JP2812398B2 - Novel ether compound and liquid crystal composition containing the same - Google Patents
Novel ether compound and liquid crystal composition containing the sameInfo
- Publication number
- JP2812398B2 JP2812398B2 JP2000234A JP23490A JP2812398B2 JP 2812398 B2 JP2812398 B2 JP 2812398B2 JP 2000234 A JP2000234 A JP 2000234A JP 23490 A JP23490 A JP 23490A JP 2812398 B2 JP2812398 B2 JP 2812398B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- phase
- ether compound
- crystal composition
- pyrimidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 8
- -1 ether compound Chemical class 0.000 title description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000004990 Smectic liquid crystal Substances 0.000 description 12
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 8
- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000010287 polarization Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SEGJDCGIQJESDC-UHFFFAOYSA-N 2-methylbutyl 3-phenylprop-2-enoate Chemical compound CCC(C)COC(=O)C=CC1=CC=CC=C1 SEGJDCGIQJESDC-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000819 phase cycle Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance 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)
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
ターヘッド、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エーテル化合物及びこの化合物を
含む液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial application field) The present invention can take a stable thermotropic liquid crystal state, for example, for a display such as a liquid crystal television, an optical printer head, an optical Fourier transform element, a light valve, etc. The present invention relates to a novel ether compound used as a liquid crystal material useful as a material for optoelectronics-related devices, and a liquid crystal composition containing the 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（ΔεE2/2）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10m
secと遅い。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。(Prior Art) At present, liquid crystal materials are used as various display elements such as watches, calculators, small televisions, etc., and these are mainly nematic liquid crystal materials. The nematic liquid crystal, for utilizing operating based on weak interactions between the dielectric anisotropy Δε and the electric field E (ΔεE 2/2), the number response time to electric field 10m
sec and slow. For this reason, the use in a field where a high-speed response is required is limited, and the display capacity is reaching its limit, which is one of the obstacles in achieving a large screen.
ところで、1975年、R.B.Meyerらによって合成された
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（DOBAMBC）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（SSFLC）セルにより、μ sec
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, the appearance of ferroelectric liquid crystal represented by 4- (4-n-decyloxybenzylideneamino) cinnamic acid-2-methylbutyl ester (DOBAMBC) synthesized by RBMeyer et al. NAClark used
The surface-stabilized ferroelectric liquid crystal (SSFLC) cell utilizing the bistable state in thin cells proposed by
A liquid crystal cell with high-speed response and memory performance on the order has been made possible.
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 and proposed to date.
（発明が解決しようとする課題） ところで、これまで合成、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
リミ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）。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
電性液晶組成物を与えることができないのが現状であ
る。(Problems to be Solved by the Invention) By the way, in order for a ferroelectric liquid crystal compound synthesized and proposed to be used as a liquid crystal material, it exhibits a chiral smectic C phase at least in a wide temperature range near room temperature and exhibits a large spontaneous It must be polarized and 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, there has been a move to address this by mixing several types of compounds. there were. Incidentally, as this kind of liquid crystal material, a kind of phenylpyrimidine compound has been proposed (for example, JP-A-63-235393). However, at present, there are few kinds of such ferroelectric liquid crystal compounds, and it is impossible to provide a sufficiently 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チックＣ相を示し、大きな
自発分極を有する液晶組成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。Accordingly, an object of the present invention is to provide a novel ether compound which is chemically stable, exhibits a chiral smectic C phase in a wide temperature range near room temperature, and is useful as a material for a liquid crystal composition having a large spontaneous polarization. is there.
（課題を解決するための手段） 本発明は次の一般式、 （式中、R1およびR2は炭素数１〜18のアルキル基で、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およびこの化合
物を含有する液晶組成物からなるものである。(Means for Solving the Problems) The present invention provides the following general formula: Wherein R 1 and R 2 are alkyl groups having 1 to 18 carbon atoms, which may be the same or different, and C * represents an asymmetric carbon. It comprises a liquid crystal composition.
本発明の上記式の化合物におけるR1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。R 1 and R 2 in the compounds of the above formula of the present invention are selected from alkyl groups having 1 to 18 carbon atoms from a practical manufacturing point of view.
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 its physicochemical properties are as follows.
５−（４−（１−フルオロメチルヘプチルオキシ）フェ
ニル）−２−（４−ブチルオキシフェニル）ピリミジン IR（KBr,cm-1）:2920,2850,1605,1580,1510,1430,1250,
1165,820,7901 H−NMR（CDCl3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,2H）,4.
6（dd,J＝45Hz,5,2H）,4.7〜4.2（1H）,4.1（t,2H）,2.
0〜1.1（14H）,1.0（t,6H） Mass（M+）:450 ５−（４−（１−フルオロメチルヘプチルオキシ）フェ
ニル２−（４−ヘキシルオキシフェニル）ピリミジン IR（KBr,cm-1）:2920,2850,1605,1580,1510,1435,1250,
1165,825,7951 H−NMR（CDCl3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,2H）,4.
6（dd,J＝45Hz,5,2H）,4.7〜4.2（1H）,41（t,2H）,2.0
〜1.1（18H）,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
方法で合成することができる。5- (4- (1-fluoromethylheptyloxy) phenyl) -2- (4-butyloxyphenyl) pyrimidine IR (KBr, cm -1 ): 2920,2850,1605,1580,1510,1430,1250,
1165,820,790 1 H-NMR (in CDCl 3 , TMS standard, δ value ppm): 8.9 (s, 2H),
8.4 (d, 2H), 7.5 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 4.
6 (dd, J = 45Hz, 5.2H), 4.7-4.2 (1H), 4.1 (t, 2H), 2.
0-1.1 (14H), 1.0 (t, 6H) Mass (M + ): 450 5- (4- (1-fluoromethylheptyloxy) phenyl 2- (4-hexyloxyphenyl) pyrimidine IR (KBr, cm -1 ): 2920,2850,1605,1580,1510,1435,1250,
1165,825,795 1 H-NMR (in CDCl 3 , TMS standard, δ value ppm): 8.9 (s, 2H),
8.4 (d, 2H), 7.5 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 4.
6 (dd, J = 45Hz, 5.2H), 4.7-4.2 (1H), 41 (t, 2H), 2.0
1.1 (18H), 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、ピリジンの存在下、光学活性な１−フルオロ−
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）ピリミジン
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）ピリミジンを得ることができる。First, in the presence of pyridine, optically active 1-fluoro-
The 2-alkanol is reacted with trifluoromethylsulfonic anhydride to obtain 1-fluoromethylalkyl triflate. Next, this is reacted with 2- (4-alkyloxyphenyl) -5- (4-hydroxyphenyl) pyrimidine and a phenoxide anion generated from sodium hydroxide, whereby an ether compound represented by the above general formula, 5- (4- (1-Fluoromethylalkyloxy) phenyl) -2- (4-alkyloxyphenyl) pyrimidine can be obtained.
なお、光学活性な１−フルオロ−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ミン
フッ化水素錯体を作用させることにより合成することが
できる（日本化学会第58春季年会1989.4 4 III I 2
8）。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）ピリミジンは、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
ルフュア プラクティーセ ヘミー（Journal fuer Pra
ktische Chemie）323巻、２号、199〜206頁（1981）に
記載の方法に準じて合成することができる。The optically active 1-fluoro-2-alkanol can be synthesized by reacting a commercially available optically active 1,2-epoxyalkane with an amine hydrogen fluoride complex (The 58th Annual Meeting of the Chemical Society of Japan, Apr. 1989. 4 III I 2
8). Also, 2- (4-alkyloxyphenyl) -5
-(4-Hydroxyphenyl) pyrimidine is obtained by starting from 4-alkyloxycyanobenzene as a starting material in Journal fuer Praise
ktische 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 can also be used as a mixture with another liquid crystal material. For example, when mixed with a pyrimidine-based liquid crystal material, the phase sequence of the base liquid crystal is not changed and the chiral smectic C phase can be changed from the smectic A phase.
It has very good effects such as increasing the transition temperature to the phase, 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。(Examples) Next, the present invention will be specifically described with reference to examples.
実施例１ ５−（４−（１−フルオロメチルヘプチルオキシ）フェ
ニル）−２−（４−ブチルオキシフェニル）ピリミジン （１）１−フルオロメチルヘプチルトリフレートの合成 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（16.5mmol）を、蒸留したジクロロメタン4mlに溶
解させ、５℃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（15mmol）と
ピリジン1.19g（15mmol）、ジクロロメタン4mlとの混合
物を５℃以下で50分かけて滴下し、そのまま１時間撹拌
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7mlを加えて１−
フルオロメチルヘプチルトリフレートの1mmol/ml溶液を
調製した。Example 1 5- (4- (1-fluoromethylheptyloxy) phenyl) -2- (4-butyloxyphenyl) pyrimidine (1) Synthesis of 1-fluoromethylheptyl triflate Under a nitrogen atmosphere, trifluoromethanesulfonic anhydride Stuff
4.65 g (16.5 mmol) was dissolved in 4 ml of distilled dichloromethane and cooled to 5 ° C. or lower. In addition, (R)-( - )
A mixture of 2.22 g (15 mmol) of -1-fluoro-2-octanol, 1.19 g (15 mmol) of pyridine, and 4 ml of dichloromethane was added dropwise at 5 ° C. or lower over 50 minutes, and stirring was continued for 1 hour. The obtained reaction product was passed through a filter tube filled with sodium sulfate to remove salts, and 7 ml of dichloromethane was added to add 1-mL.
A 1 mmol / ml solution of fluoromethylheptyl triflate was prepared.
（２）最終目的化合物の合成 ジクロロメタン25ml中に２−（４−ブチルオキシフェ
ニル）−５−（４−ヒドロキシフェニル）ピリミジン0.
96g（3mmol）と水酸化ナトリウム0.3gを混合し、10分間
撹拌した後、これに、先に調製した１−フルオロメチル
ヘプチルトリフレートの1mmol/ml−CH2Cl2溶液3ml（3mm
ol）を添加した。次いで、室温で45時間撹拌した後、希
塩酸中に反応液を注ぎ、酸性でクロロホルム抽出した。(2) Synthesis of final target compound 2- (4-butyloxyphenyl) -5- (4-hydroxyphenyl) pyrimidine in 25 ml of dichloromethane.
After mixing 96 g (3 mmol) and 0.3 g of sodium hydroxide and stirring for 10 minutes, 3 ml of a 1 mmol / ml-CH 2 Cl 2 solution of 1-fluoromethylheptyl triflate prepared above (3 mm
ol) was added. Next, after stirring at room temperature for 45 hours, the reaction solution was poured into dilute hydrochloric acid, and extracted with chloroform under acidic conditions.
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−フルオロメチルフペチルオキシ）フェニ
ル）−２−（４−ブチルオキシフェニル）ピリミジン0.
35g（収率26％）を得た。After distilling off the solvent, the residue was purified by silica gel chromatography and recrystallized to give 5-
(4- (1-fluoromethylfutyloxy) phenyl) -2- (4-butyloxyphenyl) pyrimidine
35 g (26% yield) were obtained.
（３）液晶性の評価 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℃の割合で行
た。(3) Evaluation of Liquid Crystallinity The above compound was injected into a 2.7 μm-thick cell made of glass with a transparent electrode coated with polyimide and subjected to rubbing treatment, and observed with a polarizing microscope while controlling the temperature with a hot stage. Was. The temperature was changed at a rate of 2 ° C. per minute.
この結果、降温過程では、75.1℃で等方性液体からコ
レステリック相に、また72.7℃でキラルスメクチックＣ
相となり、40℃で結晶になった。As a result, during the cooling process, the isotropic liquid changed to a cholesteric phase at 75.1 ° C and chiral smectic C at 72.7 ° C.
It became a phase and became crystalline at 40 ° C.
また、自発分極を三角波法で測定したところ、67.7
℃、10Vpp/μm,100Hzの条件で140nC/cm2を、また47.7℃
で205nC/cm2を示した。When the spontaneous polarization was measured by the triangular wave method,
140nC / cm 2 under the conditions of 10 ℃, 10Vpp / μm, 100Hz, and 47.7 ℃
Showed 205 nC / cm 2 .
一方、75〜66℃でネマチック相を、66〜54℃でスメク
チックＡ相を、また54〜−３℃でスメクチックＣ相をと
る非キラルのピリミジン系ベース液晶に、上記で合成し
た５−（４−（１−フルオロメチルヘプチルオキシフェ
ニル）−２−（４−ブチルオキシフェニル）ピリミジン
を18％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℃でコレステリック相を、66〜60℃
でスメクチックＡ相を、また60〜−16℃でキラルスメク
チックＣ相をとり、25℃での自発分極が10.3nC/cm2、傾
き角が24.9゜、応答時間が52μ secを示した。On the other hand, the non-chiral pyrimidine-based liquid crystal having 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 in 5- (4). When 18% of-(1-fluoromethylheptyloxyphenyl) -2- (4-butyloxyphenyl) pyrimidine was added and the liquid crystallinity was evaluated in the same cell as above, the cholesteric phase was found to be at 75 to 66 ° C. , 66-60 ℃
And a chiral smectic C phase at 60 to -16 ° C, a spontaneous polarization at 25 ° C of 10.3 nC / cm 2 , an inclination angle of 24.9 ° and a response time of 52 µsec.
実施例２ ５−（４−（１−フルオロメチルヘプチルオキシ）フェ
ニル）−２−（４−ヘキシルオキシ）フェニル）ピリミ
ジン （１）最終目的化合物の合成 実施例１で使用した２−（４−ブチルオキシフェニ
ル）−５−（４−ヒドロキシフェニル）ピリミジン0.96
gの代わりに２−（４−ヘキシルオキシフェニル）−５
−（４−ヒドロキシフェニル）ピリミジン1.04g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
ロメチルヘプチルオキシ）フェニル）−２−（４−ヘキ
シルオキシフェニル）ピリミジン0.32g（収率22％）を
得た。Example 2 5- (4- (1-fluoromethylheptyloxy) phenyl) -2- (4-hexyloxy) phenyl) pyrimidine (1) Synthesis of final target compound 2- (4-butyl) used in Example 1 (Oxyphenyl) -5- (4-hydroxyphenyl) pyrimidine 0.96
2- (4-hexyloxyphenyl) -5 instead of g
Except that 1.04 g of-(4-hydroxyphenyl) pyrimidine was used, in the same manner as described in Example 1,
0.32 g (yield 22%) of 5- (4- (1-fluoromethylheptyloxy) phenyl) -2- (4-hexyloxyphenyl) pyrimidine having the above-mentioned physicochemical properties was obtained.
（２）液晶性の評価 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℃で等方性液体から一瞬コレステリ
ック相を生じた後、キラルスメクチックＣ相になった。(2) Evaluation of Liquid Crystallinity Evaluation was performed in the same manner as described in Example 1. As a result, a cholesteric phase was instantaneously generated from the isotropic liquid at 81 ° C. in the course of the temperature drop, and then became a chiral smectic C phase.
また、自発分極を三角波法で測定したところ、69℃,1
0Vpp/μm,100Hzの条件で125nC/cm2を示した。The spontaneous polarization was measured by the triangular wave method.
It showed 125 nC / cm 2 under the conditions of 0 Vpp / μm and 100 Hz.
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、更にはベ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, the compounds of the present invention show a chiral smectic C phase over a wide temperature range, show a large spontaneous polarization, and further, when mixed with a base liquid crystal material, change the phase series of the base liquid crystal. Increase the transition temperature from the smectic A phase to the chiral smectic C phase,
It can be seen that it has the effect of 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 described above, the novel ether compound of the present invention is chemically stable, turns into a ferroelectric liquid crystal by itself, and has good properties when mixed with other liquid crystal compounds. It exerts an extraordinary effect such as imparting, and can be used as a liquid crystal material useful for optoelectronics-related elements.
フロントページの続き (72)発明者 平井 利弘 埼玉県戸田市新曽南３丁目17番35号 日 本鉱業株式会社内 (58)調査した分野(Int.Cl.6，ＤＢ名) C07D 239/26 C09K 19/34 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ) ＷＰＩＤＳ（ＳＴＮ)Continuation of the front page (72) Inventor Toshihiro Hirai 3-17-35 Niisominami, Toda City, Saitama Japan Co., Ltd. (58) Field surveyed (Int. Cl. 6 , DB name) C07D 239/26 C09K 19/34 CA (STN) REGISTRY (STN) WPIDS (STN)
Claims (2)
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。(1) a general formula, (Wherein, R 1 and R 2 are alkyl groups having 1 to 18 carbon atoms, which may be the same or different, and C * represents an asymmetric carbon).
成物。2. A liquid crystal composition containing the compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000234A 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 |
|---|---|---|---|
| JP2000234A 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 JPH03206081A (en) | 1991-09-09 |
| JP2812398B2 true JP2812398B2 (en) | 1998-10-22 |
Family
ID=11468278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000234A 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 JP2000234A patent/JP2812398B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03206081A (en) | 1991-09-09 |
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