CN108795444A - 一种具有负介电各向异性的液晶化合物及其制备方法与应用 - Google Patents
一种具有负介电各向异性的液晶化合物及其制备方法与应用 Download PDFInfo
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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Abstract
本发明涉及一种具有负介电各向异性的液晶化合物及其制备方法与应用。本发明提供了一种具有负介电各向异性的通式Ⅰ的液晶化合物，制备方法及其应用。所述液晶化合物具有稳定的物理化学性质、合适的光学各向异性、合适的清亮点、液晶相温度范围较宽，较大的介电各向异性绝对值等特点，好的稳定性及抗UV能力，可以用于VA显示模式，如MVA、PVA、PSVA等。
Description
技术领域
本发明涉及一种具有负介电各向异性的液晶化合物及其制备方法与应用。
背景技术
负介电各向异性液晶广泛应用于DS、ECB、GH、FLC，PDLC等显示模式的液晶显示中。此类液晶可以用来调节液晶混合物的参数，以提高显示器件的性能。为更好的满足液晶显示的需求，越来越多官能团种类的负介电各向异性液晶化合物被开发，尤其是具备多种效果的负介电各向异性液晶化合物更急需开发，因此，有必要提出有效的技术方案，解决上述问题。
发明内容
本发明针对上述现有技术的不足，提供一种具有负介电各向异性的液晶化合物。所述液晶化合物具有稳定的物理化学性质、合适的光学各向异性、合适的清亮点、液晶相温度范围较宽，较大的介电各向异性绝对值。
本发明解决上述技术问题的技术方案如下：
一种具有负介电各向异性的液晶化合物，其特征在于，所述液晶化合物具有通式Ⅰ结构：
其中，R1，R2可相同，可不同；R1，R2各自独立的表示氢原子、碳原子数为1-7的烷基、碳原子数为1～6的烷氧基或碳原子数为2～6的链烯基；
表示
表示
Z1表示单键、—COO—、—CH2O—、—C2H4—、—CF2O—或—C≡C—；
m，n分别独立的表示0或1。
优选地，所述R1和R2各自独立的表示碳原子数为1-5的烷基、碳原子数为1～5的烷氧基或碳原子数为2～5的链烯基。
优选地，所述通式Ⅰ的化合物选自如下通式Ⅰ-1至Ⅰ-20中的一种：
有益效果：液晶化合物具有稳定的物理化学性质、合适的光学各向异性、合适的清亮点、液晶相温度范围较宽，较大的介电各向异性绝对值等特点，好的稳定性及抗UV能力，可以用于VA显示模式，如MVA、PVA、PSVA等。
本发明还提供一种制备具有通式Ⅰ结构的具有负介电各向异性的液晶化合物的方法，包括如下步骤：
(1)化合物a通过格氏反应，氢化反应合成化合物b；
(2)化合物b通过锂化反应,硼酸suzuki偶联反应，mitsnobu反应得具有通式Ⅰ结构的目标化合物。
本发明还提供一种液晶组合物，具备上述任一项所述的具有负介电各向异性的液晶化合物。
本发明还提供一种液晶显示器，包含上述任一项所述的液晶化合物。
具体实施方式
实施例1
液晶化合物的制备方法，如下：
机理:
1 58.6g 2,3-二三氟甲基溴苯用THF做溶剂，单质碘引发，做成格氏试剂；冷却到-20℃，将18g戊醛滴加到格氏试剂中，控制温度在-20℃，自然升至室温，搅拌2h；旋干，加入氯化铵水溶液，用EA萃取；EA相用饱和食盐水洗涤2次，干燥；加入300ml THF，30ml TFA室温搅拌12h，旋干得50.8g化合物1。
2 50.8g化合物1，0.3g钯炭在300ml乙醇中，常压氢气加氢5h。过滤，旋干得51g化合物2。
3 51g化合物2溶于300ml THF中，冷却到-78℃，将80ml丁基锂在-70℃下滴入，升温到-50℃，搅拌1h；冷却到-78℃，将28g对丙基环己酮滴入，控制温度在-50℃，自然升至室温，搅拌2h；旋干，加入氯化铵水溶液，用EA萃取；EA相用饱和食盐水洗涤2次，干燥；加入300mlTHF，30ml TFA搅拌12h，旋干得65g化合物3。
4 65g化合物3，0.3g钯炭在300ml乙醇中，常压氢气加氢5h。过滤，旋干，用乙醇在-10℃下重结晶得40g目标化合物。纯度:99.9％。
实施例2
液晶化合物的制备方法，如下：
机理:
1 42.6g化合物2溶于300mlTHF中，冷却到-78℃，将66ml丁基锂在-70℃下滴入，升温到-50℃，搅拌1h；冷却到-78℃，将37g硼酸三丁酯滴入，自然升至室温，搅拌6h；加入200ml含有40ml浓盐酸的水，搅拌0.5h，分层，得有机层化合物4。
2步骤1所得有机相中加入100ml 30％双氧水，室温搅拌2h；将THF常压蒸馏走，用DCM萃取两次，合并有机相，旋干，用乙醇重结晶，得30g化合物5。
3 34g对丙基环己烷羧酸溶入200ml盐酸甲醇溶液中，加热回流10h，旋干得40g化合物6。
4 40g化合物6，7.6g硼氢化钠，200ml无水乙醇0℃搅拌0.5h，自然升至室温，搅拌2h；用水淬灭，旋干，加入EA，用饱和食盐水洗涤3次；旋干得28g化合物7。
5 28g化合物7，22g三乙胺溶于200mlDCM中，将29g甲基磺酰氯在0℃下滴入，自然恢复到室温，搅拌8h；用2％的盐酸水溶液洗涤3次，饱和食盐水洗涤3次，干燥，旋干得37g化合物8。
6 23.4g化合物8，30g化合物5，15g碳酸钾在200ml乙腈中常温搅拌8h。旋干，加入200ml甲苯，用去离子水洗涤4次，干燥，旋干，用乙醇在-20℃下重结晶得30g目标化合物。纯度:99.9％。
实施例3
液晶化合物的制备方法，如下：
机理:
1 24g对丙基溴苯，45g碳酸钠，200ml甲苯，100ml水，0.3g四三苯基膦钯，0.5g冠醚，氮气保护下加热到60℃，将步骤4所得有机相滴入，在70℃下搅拌5h。冷却，分层，有机相用去离子水洗涤4次；干燥，旋干，用石油醚-30℃下重结晶得20g目标化合物。纯度:99.9％。
实施例4
液晶化合物的制备方法，如下：
机理:
1 21.3g对丙基苄溴，30g化合物5，15g碳酸钾在200ml乙腈中常温搅拌8h。旋干，加入200ml甲苯，用去离子水洗涤4次，干燥，旋干，用乙醇-20℃下重结晶得28g目标化合物。纯度:99.9％。
实施例5
液晶化合物的制备方法，如下：
机理:
1 51g化合物2溶于300mlTHF中，冷却到-78℃，将80ml丁基锂在-70℃下滴入，升温到-50℃，搅拌1h。冷却到-78℃，将44g丙基双环己基酮滴入，控制温度在-50℃，自然升至室温，搅拌2h。旋干，加入氯化铵水溶液，用EA萃取；EA相用饱和食盐水洗涤2次，干燥。加入300mlTHF，30ml TFA搅拌12h，旋干得78g化合物9。
2 78g化合物9，0.5g钯炭在300ml乙醇中，常压氢气加氢5h。过滤，旋干，用乙醇0℃下重结晶得50g目标化合物。Purity:99.9％。
实施例6
液晶化合物的制备方法，如下：
机理:
1 50g对戊基环己烷羧酸溶入200ml盐酸甲醇溶液中，加热回流10h，旋干得56g化合物10。
2 56g化合物10，8g硼氢化钠，200ml无水乙醇0℃搅拌0.5h，自然升至室温，搅拌2h。用水淬灭，旋干，加入EA，用饱和食盐水洗涤3次。旋干得47g化合物11。
3 47g化合物11，22g三乙胺溶于200mlDCM中，将29g甲基磺酰氯在0℃下滴入，自然恢复到室温，搅拌8h。用2％的盐酸水溶液洗涤3次，饱和食盐水洗涤3次，干燥，旋干得62g化合物12。
4 31.6g化合物12，30g化合物5，15g碳酸钾在200ml乙腈中常温搅拌8h。旋干，加入200ml甲苯，用去离子水洗涤4次，干燥，旋干，用乙醇0℃下重结晶得40g目标化合物。纯度:99.9％
实施例7
液晶化合物的制备方法，如下：
机理:
33.6g1-溴-4-(4-丙基环己基)苯，45g碳酸钠，200ml甲苯，100ml水，0.3g四三苯基膦钯，0.5g冠醚，氮气保护下加热到60℃，将步骤4所得有机相滴入，在70℃下搅拌5h。冷却，分层，有机相用去离子水洗涤4次。干燥，旋干，乙醇0℃下重结晶得30g目标化合物。纯度:99.9％。
实施例8
液晶化合物的制备方法，如下：
机理:
33.4g对溴丙基联苯，45g碳酸钠，200ml甲苯，100ml水，0.3g四三苯基膦钯，0.5g冠醚，氮气保护下加热到60℃，将步骤4所得有机相滴入，在70℃下搅拌5h。冷却，分层，有机相用去离子水洗涤4次。干燥，旋干，乙醇10℃下重结晶得28g目标化合物。纯度:99.9％。
本发明所述液晶化合物具有稳定的物理化学性质、合适的光学各向异性、合适的清亮点、液晶相温度范围较宽，较大的介电各向异性绝对值等特点，好的稳定性及抗UV能力，可以用于VA显示模式，如MVA、PVA、PSVA等。
本发明可用其他的不违背本发明的精神或主要特征的具体形式来概述。因此，无论从哪一点来看，本发明的上述实施方案都只能认为是对本发明的说明而不能限制本发明，权利要求书指出了本发明的范围，而上述的说明并未指出本发明的范围，因此，在与本发明的权利要求书相当的含义和范围内的任何改变，都应认为是包括在本发明的权利要求书的范围内。
Claims (6)
1.一种具有负介电各向异性的液晶化合物，其特征在于，所述液晶化合物具有通式Ⅰ结构：
其中，R1，R2可相同，可不同；R1，R2各自独立的表示氢原子、碳原子数为1-7的烷基、碳原子数为1～6的烷氧基或碳原子数为2～6的链烯基；
表示
表示
Z1表示单键、—COO—、—CH2O—、—C2H4—、—CF2O—或—C≡C—；
m，n分别独立的表示0或1。
2.根据权利要求1所述的具有负介电各向异性的液晶化合物，其特征在于，所述R1和R2各自独立的表示碳原子数为1-5的烷基、碳原子数为1～5的烷氧基或碳原子数为2～5的链烯基。
3.根据权利要求1所述的具有负介电各向异性的液晶化合物，其特征在于，所述通式Ⅰ的化合物选自如下通式Ⅰ-1至Ⅰ-20中的一种：
4.一种制备具有通式Ⅰ结构的具有负介电各向异性的液晶化合物的方法，其特征在于，包括如下步骤：
(1)化合物a通过格氏反应，氢化反应合成化合物b；
(2)化合物b通过锂化反应,硼酸suzuki偶联反应，mitsnobu反应得具有通式Ⅰ结构的目标化合物。
5.一种液晶组合物，其特征在于，具备权利要求1～4任一项所述的具有负介电各向异性的液晶化合物。
6.一种液晶显示器，其特征在于，包含权利要求1～4任一项所述的液晶化合物。
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