JPH03206081A - New ether compound and liquid crystal composition containing same compound - Google Patents
New ether compound and liquid crystal composition containing same compoundInfo
- Publication number
- JPH03206081A JPH03206081A JP23490A JP23490A JPH03206081A JP H03206081 A JPH03206081 A JP H03206081A JP 23490 A JP23490 A JP 23490A JP 23490 A JP23490 A JP 23490A JP H03206081 A JPH03206081 A JP H03206081A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- pyrimidine
- crystal composition
- composition containing
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 20
- -1 ether compound Chemical class 0.000 title claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 9
- 239000000203 mixture Substances 0.000 title claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000010287 polarization Effects 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- DBLQYFAVEZPBCD-UHFFFAOYSA-N C1=CC(OC(CF)CCCCCC)=CC=C1C1=CN=C(C=2C=CC(OCCCC)=CC=2)N=C1 Chemical compound C1=CC(OC(CF)CCCCCC)=CC=C1C1=CN=C(C=2C=CC(OCCCC)=CC=2)N=C1 DBLQYFAVEZPBCD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PHMRQMJVXACJHA-UHFFFAOYSA-N 2-(4-hexoxyphenyl)pyrimidine Chemical compound C1=CC(OCCCCCC)=CC=C1C1=NC=CC=N1 PHMRQMJVXACJHA-UHFFFAOYSA-N 0.000 description 1
- UTIMESSLYFMSPO-UHFFFAOYSA-N 2-methylbutyl 3-[4-[(4-decoxyphenyl)methylideneamino]phenyl]prop-2-enoate Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C=NC1=CC=C(C=CC(=O)OCC(C)CC)C=C1 UTIMESSLYFMSPO-UHFFFAOYSA-N 0.000 description 1
- CNDUVHIFNJWFPD-UHFFFAOYSA-N 4-[2-(4-butoxyphenyl)pyrimidin-5-yl]phenol Chemical compound C1=CC(OCCCC)=CC=C1C1=NC=C(C=2C=CC(O)=CC=2)C=N1 CNDUVHIFNJWFPD-UHFFFAOYSA-N 0.000 description 1
- ATMZRGCMFDOUNX-UHFFFAOYSA-N 4-[6-(4-hexoxyphenyl)pyridin-3-yl]phenol Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=N1 ATMZRGCMFDOUNX-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007334 memory performance Effects 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
Landscapes
- 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、安定なサーモトロピックな液晶状態をとり得
、例えば、液晶テレビ等のディスプレイ用、光プリンタ
ーヘンド、光フーリエ変換素子、ライトバルブ等のオプ
トエレクトロニクス関連素子の素材として有用な液晶材
料に利用される新規工−テル化合物及びこの化合物を含
む液晶組底物に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention can take a stable thermotropic liquid crystal state, and can be used, for example, in displays such as liquid crystal televisions, optical printer heads, optical Fourier transform elements, and light valves. The present invention relates to a novel ether compound used as a liquid crystal material useful as a material for optoelectronics-related elements such as, and a liquid crystal composite containing this compound.
（従来の技術）
現在、時計、電卓、小型テレビ等、種々の表示素子とし
て液晶材料が用いられているが、これらは、主にネマチ
ック液晶材料である。このネマチック液晶は、誘電異方
性Δεと電場Ｅとの弱い相互作用（ΔεＥ”／２）に基
づく作動を利用するため、電場に対する応答時間が数１
０ｍ ｓｅｃと遅い。(Prior Art) Currently, liquid crystal materials are used as various display elements for watches, calculators, small televisions, etc., but these are mainly nematic liquid crystal materials. This nematic liquid crystal utilizes operation based on the weak interaction between dielectric anisotropy Δε and electric field E (ΔεE”/2), so the response time to electric field is several orders of magnitude.
It is slow at 0 msec.
このため、高速応答が要求される分野での利用には制限
があり、また、表示容量の点でも限界に達しつつあり、
大画面化を図る上での障害の一つになっている。For this reason, there are limits to its use in fields that require high-speed response, and the display capacity is also reaching its limit.
This is one of the obstacles to achieving larger screens.
ところで、１９７５年、Ｒ．Ｂ．Ｍｅｙｅｒらによって
合威された４−（４−ｎ−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（ＤＯＢＡ
ＭＢＣ）を代表例とする強誘電性液晶の出現と、それを
用いたＮ．Ａ．Ｃｌａｒｋらの提案による薄いセルにお
ける双安定状態を利用する表面安定化強誘電性液晶（Ｓ
ＳＦＬＣ）セルにより、μｓｅｃオーダーの高速応答性
及びメモリー性を有する液晶セルが可能となった。By the way, in 1975, R. B. 4-(4-n-decyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (DOBA), which was developed by Meyer et al.
The emergence of ferroelectric liquid crystals, with MBC as a representative example, and N. A. Surface-stabilized ferroelectric liquid crystal (S) utilizing bistable states in thin cells proposed by Clark et al.
SFLC) cells have made possible liquid crystal cells with high-speed response on the μsec order and memory performance.
このため、現在まで多くの強誘電性液晶化合物が合成、
提案されている。For this reason, many ferroelectric liquid crystal compounds have been synthesized to date.
Proposed.
（発明が解決しようとする課題）
ところで、これまで合戒、提案された強誘電性液晶化合
物が液晶材料として用いられるためには、少なくとも室
温近傍の広い温度範囲でキラルスメクチックＣ相を示し
、大きな自発分極を有し、化学的に安定なものであるこ
とが必要である。しかし、単一の化合物で、これらの要
求を満足するものを得ることは困難であり、従来のネマ
チック液晶材料の場合と同様に、これまでは数種類の化
合物を混合することにより対処しようという動きにあっ
た。ちなみに、この種の液晶材料として、フェニルピリ
ξジン化合物の一種が提案されている（例えば、特開昭
６３−２３５３９３号公報）。(Problem to be Solved by the Invention) By the way, in order for the ferroelectric liquid crystal compounds that have been proposed so far to be used as liquid crystal materials, they must exhibit a chiral smectic C phase in a wide temperature range at least near room temperature, and have a large It needs to have spontaneous polarization and be chemically stable. However, it is difficult to obtain a single compound that satisfies these requirements, and, as in the case of conventional nematic liquid crystal materials, efforts have been made to address this by mixing several types of compounds. there were. Incidentally, a type of phenylpyridine ξdine compound has been proposed as this type of liquid crystal material (for example, Japanese Patent Application Laid-Open No. 63-235393).
しかし、かかる強誘電性液晶化合物は、未だその種類も
少なく、充分に満足できる強誘電性液晶組或物を与える
ことができないのが現状である。However, there are still only a few types of such ferroelectric liquid crystal compounds, and it is currently impossible to provide a fully satisfactory ferroelectric liquid crystal composition.
そこで、本発明の目的は、化学的に安定で、室温近傍の
広い温度範囲でキラルスメクチノクＣ相を示し、大きな
自発分極を有する液晶組戒物の材料として有用な新規エ
ーテル化合物を提供することにある。Therefore, an object of the present invention is to provide a novel ether compound that is chemically stable, exhibits a chiral smectinol C phase in a wide temperature range near room temperature, and has a large spontaneous polarization, and is useful as a material for liquid crystal compounds. There is a particular thing.
（課題を解決するための手段）
本発明は次の一般式、
（式中、ＲｌおよびＲ２は炭素数１〜１８のアルキル基
で、同しものでも異なっているものでもよく、Ｃ“は不
斉炭素を示す）で表される新規エーテル化合物およびこ
の化合物を含有する液晶組戒物からなるものである。(Means for Solving the Problems) The present invention has the following general formula: It consists of a new ether compound represented by (indicating the same carbon) and a liquid crystal composition containing this compound.
本発明の上記式の化合物におけるＲｌおよびＲ２は、実
用的な製造上の見地から炭素数１〜１８のアルキル基か
ら選定される。Rl and R2 in the compound of the above formula of the present invention are selected from alkyl groups having 1 to 18 carbon atoms from the viewpoint of practical production.
この化合物の代表的な例とその理化学的性質を示すと次
の通りである。Representative examples of this compound and their physical and chemical properties are as follows.
−２− （４−プチルオキシフエニル）ビＩミジンｒＲ
（ＫＢｒ， ｃｍ−’） ： ２９２０， ２８５
０， １６０５， １５８０． １５１０，１，
４３０， １２５０， １１６５， ８２０．
７９０’Ｈ−ＮＭＲ （ＣＤＣＩ．ｓ中、ＴＭＳ基準
、δ値ｐｐｍ） ：８．９（ｓ， ２｝１） ，
８．４（ｄ， ２Ｈ）， ７．５（ｄ． ２Ｈ
）， ７．１（ｄ， ２Ｈ）， ７．０（ｄ， ２Ｈ
）， ４．６（ｄｄ， Ｊ＝４５Ｈｚ． ５． ２８）
，４．７〜４．２（ＩＨ）， ４．Ｈｔ， ２Ｈ），
２．０〜１．１ （１４８） ，１．０（ｔ．６Ｈ
）
Ｍａｓｓ（Ｍ” ）： ４５０
２−（４−へキシルオキシフエニル）ビリミジンＩＲ（
ＫＢｒ， ｃｍ−’） ： ２９２０， ２８
５０， １６０５， １５８０， １５１０１４
３５，１２５０，１１６５，８２５，７９５Ｈ−ＮＭＲ
（ＣＤＣ１３中、ＴＭＳ基準、δ値ｐｐｍ） ：８．９
（ｓ， ２Ｈ）． ８．４（ｄ， ２Ｈ）． ７．５（
ｄ， ２Ｈ）， ７．１（ｄ， ２Ｈ）， ７．０
（ｄ， ２｝ＩＬ ４．６（ｄｄ， Ｊ＝４５Ｈ
ｚ， ５， ２Ｈ），４．７〜４．２（ＩＨ），
４１（ｔ． ２Ｂ）， ２．０〜１．Ｈ１８｝１
），０．９（ｔ． ６Ｈ）
Ｍａｓｓ（Ｍ” ）： ４７８
上記一般式で示される本発明のエーテル化合物は次の方
法で合戒することができる。-2- (4-butyloxyphenyl) bimidine rR
(KBr, cm-'): 2920, 285
0, 1605, 1580. 1510,1,
430, 1250, 1165, 820.
790'H-NMR (in CDCI.s, TMS standard, δ value ppm): 8.9 (s, 2}1),
8.4 (d, 2H), 7.5 (d. 2H
), 7.1(d, 2H), 7.0(d, 2H
), 4.6 (dd, J=45Hz. 5.28)
, 4.7-4.2 (IH), 4. Ht, 2H),
2.0~1.1 (148), 1.0 (t.6H
) Mass (M”): 450 2-(4-hexyloxyphenyl)pyrimidine IR(
KBr, cm-'): 2920, 28
50, 1605, 1580, 151014
35,1250,1165,825,795H-NMR
(CDC13, TMS standard, δ value ppm): 8.9
(s, 2H). 8.4(d, 2H). 7.5 (
d, 2H), 7.1(d, 2H), 7.0
(d, 2}IL 4.6 (dd, J=45H
z, 5, 2H), 4.7-4.2 (IH),
41 (t. 2B), 2.0-1. H18}1
), 0.9 (t. 6H) Mass (M''): 478 The ether compound of the present invention represented by the above general formula can be synthesized by the following method.
先ず、ビリジンの存在下、光学活性なｌ−フルオ口−２
〜アルカノールとトリフルオロメチルスルホン酸無水物
を反応させて、１−フルオロメチルアルキルトリフレー
トを得る。次に、これを２＝（４−アルキルオキシフェ
ニル） −５− （４ヒドロキシフェニル）ビリミジン
と水酸化ナトリウムから発生させたフェノキシドアニオ
ンと反応させ、これにより上記一般式で示されるエーテ
ル化合物、すなわち５− （４− （１−フルオロメチ
ルアルキルオキシ）フェニル）−２− （４−アルキル
オキシフェニル）ビリミジンを得ることができる。First, in the presence of pyridine, optically active l-fluoro-2
-Reacting an alkanol with trifluoromethylsulfonic anhydride to obtain 1-fluoromethylalkyl triflate. Next, this is reacted with a phenoxide anion generated from 2=(4-alkyloxyphenyl)-5-(4hydroxyphenyl)pyrimidine and sodium hydroxide, thereby producing an ether compound represented by the above general formula, i.e., 5 - (4-(1-fluoromethylalkyloxy)phenyl)-2-(4-alkyloxyphenyl)pyrimidine can be obtained.
なお、光学活性な１−フルオ口−２−アルカノールは、
市販の光学活性な１，２−エポキシアルカンにアごンフ
ッ化水素錯体を作用させることにより合戒することがで
きる（日本化学会第５８春季年会１９８９．４ ４Ｉ
［［１２８）。また、２−（４アルキルオキシフェニル
）−５− （４−ヒドロキシフェニル）ビリミジンは、
４−アルキルオキシシアノベンゼンを出発原料として、
ジャーナルフユア ベラクティーセ ヘミー（Ｊｏｕｒ
ｎａｌ ｆｕｅｒＰｒａｋｔｉｓｃｈｅ Ｃｈｅｍｉｅ
） ３２３巻、２号、１９９〜２０６頁（１９８１）に
記載の方法に準して合威することができる。In addition, the optically active 1-fluoro-2-alkanol is
It can be cured by reacting a commercially available optically active 1,2-epoxyalkane with an agone hydrogen fluoride complex (Chemical Society of Japan 58th Spring Annual Meeting 1989.4 4I)
[[128). In addition, 2-(4alkyloxyphenyl)-5-(4-hydroxyphenyl)pyrimidine is
Using 4-alkyloxycyanobenzene as a starting material,
Journal
nal fuelPraktische Chemie
) Vol. 323, No. 2, pp. 199-206 (1981).
本発明のエーテル化合物は、単独でも強誘電性液晶材料
として利用することができるが、他の液晶材料と混合し
て用いることもできる。例えば、ピリミジン系の液晶材
料と混合すると、このベース液晶の相系列を変えること
なく、かつスメクチックＡ相からキラルスメクチックＣ
相への転移温度を上昇させ、応答速度を高め、また傾き
角を大きくする等、極めて良好な作用をなす。The ether compound of the present invention can be used alone as a ferroelectric liquid crystal material, but it can also be used in combination with other liquid crystal materials. For example, when mixed with a pyrimidine-based liquid crystal material, the phase sequence of the base liquid crystal can be changed from smectic A to chiral smectic C without changing the phase series of the base liquid crystal.
It has extremely good effects, such as increasing the phase transition temperature, increasing the response speed, and increasing the tilt angle.
（実施例） 次に、本発明を実施例により具体的に説明する。(Example) Next, the present invention will be specifically explained using examples.
実施置土
５− （４− （１−フルオロメチルへプチルオキシ）
フェニル）−２−（４−プチルオキシフェニル）ビリミ
ジン窒素雰囲気下、トリフルオロメタンスルホン酸無水
物４．６５ｇ （１６．５ ｍｍｏｌ）を、蒸留したジ
クｏｏメタン４ ｍＲに溶解させ、５゜Ｃ以下に冷却し
た。これに、（Ｒ） −（−） −１−フルオロ−２−
オクタノール２．２２ｇ（１５ ｍｍｏｌ）とビリジン
１．１９ｇ （１５ｍｍｏｌ）ジクロロメタン４ｄとの
混合物を５゜Ｃ以下で５０分かけて滴下し、そのまま１
時間攪拌し続けた。得られた反応物を、芒硝を詰めた濾
過管に通し、塩を除去した後、ジクロロメタン７ｄを加
えて１フルオロメチルへプチルトリフレートのｌ ｍｍ
ｏｌ／一溶液を調製した。Implementation soil 5- (4- (1-fluoromethylheptyloxy)
Phenyl)-2-(4-butyloxyphenyl)pyrimidine Under a nitrogen atmosphere, 4.65 g (16.5 mmol) of trifluoromethanesulfonic anhydride was dissolved in 4 mR of distilled dimethane, and the mixture was heated to below 5°C. Cooled. To this, (R) -(-) -1-fluoro-2-
A mixture of 2.22 g (15 mmol) of octanol, 1.19 g (15 mmol) of pyridine, and 4 d of dichloromethane was added dropwise at a temperature below 5°C over a period of 50 minutes.
Continue stirring for hours. The obtained reaction product was passed through a filtration tube filled with Glauber's salt to remove salt, and 7 d of dichloromethane was added to obtain 1 mm of 1 fluoromethyl heptyl triflate.
An ol/1 solution was prepared.
ｆｆｉ）ＪＪ’．百一約−仕，金東ぽと１戊ジクロ口メ
タン２５ｍＲ中に２−（４−プチルオキシフェニル）−
５− （４−ヒドロキシフェニル）ビリミジン０．９６
ｇ （ ３ ｍｍｏｌ ）と水酸化ナトリウム０．３
ｇを混合し、１０分間攪拌した後、これに、先に二周
製した１−フノレオ口メチノレヘフ゜チノレトリフレー
トの１ ｍｍｏｌ ／ ｍＱ ＣｔｈＣｌｚ溶液３ｍ
ｌ（３ｍｍｏｌ）を添加した。次いで、室温で４５時間
攪拌した後、希塩酸中に反応液を注ぎ、酸性でクロロホ
ルム抽出した。ffi) JJ'. 101 Approximately - 2-(4-butyloxyphenyl)- in 25 mR of dichloromethane
5-(4-hydroxyphenyl)pyrimidine 0.96
g (3 mmol) and sodium hydroxide 0.3
After stirring for 10 minutes, to this was added 3 ml of a 1 mmol/mQ CthClz solution of 1-fluoromethylene triflate prepared twice previously.
1 (3 mmol) was added. After stirring at room temperature for 45 hours, the reaction solution was poured into diluted hydrochloric acid and extracted with acidic chloroform.
溶媒を留去後、シリカゲルクロマトグラフィーで精製し
、再結晶して、前述した理化学的性質を有する５− （
４− （１−フルオロメチルへプチルオキシ）フェニル
）−２− （４−プチルオキシフェニル）ピリミジン０
．３５ｇ （収率２６％）を得た。After distilling off the solvent, it is purified by silica gel chromatography and recrystallized to obtain 5-(
4-(1-fluoromethylheptyloxy)phenyl)-2-(4-butyloxyphenyl)pyrimidine 0
．． 35 g (yield 26%) was obtained.
紐戒益二坐葺鳳
上記化合物を、ポリイミドを塗布しラビング処理を施し
た透明電極付ガラスからなる厚さ２．７μｍのセルに注
入し、ホットステージで温度制御を行いながら、偏光顕
微鏡観察を行った。温度変化は１分間に２゜Ｃの割合で
行った。The above compound was injected into a 2.7 μm thick cell made of glass with transparent electrodes coated with polyimide and rubbed, and observed with a polarized light microscope while controlling the temperature on a hot stage. went. The temperature was changed at a rate of 2°C per minute.
この結果、降温過程では、７５．１゜Ｃで等方性液体か
らコレステリンク相に、また７２．７゜Ｃでキラルスメ
クチックＣ相となり、４０゜Ｃで結晶になった。As a result, during the cooling process, it changed from an isotropic liquid to a cholesteric phase at 75.1°C, changed to a chiral smectic C phase at 72.7°C, and became a crystal at 40°C.
また、自発分極を三角波法で測定したところ、６７．７
゜Ｃ、１０ Ｖｐｐ／ ａｍ． １００ Ｈｚの条件て
１４０ｎＣ／ｃｍ２を、また４７，７゜Ｃで２０５ ｎ
Ｃ／ｃｍ２を示した。In addition, when the spontaneous polarization was measured using the triangular wave method, it was found to be 67.7.
°C, 10 Vpp/am. 140 nC/cm2 at 100 Hz and 205 nC at 47.7°C
C/cm2.
一方、７５〜６６゜Ｃでネマチノク相を、６６〜５４゜
ＣでスメクチックＡ相を、また５４〜−３゜Ｃでスメク
チンクＣ相をとる非キラルのビリミシン系ベース液晶に
、上記で合威した５− （４− （１−フルオロメチル
へプチルオキシフェニル） −２− （４ブチルオキシ
フェニル）ピリミジンをｌ８％添加し、上記と同様のセ
ルで液晶性の評価を行なったところ、７５〜６６゜Ｃで
コレステリック相を、６６〜６０’ＣでスメクチックＡ
相を、また６０〜−１６゜ＣでキラルスメクチックＣ相
をとり、２５゜Ｃでの自発分極が１０．３ｎＣ／ｃｍ”
、傾き角が２４．９゜、応答時間が５２μｓｅｃを示し
た。On the other hand, the non-chiral birimycin-based liquid crystal which takes a nematic phase at 75 to 66°C, a smectic A phase at 66 to 54°C, and a smectic C phase at 54 to -3°C was synthesized as described above. When 8% of 5-(4-(1-fluoromethylheptyloxyphenyl)-2-(4butyloxyphenyl)pyrimidine was added) and the liquid crystallinity was evaluated in the same cell as above, the result was 75-66°. C for cholesteric phase, 66-60'C for smectic A
It also takes a chiral smectic C phase at 60 to -16°C, and has a spontaneous polarization of 10.3 nC/cm at 25°C.
, the tilt angle was 24.9°, and the response time was 52 μsec.
実１０艷え
５− （４− （１−フルオロメチルへプチルオキシ）
フェニル）−２−（４−へキシルオキシ）フェニル）ビ
リミジン実施例１で使用した２−（４−プチルオキシフ
ェニル）−５− （４−ヒドロキシフェニル）ビリミジ
ン０．９６ ｇの代わりに２−（４−へキシルオキシフ
エニル）−５− （４−ヒドロキシフェニル）ビリ稟ジ
ン１．０４ ｇを用いた以外は全て、実施例１に記載の
方法と同様の方法で、前述した理化学的性質を有する５
− （４− （１−フルオロメチルへプチルオキシ）フ
ェニル）−１− （４−へキシルオキシフェニル〉ビリ
くジン０．３２ ｇ （収率２２％）を得た。Fruit 10 5- (4- (1-fluoromethylheptyloxy)
phenyl)-2-(4-hexyloxy)phenyl)pyrimidine Instead of 0.96 g of 2-(4-butyloxyphenyl)-5-(4-hydroxyphenyl)pyrimidine used in Example 1, 2-(4 -hexyloxyphenyl)-5-(4-hydroxyphenyl)pyridine, which has the above-mentioned physicochemical properties, was prepared in the same manner as described in Example 1, except that 1.04 g of pyridine was used. 5
-(4-(1-Fluoromethylheptyloxy)phenyl)-1-(4-hexyloxyphenyl) 0.32 g (yield 22%) of biridine was obtained.
辺櫃益丘魚磐債
実施例１に記載した方法と同様にして評価したところ、
降温過程で、８１”Ｃで等方性液体から一瞬コレステリ
ック相を生した後、キラルスメクチックＣ相になった。When evaluated in the same manner as described in Example 1 of the Bento Yoshioka Uoiwa Bond,
During the cooling process, a cholesteric phase was generated momentarily from an isotropic liquid at 81''C, and then a chiral smectic C phase was formed.
また、自発分極を三角波法で測定したところ、６９゜Ｃ
，１０νｐｐ／ ａｍ ， １００ Ｈｚの条件で１２
５ ｎＣ／ｃｍ”を示した。In addition, when spontaneous polarization was measured using the triangular wave method, it was found to be 69°C.
, 10νpp/am, 12 under the conditions of 100 Hz
5 nC/cm".
以上の実施例の結果から、本発明の化合物は広い温度範
囲でキラルスメクチックＣ相を示し、また大きな自発分
極を示し、更にはヘース液晶材料と混合した場合にはベ
ース液晶の相系列を変えることなくスメクチックＡ相か
らキラルスメクチックＣ相への転移温度を上昇させ、応
答速度を高め、また傾き角をより大きくする作用を有す
ることがわかる。From the results of the above examples, it is clear that the compound of the present invention exhibits a chiral smectic C phase over a wide temperature range, exhibits large spontaneous polarization, and also changes the phase series of the base liquid crystal when mixed with a Haes liquid crystal material. It can be seen that it has the effect of increasing the transition temperature from the smectic A phase to the chiral smectic C phase, increasing the response speed, and increasing the tilt angle.
（発明の効果）
以上説明してきたように、本発明の新規エーテル化合物
は、化学的に安定で、それ自体で強誘電性液晶となり、
また他の液晶化合物と混合することにより、良好な性質
を付与する等の格別の効果を奏し、オプトエレクトロニ
クス関連素子に有用な液晶材料として利用できる。(Effects of the Invention) As explained above, the novel ether compound of the present invention is chemically stable, becomes a ferroelectric liquid crystal by itself,
In addition, by mixing it with other liquid crystal compounds, it exhibits special effects such as imparting good properties, and can be used as a liquid crystal material useful for optoelectronic-related elements.
Claims (1)
ル基で、同じものでも異なっているものでもよく、Ｃ＾
＊は不斉炭素を示す）で表される新規エーテル化合物。 ２、請求項１に記載の化合物を含有する液晶組成物。[Claims] 1. General formula, ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^1 and R^2 are alkyl groups having 1 to 18 carbon atoms, and may be the same or different. But it's okay, C^
A new ether compound represented by *indicates an asymmetric carbon. 2. A liquid crystal composition containing the compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23490A JP2812398B2 (en) | 1990-01-06 | 1990-01-06 | Novel ether compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23490A JP2812398B2 (en) | 1990-01-06 | 1990-01-06 | Novel ether compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03206081A true JPH03206081A (en) | 1991-09-09 |
| JP2812398B2 JP2812398B2 (en) | 1998-10-22 |
Family
ID=11468278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP23490A Expired - Lifetime JP2812398B2 (en) | 1990-01-06 | 1990-01-06 | Novel ether compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2812398B2 (en) |
-
1990
- 1990-01-06 JP JP23490A patent/JP2812398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2812398B2 (en) | 1998-10-22 |
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