JPS62286943A - 4'-substituted biphenyl crotyl ether derivative - Google Patents
4'-substituted biphenyl crotyl ether derivativeInfo
- Publication number
- JPS62286943A JPS62286943A JP13125586A JP13125586A JPS62286943A JP S62286943 A JPS62286943 A JP S62286943A JP 13125586 A JP13125586 A JP 13125586A JP 13125586 A JP13125586 A JP 13125586A JP S62286943 A JPS62286943 A JP S62286943A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- liquid crystal
- crotyl
- substituted
- 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
- -1 4'-substituted biphenyl crotyl ether derivative Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 12
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 11
- 230000007704 transition Effects 0.000 abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 4
- 125000002619 bicyclic group Chemical group 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 abstract description 2
- 239000012769 display material Substances 0.000 abstract description 2
- 230000003472 neutralizing effect Effects 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 abstract description 2
- 229940031826 phenolate Drugs 0.000 abstract description 2
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- FXCXOKOKILDXCL-UHFFFAOYSA-N 1-but-2-enoxybut-2-ene Chemical class CC=CCOCC=CC FXCXOKOKILDXCL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical class C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は電気光学的表示材料として有用な新規ネマチッ
ク液晶化合物である４′−置換ビフェニルクロチルエー
テル誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to 4'-substituted biphenyl crotyl ether derivatives which are novel nematic liquid crystal compounds useful as electro-optic display materials.
液晶表示セルの代表的々ものにジー・エイチ・バイルマ
イヤー（Ｇ、ＨｌＨａｌｌｍａｌｓｒ ）等ＣＡｐｐＩ
。Representative examples of liquid crystal display cells include G.H. Beilmeyer (G, HlHallmalsr) and other CAppI
.
Ｐｈｙａ、Ｌａｔｔ＠ｒｍ、 １３ 、４６ （１９６
８））によって提案された動的散乱効果型セル（ダイナ
ミック・スキャッタリング・モード・セル）′またはエ
ム・シャツ ト （Ｍ ５ｃｈａｄｔ ）
等 （Ａｐｐｌ、Ｐｈｙｓ、Ｌｓｔｔ＠ｒｓ、１ ８
＋１２７（１９７１））によりて提案された電界効果
型セル（フィールド・エフェクト・モード・セル）また
はノー・エイチ・バイルマイヤー（Ｃ，Ｈ。Phya, Latt@rm, 13, 46 (196
8) Dynamic scattering effect type cell (dynamic scattering mode cell) or M5chadt proposed by
etc. (Appl, Phys, Lstt@rs, 1 8
+127 (1971)) or the field effect mode cell proposed by No. H. Beilmeier (C,H.
Ｈａｉ１ｍ＠ｉｅｒ ）等（Ａｐｐｌ、Ｐｈｙｓ、Ｌ＠
ｔｔｅｒａ 、 １３ 、９１（１９６８）］によって
提案されたダスト・ホスト型セル等がある。Hai1m@ier ) etc. (Appl, Phys, L@
tera, 13, 91 (1968)] and the like.
これらの液晶表示セルに用いられる液晶材料には種々の
特性が要求されるが、室温を含む広い温度範囲でネマチ
ック相を有することは各種表示セルに共通して要求され
ている重要な特性である。The liquid crystal materials used in these liquid crystal display cells are required to have various properties, but having a nematic phase over a wide temperature range including room temperature is an important property that is commonly required for all types of display cells. .
このような特性を有する実用可能な液晶材料の多くは、
通常、室温付近にネマチック相を有する化合物と室温よ
シ高い温度領域にネマチック相を有する化合物から成る
数種又はそれ以上の成分を混合することによりて調製さ
れる。現在実用的に使用される上記の如き混合液晶の多
くは、少なくとも一３０℃〜＋６５℃の全温度範囲に亘
ってネマチック相を有することが要求されているが液晶
表示セルの応用製品の多様化に伴ない、ネマチック液晶
温度範囲を更に高温側に拡張した液晶材料が要望されて
おり、このため、最近では特にネマチック相−等方性液
体相（Ｎ−Ｉ）転移温度の高いネマチック液晶化合物が
必要とされている。Many of the practical liquid crystal materials with such characteristics are
Usually, it is prepared by mixing several or more components consisting of a compound having a nematic phase near room temperature and a compound having a nematic phase in a temperature range above room temperature. Many of the above-mentioned mixed liquid crystals currently in practical use are required to have a nematic phase over the entire temperature range of -30°C to +65°C, but the application products of liquid crystal display cells are diversifying. As a result, there is a demand for liquid crystal materials that extend the nematic liquid crystal temperature range to higher temperatures, and for this reason, nematic liquid crystal compounds with a particularly high nematic phase-isotropic liquid phase (N-I) transition temperature have recently been developed. is necessary.
実用レベルにある混合液晶の多くは粘度、液晶温度範囲
等に関する種々の要求特性を滴定するために分子中に２
個の環構造を有する２環系ネマチック液晶化合物を主体
として構成されている。従りて、混合液晶のＮ−１転移
温阜を高温側に拡張するためには、高いＮ−Ｉ点を有す
るネマチック液晶化合物が必要とされる。Many of the mixed liquid crystals available at a practical level contain 2 molecules in the molecule in order to titrate various required properties such as viscosity and liquid crystal temperature range.
It is mainly composed of a bicyclic nematic liquid crystal compound having a ring structure. Therefore, in order to extend the N-1 transition temperature of the mixed liquid crystal to a high temperature side, a nematic liquid crystal compound having a high N-I point is required.
従って、本発明が解決しようとする問題点は、２環系ネ
マチック液晶化合物として比較的高いＮ−１転移温度を
有する新規ネマチック液晶化合物を提供することにある
。Therefore, the problem to be solved by the present invention is to provide a new nematic liquid crystal compound having a relatively high N-1 transition temperature as a bicyclic nematic liquid crystal compound.
本発明は、
一般式
で表わされる新規な化合物を提供することにより前記問
題点を解決した。The present invention has solved the above problems by providing a novel compound represented by the general formula.
本発明に係る式（１）の化合物は次の製造方法に従って
製造することができる。但し、下記の式（ＩＩ）におけ
るＲは、式（１）におけるＲと同じ意味をもつ。The compound of formula (1) according to the present invention can be produced according to the following production method. However, R in the following formula (II) has the same meaning as R in formula (1).
式（ＩＩ）の化合物に、エタノールの如き有様溶媒中で
、水酸化カリウムの如きアルカリを反応させてフェノラ
ートとするかまたは炭酸カリウムの如き炭酸塩を中和剤
として加え、これに式（Ｂの塩化クロチルの如きハロり
ン化クロチルを反応させて本発明に係る式（１）の化合
物を製造する。A compound of formula (II) is reacted with an alkali such as potassium hydroxide in a specific solvent such as ethanol to form a phenolate, or a carbonate such as potassium carbonate is added as a neutralizing agent to form a compound of formula (B). The compound of formula (1) according to the present invention is prepared by reacting a crotyl halophosphate such as crotyl chloride.
斯くして製造された式（１）の代表的な化合物の転移温
度を第１表に掲げる。Table 1 lists the transition temperatures of representative compounds of formula (1) thus produced.
□
第１表
＆ Ｒ転移温度（Ｃ）
１ ＮミＣ−９６（Ｃ−＋Ｎ） １０１（Ｎ−
＋Ｉ）第１表に掲示したデータから本発明の４１の化合
物のＮ−Ｉ転移温度は１０１℃であり、対応する従来公
知の類似化合物である式
移温度７５．５℃よシも２５．５℃高い。□ Table 1 & R transition temperature (C) 1 Nmi C-96 (C-+N) 101 (N-
+I) From the data listed in Table 1, the N-I transition temperature of the 41 compounds of the present invention is 101°C, and the formula transition temperature of the corresponding conventionally known similar compound is 75.5°C. ℃ high.
以上の比較からもわかるように本発明に係る式（１）の
化合物は、同じ分子骨格をもつ従来公知の類似化合物よ
シも高いＮ−Ｉ転移温度を有していることがわかる。As can be seen from the above comparison, the compound of formula (1) according to the present invention has a higher N-I transition temperature than conventionally known similar compounds having the same molecular skeleton.
本発明に係る式（１）の化合物は正の誘電率異方性を有
するネマチック液晶化合物であシ、従って例えば、負の
誘電率異方性を有する他のネマチック液晶化合物との混
合物の状態で動的光散乱型表示セルの材料として使用す
ることができ、また正または負の誘電率異方性を有する
他のネマチック液晶化合物との混合物の状態で電界効果
型表示セルの材料として使用することができる。The compound of formula (1) according to the present invention is a nematic liquid crystal compound having positive dielectric constant anisotropy, and therefore, for example, in the state of a mixture with another nematic liquid crystal compound having negative dielectric constant anisotropy. It can be used as a material for dynamic light scattering type display cells, and can also be used as a material for field effect type display cells in a mixture with other nematic liquid crystal compounds having positive or negative dielectric constant anisotropy. Can be done.
このように、式（１）の化合物と混合して使用すること
のできる好ましい代表例としては、例えば４−置換安息
香酸４′−置換フェニルエステル、４−置換シクａヘキ
サンカルゴン酸４’−ｆ！換フェニルエステル、４−置
換シクロヘキサンカルボン酸４’−［換ビフェニルエス
テル、４−（４−１ｉ換シクロヘキサンカルボニルオキ
シ）安息香酸４′−置換フェニルエステル、４−（４−
置換シクロヘキシル） 安息香酸４’ −Ｍ換フェニル
エステル、４−（４−置換シクロヘキシル）安息香酸４
′−置換シクロヘキシルエステル、４−ｆｆｉ換４’−
置換ヒフェニル、４−ｆｆｉ換フェニル−４’−ｆｆｍ
シクロヘキサン、４−置換４′−置換ターフェニル、４
−置換ピフェニル４′−置換シクロヘキサン、２−（４
−ｆｆｉ換フェニル）−５−置換ピリミジンなどを挙げ
ることができる。Thus, preferred representative examples which can be used in combination with the compound of formula (1) include, for example, 4-substituted benzoic acid 4'-substituted phenyl ester, 4-substituted cyclohexanecargonic acid 4'-f ! substituted phenyl ester, 4-substituted cyclohexanecarboxylic acid 4'-[substituted biphenyl ester, 4-(4-1i substituted cyclohexanecarbonyloxy)benzoic acid 4'-substituted phenyl ester, 4-(4-
(substituted cyclohexyl)benzoic acid 4'-M substituted phenyl ester, 4-(4-substituted cyclohexyl)benzoic acid 4
'-substituted cyclohexyl ester, 4-ffi substituted 4'-
substituted hiphenyl, 4-ffi substituted phenyl-4'-ffm
Cyclohexane, 4-substituted 4'-substituted terphenyl, 4
-substituted piphenyl 4'-substituted cyclohexane, 2-(4
Examples include -ffi-substituted phenyl)-5-substituted pyrimidine.
実施例１
４′−ヒドロキシ−４−シアノビフェニル１．０．９（
５，１ｍｍｏｔ）をアセトｙｌ□＋ｔＡｆに溶解させ、
無水炭酸カリウム０．８４７ｉ （６，１ｍｍｏｔ）を
加えて、これらを攪拌しながら還流温度で、トランス塩
化りロチｋ Ｏ，，７０１（７，７ｍｍｏｔ）を滴下し
た後、さらに同温度で５時間反応させた。Example 1 4'-hydroxy-4-cyanobiphenyl 1.0.9 (
5,1 mmot) was dissolved in acetyl□+tAf,
0.847 i (6.1 mmot) of anhydrous potassium carbonate was added, and while stirring the mixture, trans-chlorinated roti-k O,,701 (7.7 mmot) was added dropwise at reflux temperature, followed by further reaction at the same temperature for 5 hours. I let it happen.
冷却後、反応混合物に水を加えて反応生成物をエーテル
で抽出し、抽出液を水洗、乾燥後、この液からエーテル
を留去した。After cooling, water was added to the reaction mixture, the reaction product was extracted with ether, the extract was washed with water, and after drying, the ether was distilled off from this liquid.
得られた反応生成物をエタノールから再結晶させて精製
し、さらにｎ−ヘキサンから再結晶させて精製して、−
下記化合物０．７０１ （２，８ｍｍｏｔ）を得た。The obtained reaction product was purified by recrystallization from ethanol, further purified by recrystallization from n-hexane, and -
The following compound 0.701 (2.8 mmot) was obtained.
収率５５チ
転移温度 ９６℃（ＣＡＮ）
１０１℃（Ｎｆ”Ｉ）
〔発明の効果〕
本発明の４−置換ピフェニルクロチルエーテル誘導体は
、２環系ネマチック液晶化合物としては比較的高いＮ−
Ｉ点を有する。従って、本発明の化合物の使用によって
、駆動温度範囲を高温側に拡張した液晶表示セルを製作
することができる。Yield: 55°C Transition temperature: 96°C (CAN) 101°C (Nf”I) [Effects of the invention] The 4-substituted piphenyl crotyl ether derivative of the present invention has a relatively high N-
It has an I point. Therefore, by using the compound of the present invention, it is possible to manufacture a liquid crystal display cell whose driving temperature range is extended to the high temperature side.
Claims (1)
素原子数１〜９の直鎖状アルコキシ基またはシアノ基を
表わし、クロチル基はトランス配置である。］ で表わされる化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R is a linear alkyl group having 1 to 9 carbon atoms, a linear alkoxy group having 1 to 9 carbon atoms, or It represents a cyano group, and the crotyl group is in the trans configuration. ] A compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13125586A JPS62286943A (en) | 1986-06-06 | 1986-06-06 | 4'-substituted biphenyl crotyl ether derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13125586A JPS62286943A (en) | 1986-06-06 | 1986-06-06 | 4'-substituted biphenyl crotyl ether derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62286943A true JPS62286943A (en) | 1987-12-12 |
Family
ID=15053636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13125586A Pending JPS62286943A (en) | 1986-06-06 | 1986-06-06 | 4'-substituted biphenyl crotyl ether derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62286943A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02231460A (en) * | 1989-03-03 | 1990-09-13 | Adeka Argus Chem Co Ltd | Alkenoxycyanobiphenyl compound |
| JP2012524836A (en) * | 2009-06-18 | 2012-10-18 | ケムチュア コーポレイション | Aryl alkenyl ether oligomers and polymers and their use in the production of flame retardants |
-
1986
- 1986-06-06 JP JP13125586A patent/JPS62286943A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02231460A (en) * | 1989-03-03 | 1990-09-13 | Adeka Argus Chem Co Ltd | Alkenoxycyanobiphenyl compound |
| JP2012524836A (en) * | 2009-06-18 | 2012-10-18 | ケムチュア コーポレイション | Aryl alkenyl ether oligomers and polymers and their use in the production of flame retardants |
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