JP2822529B2 - Ether-based thinning liquid crystal - Google Patents
Ether-based thinning liquid crystalInfo
- Publication number
- JP2822529B2 JP2822529B2 JP2015480A JP1548090A JP2822529B2 JP 2822529 B2 JP2822529 B2 JP 2822529B2 JP 2015480 A JP2015480 A JP 2015480A JP 1548090 A JP1548090 A JP 1548090A JP 2822529 B2 JP2822529 B2 JP 2822529B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- substituted
- formula
- ether
- 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 - Fee Related
Links
- 239000004973 liquid crystal related substance Substances 0.000 title description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- -1 4-substituted benzoic acid Chemical class 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000004988 Nematic liquid crystal Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 4
- 230000005669 field effect Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 239000012769 display material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は電気光学的表示材料として有用な新規のエー
テル系減粘性液晶に関する。Description: TECHNICAL FIELD The present invention relates to a novel ether thinning liquid crystal useful as an electro-optical display material.
液晶表示セルの代表的なものにエム・シャット（M.Sc
hadt）等〔APPLIED PHYSICS LETTERS 18,127〜128（197
1）〕によっ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）又はジー・エイチ・ハイ
ルマイヤー（G.H.Heilmeier）等〔PROCEEDING OF I.E.
E.E.56,1162〜1171（1968）〕によって提案された動的
光散乱型セル（ダイナミック・スキャッタリング・モー
ド・セル）又はジー・エイチ・ハイルマイヤー（G.H.He
ilmeier）等〔APPLIED PHYSICS LETTERS 13,91（198
6）〕あるいはディー・エル・ホワイト（D.L.White）等
〔JOURNAL OF APPLIED PHYSICS 45,4718（1974）〕によ
って提案されたゲスト・ホスト型セルなどがある。A typical liquid crystal display cell is M-Shut (M.Sc
hadt) etc. [APPLIED PHYSICS LETTERS 18 , 127-128 (197
1)] [PROCEEDING OF IE] such as a field effect cell (field effect mode cell) or GH Heilmeier proposed by
EE 56 , 1162-1171 (1968)], or a dynamic light scattering type cell (dynamic scattering mode cell) or GH Heilmeier (GHHe).
ilmeier) etc. [APPLIED PHYSICS LETTERS 13 , 91 (198
6)] or a guest-host type cell proposed by DL White etc. [JOURNAL OF APPLIED PHYSICS 45 , 4718 (1974)].
これらの液晶表示セルには、種々の特性が要求されて
いるが、広い温度範囲で駆動可能なことと、高速応答性
は特に重要な要求特性である。These liquid crystal display cells are required to have various characteristics, but the ability to be driven in a wide temperature range and high-speed response are particularly important characteristics.
液晶組成物のネマチック相−等方性液体相転移温度
（以下、Ｎ−Ｉ点という。）を上昇させ、同時に粘度を
低下させる化合物は、車載用液晶表示セルや液晶テレビ
に有用な液晶材料である。特に応答時間（τ）は液晶材
料の粘度（η）と比例関係（τ∝η）にあることから、
粘度の低い液晶材料を使用すれば、高速応答性に優れた
液晶表示セルを作製することができる。Compounds that increase the nematic phase-isotropic liquid phase transition temperature (hereinafter referred to as the NI point) of a liquid crystal composition and at the same time lower the viscosity are useful liquid crystal materials for in-vehicle liquid crystal display cells and liquid crystal televisions. is there. In particular, since the response time (τ) is proportional to the viscosity (η) of the liquid crystal material (τ∝η),
When a liquid crystal material having a low viscosity is used, a liquid crystal display cell excellent in high-speed response can be manufactured.
現在、このような目的で用いられている優れた粘度低
下剤には で表わせる化合物等がある。At present, excellent viscosity reducing agents used for such purposes include: And the like.
しかしながら、上記の化合物（ａ）は、液晶組成物の
粘度を低下させることができるが、同時にＮ−Ｉ点も低
下させるという問題点を有していた。However, the compound (a) has a problem that the viscosity of the liquid crystal composition can be reduced, but the NI point is also lowered at the same time.
本発明が解決しようとする課題は、現在、ネマチック
液晶材料として汎用されている母体液晶に添加した場
合、母体液晶のＮ−Ｉ点を上昇させ、且つ粘度を効果的
に低下せしめる新規化合物を提供することにある。The problem to be solved by the present invention is to provide a novel compound which, when added to a base liquid crystal which is currently widely used as a nematic liquid crystal material, increases the NI point of the base liquid crystal and effectively lowers the viscosity. Is to do.
本発明は、上記課題を解決するために、一般式 （式中、R1及びR2は各々独立的に炭素原子数１〜７の直
鎖状アルキル基を表わし、ｎは３〜５の整数を表わし、 はトランス（エカトリアル−エカトリアル）配置のシク
ロヘキサン環を表わす。） で表わされる化合物を提供する。The present invention provides a compound represented by the general formula (Wherein, R 1 and R 2 each independently represent a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 3 to 5, Represents a cyclohexane ring in a trans (equatorial-equatorial) configuration. ) Is provided.
本発明に係わる式（Ｉ）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。The compound of the formula (I) according to the present invention can be produced according to the following production method.
（式中、R1及びR2は各々独立的に炭素原子数１〜７の直
鎖状アルキル基を表わし、ｎは３〜５の整数を表わし、 はトランス（エカトリアル−エカトリアル）配置のシク
ロヘキサン環を表わす。） 第１段階−式（II）の化合物とｔ−ブチルメチルエーテ
ル中で式（III）の化合物を強塩基で処理して得られる
イリドと反応させて式（IV）の化合物を製造する。 (Wherein, R 1 and R 2 each independently represent a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 3 to 5, Represents a cyclohexane ring in a trans (equatorial-equatorial) configuration. 1) Step 1-A compound of formula (IV) is prepared by reacting a compound of formula (II) with an ylide obtained by treating a compound of formula (III) with a strong base in t-butyl methyl ether.
第２段階−式（IV）の化合物を酢散エチル中、ラネーニ
ッケルを触媒として接触還元を行ない化合物（Ｉ）を製
造する。Second step-The compound of formula (IV) is subjected to catalytic reduction in ethyl acetate and Raney nickel as a catalyst to produce compound (I).
斯くして製造された式（Ｉ）の化合物の代表的なもの
の相転移温度を第１表に掲げる。Table 1 lists the phase transition temperatures of representatives of the compounds of formula (I) thus prepared.
本発明に係る式（Ｉ）の化合物は、例えば、正又は負
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
混合物と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 the formula (I) according to the present invention can be used as a material for a field effect display cell in a state of, for example, a mixture with another nematic liquid crystal compound having a positive or negative dielectric anisotropy. .
このように、式（Ｉ）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−置換シクロヘ
キサンカルボン酸４′−置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′−置換ビフェニルエス
テル、４−（４−置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′−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′−
置換シクロヘキシルエステル、４−置換４′−置換ビフ
ェニル、４−置換フェニル−４′−置換シクロヘキサ
ン、４−置換４″−置換ターフェニル、４−置換ビフェ
ニル４′−置換シクロヘキサン、２−（４′−置換フェ
ニル）−５−置換ピリミジンなどを挙げることができ
る。Thus, preferable representative examples which can be used as a mixture with the compound of the formula (I) include, for example, 4-substituted benzoic acid 4'-substituted phenyl ester and 4-substituted cyclohexanecarboxylic acid 4'-substituted phenyl ester 4-substituted cyclohexanecarboxylic acid 4'-substituted biphenyl ester, 4- (4-substituted cyclohexanecarbonyloxy) benzoic acid 4'-substituted phenyl ester, 4- (4-
Substituted cyclohexyl) benzoic acid 4'-substituted phenyl ester, 4- (4-substituted cyclohexyl) benzoic acid 4'-
Substituted cyclohexyl ester, 4-substituted 4'-substituted biphenyl, 4-substituted phenyl-4'-substituted cyclohexane, 4-substituted 4 "-substituted terphenyl, 4-substituted biphenyl 4'-substituted cyclohexane, 2- (4'- (Substituted phenyl) -5-substituted pyrimidine and the like.
第２表は時分割駆動特性の優れたネマチック液晶材料
として現在汎用されている母体液晶（Ａ）の75重量％と
第１表に示した式（Ｉ）の化合物No.1の25重量％とから
成る各混合液晶について測定されたＮ−Ｉ点と粘度を掲
示し、比較のために母体液晶（Ａ）75重量％と優れた粘
度低下剤として一般的に使用されている下記の化合物
（ａ）の25重量％とから成る混合液晶について測定され
たＮ−Ｉ点と粘度を掲示したものである。尚、母体液晶
（Ａ）は、 から成るものであり、化合物（ａ）は、次式で表わされ
るものである。Table 2 shows that 75% by weight of the parent liquid crystal (A), which is currently widely used as a nematic liquid crystal material having excellent time-sharing driving characteristics, and 25% by weight of the compound No. 1 of the formula (I) shown in Table 1. The measured NI points and viscosities of each mixed liquid crystal composed of the following are shown. For comparison, the parent compound (A) was 75% by weight and the following compound (a) generally used as an excellent viscosity reducing agent was used. 2) shows the measured NI point and viscosity of a mixed liquid crystal composed of 25% by weight of (a). The mother liquid crystal (A) is Wherein the compound (a) is represented by the following formula:
第２表から化合物（ａ）と比較し式（Ｉ）の化合物
は、母体液晶（Ａ）のＮ−Ｉ点を上昇させ、且つ粘度を
効果的に低下させしめることが理解できる。 From Table 2, it can be seen that the compound of formula (I) increases the NI point of the base liquid crystal (A) and effectively lowers the viscosity as compared with the compound (a).
実施例１ 19.5g（0.054モル）をｔ−ブチルメチルエーテル80mlに
加え、−５℃で撹拌下、カリウム−ｔ−ブトキシサイド
7.8g（0.07モル）で処理した後、１時間室温で撹拌し
た。次いで、この反応混合物を０℃に冷却した後、式 の化合物8.9g（0.04モル）のテトラヒドロフラン溶液25
mlを滴下し、２時間反応させた。Example 1 19.5 g (0.054 mol) was added to t-butyl methyl ether (80 ml), and the mixture was stirred at -5 ° C with potassium-t-butoxide.
After treating with 7.8 g (0.07 mol), the mixture was stirred at room temperature for 1 hour. Then, after cooling the reaction mixture to 0 ° C., the formula Of 8.9 g (0.04 mol) of a compound in tetrahydrofuran 25
ml was added dropwise and reacted for 2 hours.
反応終了後、反応混合物に水80mlを加えた後、反応生
成物を酢酸エチル80mlで２回抽出した。抽出液を水洗、
乾燥した後、溶媒を減圧留去して得た残渣をカラムクロ
マトグラフィーを用いて精製して、下記化合物8.4g（0.
03モル）を得た。After completion of the reaction, 80 ml of water was added to the reaction mixture, and the reaction product was extracted twice with 80 ml of ethyl acetate. Wash the extract with water,
After drying, the residue obtained by evaporating the solvent under reduced pressure was purified by column chromatography, and 8.4 g of the following compound (0.
03 mol).
上記化合物8.4g（0.03モル）を酢酸エチル200mlに溶
解し、この溶液にラネーニッケル1gを加えた後、水素圧
５気圧で接触還元した。 8.4 g (0.03 mol) of the above compound was dissolved in 200 ml of ethyl acetate, and 1 g of Raney nickel was added to this solution, followed by catalytic reduction at a hydrogen pressure of 5 atm.
還元終了後、触媒をろ別し、溶媒を減圧留去して得た
残渣をエタノールから再結晶させて精製して、下記化合
物4g（0.014モル）を得た。After completion of the reduction, the catalyst was filtered off, the solvent was distilled off under reduced pressure, and the residue obtained was purified by recrystallization from ethanol to obtain 4 g (0.014 mol) of the following compound.
移転温度 29℃ （Ｃ→Ｓ） 88℃ （ＳＩ） 〔発明の効果〕 本発明に係わる式（Ｉ）の化合物は、現在ネマチック
液晶組成物として汎用されている母材液晶に混合するこ
とによって、母体液晶のネマチック相−等方性液体相転
移温度を上昇させ、且つ粘度を効果的に低下せしめるこ
とができる。 Transfer temperature 29 ° C. (C → S) 88 ° C. (SI) [Effect of the Invention] The compound of the formula (I) according to the present invention can be mixed with a base liquid crystal which is currently widely used as a nematic liquid crystal composition. The nematic phase-isotropic liquid phase transition temperature of the base liquid crystal can be increased, and the viscosity can be effectively reduced.
特に式（Ｉ）化合物は粘度低下剤として用いられてい
る公知の代表的化合物（ａ）と比較し、母材液晶のネマ
チック相−等方液体相転移温度の改良に優れた特徴を示
す。In particular, the compound of the formula (I) is superior to the well-known typical compound (a) used as a viscosity-lowering agent in that the compound has excellent characteristics in improving the nematic phase-isotropic liquid phase transition temperature of the base liquid crystal.
また、現在汎用されているネマチック液晶組成物との
相溶性にも優れている。Further, it is excellent in compatibility with a nematic liquid crystal composition which is currently widely used.
従って、本発明の式（Ｉ）の化合物は、広域温度で駆
動可能で、高速応答性を要求される車載用、テレビ、ワ
ープロなどの液晶表示セルの材料とし有用である。Therefore, the compound of the formula (I) of the present invention is useful as a material for a liquid crystal display cell such as an in-vehicle device, a television, a word processor, etc., which can be driven at a wide temperature range and requires a high response speed.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 43/115 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 6 , DB name) C07C 43/115 CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (1)
鎖状アルキル基を表わし、ｎは３〜５の整数を表わし、 はトランス（エカトリアル−エカトリアル）配置のシク
ロヘキサン環を表わす。） で表わされる化合物。(1) General formula (Wherein, R 1 and R 2 each independently represent a linear alkyl group having 1 to 7 carbon atoms, n represents an integer of 3 to 5, Represents a cyclohexane ring in a trans (equatorial-equatorial) configuration. ) The compound represented by these.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015480A JP2822529B2 (en) | 1990-01-25 | 1990-01-25 | Ether-based thinning liquid crystal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015480A JP2822529B2 (en) | 1990-01-25 | 1990-01-25 | Ether-based thinning liquid crystal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03220145A JPH03220145A (en) | 1991-09-27 |
| JP2822529B2 true JP2822529B2 (en) | 1998-11-11 |
Family
ID=11889957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015480A Expired - Fee Related JP2822529B2 (en) | 1990-01-25 | 1990-01-25 | Ether-based thinning liquid crystal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2822529B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4748339B2 (en) * | 2001-01-26 | 2011-08-17 | Ｄｉｃ株式会社 | Methylenecyclohexane derivative |
-
1990
- 1990-01-25 JP JP2015480A patent/JP2822529B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03220145A (en) | 1991-09-27 |
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