CN107090299B - 一种含甲基取代基多氟取代化合物的液晶组合物及其应用 - Google Patents

一种含甲基取代基多氟取代化合物的液晶组合物及其应用 Download PDF

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CN107090299B
CN107090299B CN201710397961.4A CN201710397961A CN107090299B CN 107090299 B CN107090299 B CN 107090299B CN 201710397961 A CN201710397961 A CN 201710397961A CN 107090299 B CN107090299 B CN 107090299B
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史子谦
丰佩川
尹环
于涛
董向波
孙燕
付博
房凤梅
马峰
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Yantai Xianhua Technology Group Co ltd
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Abstract

本发明涉及一种含甲基取代基多氟取代化合物的液晶组合物，包括一种或多种通式Ⅰ所表示的化合物：

Description

一种含甲基取代基多氟取代化合物的液晶组合物及其应用
技术领域
本发明涉及一种液晶组合物，尤其涉及一种含甲基取代基多氟取代化合物的液晶组合物，属于液晶显示材料技术领域。
背景技术
液晶材料是实现液晶显示的关键原材料，从全球范围来看，用于TFT-LCD的混合液晶材料被德国Merck公司和日本Chisso公司所垄断，我国液晶材料产业的特点是TN(扭曲向列)、STN(超扭曲向列)较强而TFT很弱，液晶单体、中间体较强而混合液晶较弱。对下游厂商而言，液晶面板生产所需要的都是混合液晶材料，而TFT-LCD在液晶显示器领域也早已占据了主导地位，因此，TFT混合液晶的国产化是平板显示产业提高国内配套能力的重要环节。
液晶材料经过30多年的发展，目前已经合成了1万多种液晶单体，其中常用的液晶显示材料有上千种，按液晶分子的中心桥键和环的特征进行分类，主要有联苯液晶、苯基环己烷液晶、酯类液晶、炔类液晶、二氟甲氧桥类液晶、乙烷类及杂环类等。
能够用到TFT-LCD中的液晶材料除了要求物理参数与器件相匹配，如介电各向异性，折射率各向异性，弹性常数，另外还要求高稳定性，包括紫外光稳定性，高温稳定性与化学稳定性等。能够有高的稳定性的液晶材料，极性基团只能是F取代的液晶。由于单一的液晶材料不可能达到各方面性能都优异，所以开发混合液晶材料，用不同结构的单晶进行混合后，达到各方面指标尽可能优异。
发明内容
本发明针对现有单一液晶材料性质上存在的不足，提供一种含甲基取代基多氟取代化合物的液晶组合物及其应用。
本发明解决上述技术问题的技术方案如下：
一种含甲基取代基多氟取代化合物的液晶组合物，其特征在于，包括一种或多种通式Ⅰ所表示的化合物：
其中，R表示碳原子数为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、碳原子数为3-5的烯氧基、碳原子数为1-7的烷基中一个或多个氢被氟取代后所形成的基团、碳原子数为1-6的烷氧基中一个或多个氢被氟取代后所形成的基团、碳原子数为3-5的烯氧基中一个或多个氢被氟取代后所形成的基团中的任意一种；
L1，L2，L3各自独立的表示H或F；
X0表示F、Cl、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为2-6的烯烃基、碳原子数为2-6的卤代烯烃基、碳原子数为1-6的卤代烷氧基或碳原子数为2-6的卤代烯氧基中的任意一种；
独立的表示下列基团中的一种或多种：
Figure BDA0001308965350000023
m表示1、2。
进一步，所述具有通式Ⅰ的化合物的结构式如下：
Figure BDA0001308965350000041
Figure BDA0001308965350000061
进一步，还包括如通式Ⅱ～Ⅳ所表示的化合物：
Figure BDA0001308965350000062
通式Ⅱ-Ⅳ中，R1-R4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、碳原子数为3-5的烯氧基、碳原子数为1-7的烷基中一个或多个氢被氟取代后所形成的基团、碳原子数为1-6的烷氧基中一个或多个氢被氟取代后所形成的基团、碳原子数为3-5的烯氧基中一个或多个氢被氟取代后所形成的基团中的任意一种；
L1-L9各自独立的表示H或F；
X1、X2表示F、Cl、碳原子数为1-6的烷基、碳原子数为1-6的卤代烷基、碳原子数为1-6的卤代烷氧基、碳原子数为2-6的烯烃基、碳原子数为2-6的卤代烯烃基、碳原子数为2-6的卤代烯氧基中的任意一种；
Figure BDA0001308965350000072
各自独立的表示以下基团中的任意一种或多种：
Figure BDA0001308965350000073
Z1表示单键、-CH2-、-CH2-CH2-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-中的一种；
a、b、c、d、e、f、g表示0、1或2。
进一步，所述具有通式Ⅱ的化合物结构式如下：
Figure BDA0001308965350000074
Figure BDA0001308965350000081
其中，R1、R2独立的表示H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、碳原子数为3～5的烯氧基中的任意一种。
进一步，所述具有通式Ⅲ的化合物结构式如下：
Figure BDA0001308965350000101
Figure BDA0001308965350000111
其中，R3表示H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、碳原子数为3～5的烯氧基中的任意一种。
进一步，所述具有通式Ⅳ的化合物结构式如下：
Figure BDA0001308965350000112
Figure BDA0001308965350000121
Figure BDA0001308965350000131
其中，R4表示H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、碳原子数为3～5的烯氧基中的任意一种。
进一步，按重量分数计，一种或多种具有通式Ⅰ的化合物含量为1～40％，一种或多种具有通式Ⅱ的化合物含量为1～70％，一种或多种具有通式Ⅲ的化合物为1～70％，一种或多种具有通式Ⅳ的化合物为1～50％。
本发明的有益效果是：
本发明得到的液晶组合物具有非常宽的工作温度，较低的阈值电压，高的电阻率及电压保持率，化学稳定性强，良好的UV性能，紫外前后都具有高的电荷保持率，离子浓度在紫外光照射后变化较小。因此适用于TN、IPS、FFS等模式的TFT液晶显示屏。
本发明还要求保护含有上述液晶组合物的电光学液晶显示器及上述液晶组合物在液晶显示领域的应用。
本发明的液晶组合物可采用常规方法将两种或多种液晶化合物混合进行生产，如在高温下混合不同组分并彼此溶解的方法制备，其中，将液晶组合物溶解在用于该化合物的溶剂中并混合，然后在减压下蒸馏出该溶剂；或者本发明的液晶组合物可按照常规的方法制备，如将其中含量较小的组分在较高的温度下溶解在含量较大的主要组分中，或将各所属组分在有机溶剂中溶解，如丙酮、氯仿或甲醇等，然后将溶液混合后去除溶剂后得到。
具体实施方式
以下结合实例对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
实施例中所得的液晶组合物采用业内普遍使用的热溶解或震荡混合方法，首先用天平按重量百分比称量液晶化合物，其中称量加入顺序无特定要求，通常以液晶化合物熔点由高到低的顺序依次称量混合，在60℃恒温下加热搅拌或在震荡机中震荡使得各组分熔解均匀，再经吸附、微滤膜微滤滤、最后封装即得目标样品。
实施例中的百分比为重量百分比，温度为摄氏度(℃)。如无其他说明，其他符号的具体意义及测试条件如下：
Cp(℃)表示液晶的清亮点。
S-N表示液晶的晶态到向列相的熔点(℃)。
△n为光学各向异性，no为寻常光的折射率，ne为非寻常光的折射率，测试条件为，589nm波长，25℃。测量仪器：阿贝折射仪
△ε为介电各向异性，△ε＝ε∥-ε⊥，其中，ε∥为平行于分子轴的介电常数，ε⊥为垂直于分子轴的介电常数，测试条件为25℃；测量仪器：INSTEC:ALCT-IR1；20微米平行盒，未添加手性剂。
γ1：旋转粘度(mPa·s),测试条件为25±0.2℃。
测量仪器：INSTEC:ALCT-IR1；20微米平行盒，未添加手性剂。
实施例1：
液晶组合物的配方如下：
Figure BDA0001308965350000151
Figure BDA0001308965350000161
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>
数值 ≤-40 88 0.110 1.598 5.0 3.3 63
实施例2：
液晶组合物的配方如下：
Figure BDA0001308965350000162
Figure BDA0001308965350000171
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>
数值 ≤-30 100 0.110 1.586 7.6 3.4 105
实施例3：
液晶组合物的配方如下：
Figure BDA0001308965350000172
Figure BDA0001308965350000181
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>
数值 ≤-40 93 0.117 1.598 8.5 3.6 70
实施例4：
Figure BDA0001308965350000182
Figure BDA0001308965350000191
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>
数值 ≤-40 88 0.120 1.601 12.5 3.8 63
实施例5：
液晶组合物的配方如下：
Figure BDA0001308965350000192
Figure BDA0001308965350000201
上述液晶组合物的性能参数测试结果如下：
Figure BDA0001308965350000202
实施例6：
Figure BDA0001308965350000212
Figure BDA0001308965350000221
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>
数值 ≤-40 96 0.101 1.599 8.9 3.5 78
实施例7：
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>(mpa.s)
数值 ≤-40 98 0.110 1.605 15.9 3.5 85
实施例8：
液晶组合物的配方如下：
Figure BDA0001308965350000232
Figure BDA0001308965350000241
上述液晶组合物的性能参数测试结果如下：
项目 S-N(℃) Cp(℃) △n ne △ε ε⊥ γ<sub>1</sub>(mpa.s)
数值 ≤-40 92 0.100 1.597 8.6 3.4 92
以上八个实施例所得的液晶组合物，均具有很好的低温稳定性，低旋转粘度，在低温区域维持快的响应时间，可拓宽TN，IPS或者FFS液晶模式的使用温度，并且具有较快的响应时间和较宽的视角范围，非常适合用于TN，IPS和FFS模式操作的显示器。
本发明所提供的液晶组合物具有降低阈值电压与响应时间的效果，因此本发明所提供的液晶介质是用于制备快速响应、低的旋转粘度TFT液晶显示器的理想的液晶材料。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (3)

1.一种含甲基取代基多氟取代化合物的液晶组合物，其特征在于，由以下重量分数的组分组成：
Figure FDA0002269128390000011
其中，R表示碳原子数为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、碳原子数为3-5的烯氧基、碳原子数为1-7的烷基中一个或多个氢被氟取代后所形成的基团、碳原子数为1-6的烷氧基中一个或多个氢被氟取代后所形成的基团、碳原子数为3-5的烯氧基中一个或多个氢被氟取代后所形成的基团中的任意一种。
2.一种电光学液晶显示器，其特征在于，包括如权利要求1所述的液晶组合物。
3.一种权利要求1所述的液晶组合物在液晶显示领域的应用。
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