CN1928004A - Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof - Google Patents

Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof Download PDF

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CN1928004A
CN1928004A CN 200610139011 CN200610139011A CN1928004A CN 1928004 A CN1928004 A CN 1928004A CN 200610139011 CN200610139011 CN 200610139011 CN 200610139011 A CN200610139011 A CN 200610139011A CN 1928004 A CN1928004 A CN 1928004A
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allyloxy
liquid crystal
carboxylic acid
fluoro
azobenzene
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CN 200610139011
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CN100410347C (en )
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张书圣
任锐
颜连忠
黄学青
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青岛科技大学
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Abstract

The present invention relates to one kind of substituted azophenyl carboxylate containing fluorine atom and cyan group as liquid crystal compound and its preparation process. The compound has the chemical structure of 4'-allyloxy-4- azophenyl carboxylic acid-3-fluoro-4-cyan phenyl ester. The preparation process includes the first Williamson etherification to introduce allyloxy radical to the 4'-place of p-hydroxy azophenyl carboxylic acid so as to produce 4'-allyloxy-4-azophenyl carboxylic acid; and the subsequent DCC dehydrating condensation of 4'-allyloxy-4-azophenyl carboxylic acid and 2-fluoro-4-hydroxyl phenyl nitrile to obtain the required compound. The present invention also relates to the use of the compound, and the monomer liquid crystal compound may be used in compounding composite liquid crystal for LCD.

Description

液晶化合物—4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯及其制备方法 The liquid crystal compound 4'-allyloxy-4-carboxylic acid azobenzene 4-cyano-3-fluoro-phenyl ester and preparation method

技术领域 FIELD

本发明涉及有机合成技术领域,尤其是涉及一种含有氟原子和氰基的取代偶氮苯羧酸酯类液晶化合物及制备方法和用途。 The present invention relates to a technical field of organic synthesis, particularly to substituted azobenzene liquid crystal compound and carboxylic acid esters and the use of a preparation containing a fluorine atom and a cyano group.

背景技术 Background technique

近年来,液晶化合物和液晶材料成为应用化学和材料化学研究的热点之一,在电子学、光学、声学、生物工程、化学工业等各方面得到了广泛的应用,而其中最广泛和最重要的是它在电子显示方面的应用。 In recent years, a liquid crystal compound and a liquid crystal material to one of applied chemistry and chemistry of the hot material, has been widely used in various aspects of the electronics, optical, acoustical, biological engineering, chemical industry and the like, but the most important and widely it is used in electronic display area. 随着信息产业的发展,对液晶材料的要求也在不断的提高。 With the development of information industry, the requirements for liquid crystal materials is constantly improving. 虽然有关液晶材料方面的报道已有很多,但它们并不全部适合用于显示器件中,因为显示用的液晶材料必须满足较宽工作温度范围、较低的工作电压、低黏度、快速响应、高稳定性等要求。 Although the reports of the liquid crystal material has many aspects, but they are not all suitable for use in display devices, since the liquid crystal display material must meet a wide operating temperature range, low operating voltage, low viscosity, quick response, high stability requirements.

以2-氟-4-羟基苯腈为中间体的液晶化合物兼有含氟液晶和氰基液晶的优点,是满足上述条件、代表液晶发展趋势的一类重要的液晶化合物,而2-氟-4-羟基苯腈也因此成为液晶化学工业中重要的中间体。 2-fluoro-4-hydroxybenzonitrile of the intermediate liquid crystal compound combines the advantages of a fluorine-containing liquid crystal and a cyano group, the above condition is satisfied, representing the development trend of a liquid crystal important class of liquid crystal compounds, and 2-fluoro - 4- hydroxybenzonitrile liquid chemical industry has also become an important intermediate. 该中间体最早在1982年由日本Sumitomo Chemical Co.Ltd.首先合成,此后人们使用该中间体合成了数百种液晶化合物,这些化合物都具有高清亮点、宽液晶工作范围、低黏度的优点,适合作为性能优良的显示液晶材料的组成成分。 The first intermediate, first synthesized in 1982 by Japan Sumitomo Chemical Co.Ltd, after the synthesis of Intermediate people use hundreds of liquid crystal compounds which have a high clearing point, broad liquid crystal range of work, the advantages of low viscosity, for excellent display performance as a component of the liquid crystal material.

发明内容 SUMMARY

本发明的目的是提供一种含有氟原子和氰基的取代偶氮苯羧酸酯类液晶化合物,其结构式为 Object of the present invention is to provide a containing fluorine atoms and cyano-substituted carboxylic acid esters azobenzene liquid crystal compound having the formula 该化合物具有化学性质稳定、清亮点高、液晶范围宽的优点,是潜在的液晶显示材料的组成成分和光电转换材料组成成分。 The compound having chemical stability, a high clearing point, broad liquid crystal range of advantages, the liquid crystal display potential photoelectric conversion material composition and material composition.

该化合物是通过有机合成技术制成的。 This compound is made by the techniques of organic synthesis. 合成该化合物的方法的要点为:1)以乙醇-水溶液为混合溶剂,其中乙醇的体积百分比为70%~95%;加入可溶性碱金属氢氧化物使溶液的酸碱度达到pH>10,在溶剂中加入3-卤代丙烯(所谓“卤代”系指氟取代、氯取代、溴取代或碘取代)和对羟基偶氮苯羧酸,两者的物质的量之比为2~5∶1,对羟基偶氮苯羧酸在溶液中的质量分数为5%~30%。 The method of synthesis of this compound points are: 1) ethanol - a mixed solvent solution, wherein the volume percent of ethanol is 70% to 95%; soluble alkali metal hydroxide is added that the pH of the solution to pH> 10, in a solvent was added 3-halogenated propenyl (so-called "halo" refers to fluoro-substituted, chloro-substituted, bromine-substituted or iodine-substituted) and p-hydroxybenzoic acid azobenzene, both the amount of substance ratio of 2 ~ 5:1, azobenzene mass fraction of hydroxy acid in the solution is from 5% to 30%. 在这一条件下,使两者发生缩合反应。 Under this condition, so that both the condensation reaction. 反应温度为50~80℃。 The reaction temperature is 50 ~ 80 ℃.

2)缩合反应完毕后,用可溶性碱金属氢氧化物的乙醇-水混合溶剂溶液与上一步反应所得的混合液反应,通过水解反应除去步骤1)中生成的副产物,制得纯的4'-烯丙氧基-4-偶氮苯羧酸。 2) After completion of the condensation reaction with a soluble alkali metal hydroxide in ethanol - water mixed solvent solution of step is reacted with a mixture of the resultant reaction by-products in the hydrolysis reaction step 1) removing the formed, to give the pure 4 ' - azobenzene-allyloxy-4-carboxylic acid. 所用的可溶性氢氧化物与步骤1)中所使用的对羟基偶氮苯羧酸的物质的量之比为2~5∶1,反应体系的pH>12,反应温度为50~80℃,混合溶剂中乙醇的体积百分比为60%~80%。 Hydroxide and soluble step used the ratio of the amount of substance of hydroxyl acid is an azobenzene) used 2 ~ 5:1, pH of the reaction system is> 12, the reaction temperature is 50 ~ 80 ℃, mixed the volume percentage of ethanol in the solvent is 60% to 80%.

3)以DCC(N,N-二环己基碳二亚胺)为脱水剂,DMAP(N,N-二甲氨基吡啶)为催化剂,无水四氢呋喃为溶剂,促使4'-烯丙氧基-4-偶氮苯羧酸和2-氟-4-羟基苯腈通过脱水缩合反应,生成目标化合物4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯。 3) DCC (N, N- dicyclohexyl carbodiimide) as a dehydrating agent, DMAP (N, N- dimethylaminopyridine) as a catalyst, in anhydrous tetrahydrofuran as a solvent to promote 4'-allyloxy - azobenzene 4- carboxylic acid and 2-fluoro-4-hydroxybenzonitrile by dehydration condensation reaction to produce the title compound 4'-allyloxy-4-fluoro-4-carboxylic acid azobenzene cyanophenyl ester. DCC、4'-烯丙氧基-4-偶氮苯羧酸、2-氟-4-羟基苯腈、DMAP的物质的量之比为1~1.5∶1~2∶1∶0.01~0.02,2-氟-4-羟基苯腈在溶液中的起始质量分数为5%~20%。 DCC, 4'- azobenzene-allyloxy-4-carboxylic acid, 2-fluoro-4-hydroxybenzonitrile, the ratio of the amount of substance of DMAP is 1.5 ~ 1 ~ ~ 2:1:0.01 0.02, fluoro-4-hydroxybenzonitrile starting content in the solution is from 5% to 20%. 反应温度为0~30℃。 The reaction temperature is 0 ~ 30 ℃.

通过以下实验将有助于理解本发明,但以下实验不限制本发明的内容。 By following experiments will assist in understanding the invention, but not limit the present experiments the following invention.

实施11)将0.01mol对羟基偶氮苯羧酸与0.02mol氢氧化钾溶于40ml 95%(体积分数)乙醇中,以约1ml/min的速度逐滴加入0.03mol 3-溴丙烯,回流反应24h,再加入0.02mol氢氧化钾的70%(体积分数)乙醇溶液计14ml,继续回流2h。 Embodiment 11) The p-hydroxy azobenzene 0.01mol acid and 0.02mol of potassium hydroxide was dissolved in 40ml 95% (volume fraction) of ethanol at a rate of about 1ml / min added dropwise 0.03mol 3- bromo-propene, reflux 24h, then added 70% 0.02mol of potassium hydroxide (by volume) ethanol solution count 14ml, continue refluxed for 2h. 加入水100ml,浓盐酸20ml,加热15min后,冷却过滤,以蒸馏水洗涤、干燥,再以95%(体积分数)乙醇重结晶,得到4'-烯丙氧基-4-偶氮苯羧酸,为橙红色片状晶体,产率44%。 Water was added 100ml, 20ml of concentrated hydrochloric acid, heated 15min, cooled and filtered, washed with distilled water, dried, and then 95% (volume fraction) and recrystallized from ethanol to give 4'-allyloxy-4-carboxylic acid azobenzene, flaky orange-red crystals, 44% yield.

2)在三口烧瓶中加入0.01mol 4'-烯丙氧基-4-偶氮苯羧酸和20ml无水四氢呋喃,搅拌使其完全溶解后,加入0.01mol的DCC(N,N-二环己基碳二亚胺),待出现混浊现象后,将0.01mol 2-氟-4-羟基苯腈和少量DMAP[4-(N,N-二甲氨基)吡啶]溶解在20ml无水四氢呋喃中配成溶液,缓慢滴入烧瓶中,在10℃左右搅拌24h,反应完毕后,过滤除去副产物N,N-二环己基脲,在滤液中加蒸馏水使产物沉淀出来,干燥后通过柱层析分离得纯品0.68g,产率约17%。 2) was added 0.01mol 4'-allyloxy-4- three-necked flask and 20ml azobenzene acid anhydrous tetrahydrofuran, stirred and completely dissolved, added 0.01mol of DCC (N, N- dicyclohexyl after carbodiimide), until turbidity appears, 0.01mol 2- fluoro-4-hydroxybenzonitrile and a small amount of DMAP [4- (N, N- dimethylamino) pyridine] was dissolved in 20ml of anhydrous tetrahydrofuran was formulated solution was slowly dropped into the flask and stirred at about 10 ℃ 24h, after completion of the reaction, the product was removed by filtration and N, N- dicyclohexylurea, distilled water was added to the filtrate to precipitate the product was isolated after drying by column chromatography pure 0.68g, yield about 17%.

实施21)将0.02mol对羟基偶氮苯羧酸与0.06mol氢氧化钾溶于100ml95%(体积分数)乙醇中,再加入0.05mol 3-碘丙烯,回流反应60h。 Embodiment 21) The p-hydroxy azobenzene 0.02mol and 0.06mol of potassium hydroxide dissolved in acid 100ml95% (volume fraction) of ethanol, then added 0.05mol 3- iodo-propylene, the reaction was refluxed for 60h. 之后加入0.03mol氢氧化钾的70%(体积分数)乙醇溶液计35ml,继续回流2h。 After addition of 0.03mol of potassium hydroxide 70% (by volume) ethanol solution count 35ml, continue refluxed for 2h. 加入水100ml,浓盐酸40ml,混合均匀,加热20min后,冷却过滤,以蒸馏水洗涤、干燥,再以95%(体积分数)乙醇重结晶,得到4'-烯丙氧基-4-偶氮苯羧酸,为橙红色片状晶体,产率40%。 Water was added 100ml, concentrated hydrochloric acid 40ml, mixed, heating after 20min, cooled and filtered, washed with distilled water, dried, and then 95% (volume fraction) was recrystallized from ethanol to give 4'-allyloxy-4-azobenzene acid, orange-red flake crystals, yield 40%.

2)在三口烧瓶中加入0.015mol 4'-烯丙氧基-4-偶氮苯羧酸和50ml无水四氢呋喃,搅拌使其完全溶解后,加入0.01mol的DCC(N,N-二环己基碳二亚胺),待出现混浊现象后,将0.015mol 2-氟-4-羟基苯腈和少量DMAP[4-(N,N-二甲氨基)吡啶]完全溶解在35ml无水四氢呋喃中配成溶液,缓慢滴入烧瓶中,在20℃左右搅拌24h,反应完毕后,过滤除去副产物N,N-二环己基脲,在滤液中加蒸馏水使产物沉淀出来,干燥后通过柱层析分离得纯品0.91g,产率约15%。 2) Add 0.015mol 4'- three-necked flask allyloxy-4- azobenzene-carboxylic acid and 50ml of dry tetrahydrofuran, stirred and completely dissolved, added 0.01mol of DCC (N, N- dicyclohexyl after carbodiimide), until turbidity appears, 0.015mol 2- fluoro-4-hydroxybenzonitrile and a small amount of DMAP [4- (N, N- dimethylamino) pyridine] completely dissolved in 35ml of anhydrous tetrahydrofuran with as a solution, was slowly dropped into the flask and stirred at about 20 ℃ 24h, after completion of the reaction, the product was removed by filtration and N, N- dicyclohexylurea, distilled water was added to the filtrate to precipitate the product was isolated by column chromatography after drying to give pure product 0.91g, 15% yield.

通过IR,1H NMR方法对所合成的化合物进行表征,以确认其结构。 , 1H NMR methods the synthesized compounds were characterized by IR, to confirm their structures.

IR(红外光谱): IR (infrared spectrum): 氰基(1,C≡N键伸缩振动,2243cm-1)苯环(2,苯环碳骨架伸缩振动,1603,1501cm-1)羰基(3,C=O伸缩振动,1739cm-1)碳氧单键(4,COC伸缩振动,1251,1146cm-1)1HNMR(核磁共振氢谱): Cyano (1, C≡N stretching vibration, 2243cm-1) a benzene ring (2, carbon skeleton stretching vibration of a benzene ring, 1603,1501cm-1) a carbonyl group (3, C = O stretching vibration, 1739cm-1) carboxyhemoglobin a single bond (4, COC stretching vibration, 1251,1146cm-1) 1HNMR (H NMR): 质子1:δ=7.20×10-6,2H质子2:δ=7.97×10-6,2H Proton 1: δ = 7.20 × 10-6,2H protic 2: δ = 7.97 × 10-6,2H

质子3:δ=8.03×10-6,2H质子4:δ=8.34×10-6,2H质子5:δ=7.51×10-6,1H质子6:δ=7.78×10-6,1H质子7:δ=8.12×10-6,1H质子8:δ=5.32~5.46×10-6,2H质子9:δ=6.11×10-6,1H质子10:δ=4.73×10-6,2H由此确认所合成的化合物的结构与预期一致。 Proton 3: δ = 8.03 × 10-6,2H protic 4: δ = 8.34 × 10-6,2H protic 5: δ = 7.51 × 10-6,1H protic 6: δ = 7.78 × 10-6,1H protons 7 : δ = 8.12 × 10-6,1H protic 8: δ = 5.32 ~ 5.46 × 10-6,2H proton 9: δ = 6.11 × 10-6,1H proton 10: δ = 4.73 × 10-6,2H whereby consistent with the structure expected to confirm the synthesized compounds.

通过正交偏光显微镜对所合成的样品进行观察,常温下样品在偏光显微镜下呈现片状晶体,将样品以5℃/min的速率加热,至约125℃时样品熔解进入液晶态,视野中出现大量液滴,液滴中出现众多黑色条纹,交叉处出现十字消光现象,呈现出典型的条纹织构,并且迅速流动,表明样品目前以向列相液晶态存在。 By orthogonal polarization microscope observation of the sample synthesized sample presentation plate crystal at room temperature under a polarizing microscope, the sample is heated at a rate of 5 ℃ / min, the sample enters the liquid crystal state when melting to about 125 deg.] C, field of view appears a plurality of droplets, the droplet number of black stripes appear, at the intersection of cross-quenching phenomenon occurs, showing the typical texture of stripes, and flows rapidly, indicating that the sample currently exist nematic liquid crystalline state. 这说明4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯是一种单变热致液晶。 This indicates 4'-allyloxy-4-fluoro-4-azobenzene-carboxylic acid ester is a mono-cyanophenyl variation thermotropic liquid crystal.

以上关于液晶性质的测试结果说明4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯适合作为液晶显示器中所用的液晶复合物的理想的组成成分,适合用于TN、STN、TFT等液晶显示器所用的液晶复合材料中。 Test results for the above described properties of the liquid crystal 4'-allyloxy-4-azobenzene-carboxylic acid 4-cyano-3-fluoro-phenyl ester ideally suited as a component of liquid crystal compound used in a liquid crystal display, and liquid crystal composite material suitable for TN, STN, TFT liquid crystal displays are used.

Claims (2)

  1. 1.一种液晶化合物——4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯,其结构式为 1. A liquid crystal compound --4'- azobenzene-allyloxy-4-carboxylic acid 4-cyano-3-fluoro-phenyl ester, having the formula
  2. 2.一种液晶化合物——4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯的制备方法,其特征在于1)在pH>10的酸碱度、50~80℃的温度下,在溶液中加入3-卤代丙烯和对羟基偶氮苯羧酸,使两者发生缩合反应,生成4'-烯丙氧基-4-偶氮苯羧酸,2)缩合完毕后,以强碱在乙醇-水混合溶剂中的溶液在50~80℃条件下通过水解反应除去反应步骤1)中生成的副产物,3)以N,N-二环己基碳二亚胺为脱水剂,N,N-二甲氨基吡啶为催化剂,在0~30℃下反应,促使4'-烯丙氧基-4-偶氮苯羧酸和2-氟-4-羟基苯腈脱水缩合成4'-烯丙氧基-4-偶氮苯羧酸-3-氟-4-氰基苯酯。 A liquid crystal compound --4'- azobenzene-allyloxy-4-carboxylic acid 3-fluoro-4-cyanophenyl ester method, wherein 1) at pH> 10 pH, at a temperature of 50 ~ 80 ℃, adding propylene and 3-halo-hydroxybenzoic acid azobenzene, so that both the condensation reaction to produce 4'-allyloxy-4-carboxylic acid in solution azobenzene, 2) after the condensation is completed, the strong base in ethanol - water mixed solvent solution at 50 ~ 80 ℃ the reaction product of a) removing the generated reaction step, 3) in N, N- dicyclohexylcarbodiimide by hydrolysis carbodiimide as a dehydrating agent, N, N- dimethylaminopyridine as catalyst, the reaction at 0 ~ 30 ℃, prompting 4'-allyloxy-4-carboxylic acid azobenzene and 2-fluoro-4-hydroxy benzonitrile dehydration condensation of 4'-allyloxy-4-azobenzene-carboxylic acid 4-cyano-3-fluoro-phenyl ester.
CN 200610139011 2006-09-21 2006-09-21 Liquid crystal compound 4'-allyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof CN100410347C (en)

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CN103013535A (en) * 2012-12-28 2013-04-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN103013532A (en) * 2012-11-30 2013-04-03 浙江工业大学 Azobenzene photochromic liquid crystal compound and method for synthesizing same

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US4514045A (en) 1981-06-22 1985-04-30 Minnesota Mining And Manufacturing Company Helichromic-smectic liquid crystal compositions and display cells
JP3579727B2 (en) 1994-05-06 2004-10-20 チッソ株式会社 The liquid crystal composition
CN1261407C (en) 2002-01-25 2006-06-28 中国科学院化学研究所 Azo structure contained fluorine-aromatic diamine and preparation process and use thereof
CN1325456C (en) 2002-12-24 2007-07-11 株式会社艾迪科 Perfluoroallyloxy compound and liquid-crystal composition containing the compound
JP4581706B2 (en) 2004-01-29 2010-11-17 住友ベークライト株式会社 The positive photosensitive resin composition, the positive photosensitive resin composition to a semiconductor device and a display device using, as well as a method of manufacturing a semiconductor device and a display device

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CN103013532A (en) * 2012-11-30 2013-04-03 浙江工业大学 Azobenzene photochromic liquid crystal compound and method for synthesizing same
CN103013535A (en) * 2012-12-28 2013-04-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN103013535B (en) 2012-12-28 2014-02-26 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof

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