CN1743414A - 含有单氟乙撑桥键的液晶化合物及其制备方法 - Google Patents
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- 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 19
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Abstract
本发明公开了含有单氟乙撑桥键的液晶化合物及其制备方法。本发明所提供的含有单氟乙撑桥键的液晶化合物,具有式I的结构,其中,n为1-7的正整数;m为1-5的正整数。本发明液晶化合物的中心桥键上出现氟原子,制备方法简单,具有熔点低,宽液晶相温度范围和低粘度等特点,在液晶显示领域将具有广阔的应用前景。
Description
技术领域
本发明涉及液晶化合物及其制备方法,特别是涉及含有单氟乙撑桥键的液晶化合物及其制备方法。
背景技术
进入21世纪以来,薄膜晶体管(Thin Solid Film:TFT)液晶显示全面覆盖了大中小各个尺寸的显示领域,被广泛的应用于电视、便携式计算机、桌面电脑、摄像机、手机等各种终端显示器,成为平板显示的主流。随着TFT液晶显示技术的高速发展,对高性能液晶材料的要求越来越迫切,因此研制对热、化学、电、光稳定性好,电荷保持率高,粘度低,电阻率高的高性能液晶材料是TFT用液晶材料的今后的研究方向。
由于任何一种单体液晶在显示上都不可能满足所有性能要求,所以在显示上均采用由多种单体液晶按比例组成的混合液晶材料。乙烷类液晶由于其结构上的特殊性,当其作为混合液晶的某一组分存在时,能够降低混合液晶的粘度和光学各向异性,拓宽液晶相的使用温度范围,同时还具有良好的光稳定性和化学稳定性,因此是一种性能良好的液晶材料。日本Chisso公司的Yasuyuki Goto等合成了各种含有-CH2CH2-中心桥键的乙烷类液晶单体(US Patent 4797228,US Patent 4820443),Shuichi Matsui等也在乙烷类液晶单体的研究方面做了很多研究(US Patent 5468421)。
发明内容
本发明的目的是提供一种含有单氟乙撑桥键的液晶化合物及其制备方法。
本发明所提供的含有单氟乙撑桥键的液晶化合物,其结构式如式I,
其中,n为1-7的正整数;m为1-5的正整数。
具体的,上述液晶化合物为如下化合物中的一种:
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷。
该液晶化合物的这制备方法,包括如下步骤:
1)制备结构如式II的1-(4’-反式-(4”-反式-烷基环己基)己环基)-1-羟基-2-(4-烷基苯基)乙烷:将式III结构的4-烷基苯基溴甲烷先与金属镁反应生成格利雅试剂,再与式IV结构的4-反式-(4’-反式-烷基环己基)环己基甲醛进行还原反应,得到式II化合物;
其中,n为1-7的正整数;m为1-5的正整数;
2)制备式I液晶化合物:将式II化合物与式V结构的二乙基氨基三氟化硫反应,得到所述式I液晶化合物。
(C2H5)2N·SF3 (式V)
其中,步骤1)格氏反应所用溶剂为四氢呋喃,反应温度为20-30℃;还原反应所用溶剂为四氢呋喃,反应温度为-10~5℃。
步骤2)反应溶剂为二氯甲烷,反应温度为-80~-70℃。
本发明液晶化合物的中心桥键上出现氟原子,制备方法简单,具有熔点低,宽液晶相温度范围和低粘度等特点,在液晶显示领域将具有广阔的应用前景。
具体实施方式
实施例1、1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷的制备
1、制备1-(4’-反式-(4”-反式-丙环己基)环己基)-1-羟基-2-(4-乙基苯基)乙烷
往500ml三口瓶中加入19.9g(0.1mol)4-乙基苯基溴甲烷,100ml四氢呋喃,2.43g(0.1mol)金属镁和1~2粒碘,在室温下(20~30℃)引发反应后搅拌1小时制成格利雅试剂。用冰水将该溶液冷却0℃,往该溶液中缓慢滴加含有23.6g(0.1mol)4-反式-(4’-反式-丙基环己基)环己基甲醛和200ml四氢呋喃的混合溶液,滴加完毕后搅拌12个小时,得到浅黄色的混浊溶液。往此溶液中滴加50ml0.1mol的盐酸,得到黄色澄清溶液。用750ml乙醚分三次萃取该溶液,然后合并萃取液。用100ml质量浓度为2%NaHCO3水溶液洗涤该乙醚溶液两次后,用无水Na2SO4干燥乙醚溶液4小时,蒸除乙醚,得到浅黄色的固体28g。用200ml无水乙醇重结晶,得到白色固体1-(4’-反式-(4”-反式-丙环己基)环己基)-1-羟基-2-(4-乙基苯基)乙烷-(4’-反式-(4-反式-丙环己基)环己基)-1-羟基-2-(4-乙基苯基)乙烷21.5g,气相色谱纯度为99.1%,收率为60.4%。
IR:3300,2962,2920,2846,1520,1444,1425,1370,1320,1265,1223,1100,1065,1020,975,850,810,670;
MS:356(M+),355,339,296,237,220,207,132,119,117,91,83,69 55,43;
2、1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷的制备
往500ml三口瓶中加入7.2g(0.02mol)1-(4’-反式-(4”-反式-丙环己基)环己基)-1-羟基-2-(4-乙基苯基)乙烷和180ml的二氯甲烷混合溶液,然后用液氮和乙醇的混合物将溶液冷却至-70℃,搅拌条件下滴加二乙基氨基三氟化硫(DAST)和50ml二氯甲烷的溶液,保持反应温度不高于-70℃,搅拌反应10小时。升温至-45℃,加100ml饱和碳酸氢钠水溶液,升至室温。静置分液,水相用二氯甲烷萃取,合并有机相,水洗至中性,再用无水硫酸钠干燥5小时。抽滤后旋蒸,得到白色粗品4.8g,用硅胶柱分离粗品,石油醚淋洗后旋干溶液,得到白色固体3.5g,再用无水乙醇重结晶,得到白色晶体1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷2.8g,气相色谱纯度为99.5%,收率为39.1%。
DSC:Cr 38.7℃ N 160.7 ℃I
IR:2980,2920,2846,1516,1444,1429,1375,1261,1223,1097,1050,1020,972,940,854,810,687
MS:358(M+),339,253,239,220,149,132,119,103,91,83,69,55,43,41
粘度(η):20mm2·s
表明所得化合物结构正确。
其DSC和粘度数据表明,该化合物是一种性能优良的液晶化合物。
采用与上相同的方法将4-烷基苯基溴甲烷与金属镁反应生成格利雅试剂,再与4-反式-(4’-反式-烷基环己基)环己基甲醛进行还原反应制得1-(4’-反式-(4”-反式-烷基环己基)环己基)-1-羟基-2-(4-烷基基苯基)乙烷。再将1-(4’-反式-(4”-反式-烷基环己基)环己基)-1-羟基-2-(4-烷基基苯基)乙烷与二乙基氨基三氟化硫(DAST)进行反应都可以得到以下化合物,这些化合物同样均是性能优良的液晶化合物:
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷。
Claims (5)
2、根据权利要求1所述的液晶化合物,其特征在于:所述化合物为如下化合物中的一种:
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-甲基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-乙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丙基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-丁基苯基)乙烷,
1-(4’-反式-(4”-反式-甲基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-乙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丙基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-丁基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-戊基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-己基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷,
1-(4’-反式-(4”-反式-庚基环己基)环己基)-1-氟-2-(4-戊基苯基)乙烷。
4、根据权利要求3所述的制备方法,其特征在于:步骤1)格氏反应所用溶剂为四氢呋喃,反应温度为20-30℃;还原反应所用溶剂为四氢呋喃,反应温度为-10~5℃。
5、根据权利要求3所述的制备方法,其特征在于:步骤2)反应溶剂为二氯甲烷,反应温度为-80~-70℃。
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