮ
Ｉ点を持つ液晶組成物が得られることが判る。From the above results, using the novel alkenylcyclobutyl compound of the present invention, low viscosity and high N
It can be seen that a liquid crystal composition having point I is obtained.
【００４８】[0048]
【発明の効果】本発明のアルケニルシクロブチル化合物
は、液晶組成物に添加されて、該液晶組成物の粘度を増
加させることなく、高温域を含む広い温度範囲での液晶
相を与えることのできるものである。The alkenylcyclobutyl compound of the present invention can be added to a liquid crystal composition to give a liquid crystal phase in a wide temperature range including a high temperature range without increasing the viscosity of the liquid crystal composition. Things.
Claims (1)
アルケニルシクロブタン化合物。 【化１】 An alkenylcyclobutane compound represented by the following general formula (I): Embedded image
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242855A (en) * | 2013-05-15 | 2013-08-14 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclobutyl and difluorometheneoxy |
| CN103275735A (en) * | 2013-05-13 | 2013-09-04 | 石家庄诚志永华显示材料有限公司 | Dielectric positive liquid crystal composition |
| CN103305231A (en) * | 2013-06-13 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composite containing difluorooxymethylene bridge polar monomer compound |
| CN103305229A (en) * | 2013-06-06 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition capable of rapidly responding to cyclo-butylbenzene difluoromethoxy |
-
1999
- 1999-03-05 JP JP11059345A patent/JP2000256228A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103275735A (en) * | 2013-05-13 | 2013-09-04 | 石家庄诚志永华显示材料有限公司 | Dielectric positive liquid crystal composition |
| CN103242855A (en) * | 2013-05-15 | 2013-08-14 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclobutyl and difluorometheneoxy |
| CN103242855B (en) * | 2013-05-15 | 2015-06-17 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclobutyl and difluorometheneoxy |
| CN103305229A (en) * | 2013-06-06 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition capable of rapidly responding to cyclo-butylbenzene difluoromethoxy |
| CN103305229B (en) * | 2013-06-06 | 2015-09-02 | 石家庄诚志永华显示材料有限公司 | A kind of ring butylbenzene difluoromethoxy class fast response liquid crystal composition |
| CN103305231A (en) * | 2013-06-13 | 2013-09-18 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composite containing difluorooxymethylene bridge polar monomer compound |
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