CN107880900B - 含有2,3,4-三取代苯的液晶化合物及其组合物 - Google Patents

含有2,3,4-三取代苯的液晶化合物及其组合物 Download PDF

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CN107880900B
CN107880900B CN201610862010.5A CN201610862010A CN107880900B CN 107880900 B CN107880900 B CN 107880900B CN 201610862010 A CN201610862010 A CN 201610862010A CN 107880900 B CN107880900 B CN 107880900B
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carbon atoms
liquid crystal
fluorine
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substituted
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CN107880900A (zh
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员国良
崔红梅
王明霞
康素敏
张永涛
陈勇
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Priority to TW106124197A priority patent/TW201829748A/zh
Priority to TW109136208A priority patent/TWI755897B/zh
Priority to US15/714,234 priority patent/US10767113B2/en
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Abstract

本发明提供了一种含有2,3,4‑三取代苯的液晶化合物、一种液晶组合物及包含该液晶化合物、液晶组合物的液晶显示元件或液晶显示器，该液晶组合物具有较低的粘度，可以实现快速响应，同时具有适中的介电各向异性Δε、适中的光学各向异性Δn、高的对热和光的稳定性。包含该液晶组合物的液晶显示元件或液晶显示器具有较宽的向列相温度范围、合适的双折射率各向异性、非常高的电阻率、良好的抗紫外线性能、高电荷保持率以及低蒸汽压等性能，尤其是该液晶化合物、液晶组合物具有光穿透率高的优势。

Description

含有2,3,4-三取代苯的液晶化合物及其组合物
技术领域
本发明涉及液晶显示领域，具体涉及一种含有2,3,4-三取代苯的液晶化合物、一种液晶组合物及包含该液晶化合物、组合物的液晶显示元件或液晶显示器。
背景技术
目前，液晶化合物的应用范围拓展的越来越广，其可应用于多种类型的显示器、电光器件、传感器等中。用于上述显示领域的液晶化合物的种类繁多，其中向列相液晶应用最为广泛。向列相液晶已经应用在无源TN、STN矩阵显示器和具有TFT有源矩阵的系统中。
对于薄膜晶体管技术(TFT-LCD)应用领域，近年来市场虽然已经非常巨大，技术也逐渐成熟，但人们对显示技术的要求也在不断的提高，尤其是在实现快速响应，降低驱动电压以降低功耗等方面。液晶材料作为液晶显示器重要的光电子材料之一，对改善液晶显示器的性能发挥重要的作用。
作为液晶材料，需要具有良好的化学和热稳定性以及对电场和电磁辐射的稳定性。而作为薄膜晶体管技术(TFT-LCD)用液晶材料，不仅需要具有如上稳定性外，还应具有较宽的向列相温度范围、合适的双折射率各向异性、非常高的电阻率、良好的抗紫外线性能、高电荷保持率以及低蒸汽压等性能。
对于动态画面显示应用，消除显示画面残影和拖尾，要求液晶具有很快的响应速度，因此要求液晶具有较低的旋转粘度γ1；另外，对于便携式设备，为了降低设备能耗，希望液晶的驱动电压尽可能低；而对于电视等用途的显示器来说，对于液晶的驱动电压要求不是那么的低。
液晶化合物的粘度，尤其是旋转粘度γ1直接影响液晶加电后的响应时间，不管是上升时间(ton)还是下降时间(toff)，都与液晶的旋转粘度γ1成正比关系，上升时间(ton)由于与液晶盒和驱动电压有关，可以通过加大驱动电压的方法与降低液晶盒盒厚来调节；而下降时间(toff)与驱动电压无关，主要是与液晶的弹性常数与液晶盒盒厚有关，盒厚的下降会降低下降时间(toff)，而不同显示模式下，液晶分子的运动方式不一样，TN、IPS、VA三种模式分别与平均弹性常数K、扭曲弹性常数、弯曲弹性常数成反比关系。
依照液晶连续体理论，各种不同的液晶在外力(电场、磁场)作用下发生形变后，会通过分子间的相互作用，会“回弹”回原来的形状；同样的，液晶也是由于分子间的相互作用力形成“粘度”。液晶分子的微小变化，会使液晶的常规参数性能发生明显的变化，这些变化有的是有一定规律的，有的似乎不易找到规律，对于液晶分子间的相互作用也会产生明显的影响，这些影响非常微妙，至今也没有形成很完善的理论解释。
液晶的粘度与液晶分子结构有关，研究不同液晶分子形成的液晶体系的粘度与液晶分子结构之间的关系是液晶配方工程师的重要任务之一。
液晶面板能耗高的原因是只有大约5％左右的背光才能够穿透显示器件，而被人眼捕获，绝大部分光是被“浪费”了的。如果能够开发出光穿透率高的液晶，即能够降低背光强度，从而实现节省能耗的目的，延长设备的使用时间。
发明内容
本发明的目的在于提供一种含有2,3,4-三取代苯的液晶化合物、一种液晶组合物及包含该液晶化合物、液晶组合物的液晶显示元件或液晶显示器，该液晶组合物具有较低的粘度，可以实现快速响应，同时具有适中的介电各向异性Δε、适中的光学各向异性Δn、高的对热和光的稳定性。包含该液晶组合物的液晶显示元件或液晶显示器具有较宽的向列相温度范围、合适的双折射率各向异性、非常高的电阻率、良好的抗紫外线性能、高电荷保持率以及低蒸汽压等性能，尤其是该液晶化合物、液晶组合物具有光穿透率高的优势。
为了实现上述有益技术效果，本发明提供了一种液晶组合物，其特征在于包含有一种或多种式Ⅰ所示化合物，以及一种或多种式Ⅱ化合物，且所述液晶组合物中至少还包含一种或两种式Ⅱ中所含式Ⅱ-B的化合物，
Figure BDA0001123431060000021
Figure BDA0001123431060000031
其中，R0、R1、R3各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10 的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基,且R0、R1、 R3所示基团中任意一个或多个不相连的CH2可以被环戊基、环丁基、环丙基或-O-替代；
Y表示乙基或乙烯基；
R2表示F、OCF3、OCHF2、OCH2F；
Figure BDA0001123431060000032
各自独立地表示
Figure BDA0001123431060000033
Figure BDA0001123431060000034
或任意氟代苯的其中一种；
m、n各自独立地表示1或2。
式Ⅰ所示化合物，m、n都表示1时，为三环化合物，具有较好的溶解性，在液晶中可以添加较多的份数，比如10％，同时具有较低的粘度；m、n其中一个表示2时，为四环化合物，具有很高的清亮点，对于提升液晶的清亮点非常有帮助，但是溶解性较差，添加量一般较小，比如5％；m、n都表示2时，具有非常高的清亮点，溶解性进一步下降，比如1％。环数量的不同，液晶的性能会表现出一些差异，但是与式Ⅱ-B搭配使用都具有提升穿透率的性能，同时具有很低的粘度等性能，尤其适用于IPS显示模式。
所述一种或多种式Ⅰ所示化合物优选为式Ⅰ1-Ⅰ24所示化合物中的一种或多种化合物；所述式Ⅱ所示化合物优选包含式Ⅱ1至Ⅱ10化合物的一种或多种化合物；所述一种或两种式Ⅱ-B所示化合物优选为式Ⅱ-B-1至Ⅱ-B-2所示化合物中的一种或两种化合物，
Figure BDA0001123431060000035
Figure BDA0001123431060000041
Figure BDA0001123431060000051
Figure BDA0001123431060000061
其中，R11各自独立地表示碳原子数为1-6的烷基、原子数为2-6的烯基。
所述液晶组合物式Ⅰ所示化合物质量百分比含量优选为0.5-50％，式Ⅱ-B 质量百分比含量为优选为5-65％，一种或多种除Ⅱ-B之外的式Ⅱ所示化合物质量百分比含量优选为0-30％。
本发明所提供的液晶组合物可以为正性液晶组合物，所述液晶组合物还可以包含一种或多种式Ⅲ所示化合物
Figure BDA0001123431060000062
其中，R4表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为 2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基；且R4中任一个或多个CH2可以被环戊基、环丁基或环丙基替代；
Figure BDA0001123431060000071
各自独立地表示：
Figure BDA0001123431060000072
中的一种或两种；
m表示1或2；
Z1、Z2各自独立地表示单键、-CF2O-、-CH2CH2-或-CH2O-；
Y2表示F、氟取代的碳原子数为1-5的烷基、氟取代的碳原子数为1-5的烷氧基、氟取代的碳原子数为2-5的链烯基或氟取代的碳原子数为3-8的链烯氧基。
所述一种或多种式Ⅲ所示化合物优选为Ⅲ1-Ⅲ26化合物
Figure BDA0001123431060000073
Figure BDA0001123431060000081
Figure BDA0001123431060000091
Figure BDA0001123431060000101
其中，X1、X2各自独立的表示H或F，但在同一分子式中不能同时为F，也不能同时为H；
R4各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8 的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R4所示基团中任一个 CH2可以被环戊基、环丁基或环丙基替代；
(F)各自独立地表示H或F；
Y2各自独立地表示F、氟取代的碳原子数为1-5的烷基、氟取代的碳原子数为1-5的烷氧基、氟取代的碳原子数为2-5的链烯基、氟取代的碳原子数为 3-8的链烯氧基。
本发明所提供的液晶组合物，也可以为负性液晶组合物，所述液晶组合物还可以包含一种或多种式Ⅳ所示的化合物
Figure BDA0001123431060000102
其中，R5、R6各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R5、R6所示基团中任一个CH2可以被环戊基、环丁基或环丙基替代；
Z3、Z4各自独立地表示单键、-CH2CH2-或-CH2O-；
Figure BDA0001123431060000111
各自独立地表示
Figure BDA0001123431060000112
Figure BDA0001123431060000115
中的一种或多种；
m表示1或2；
n表示0，1或2。
所述一种或多种式Ⅳ所示的化合物可以为式Ⅳ1-Ⅳ11所示化合物中的一种或多种
Figure BDA0001123431060000114
Figure BDA0001123431060000121
其中，R5、R6各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R5、R6所示基团中任一个CH2可以被环戊基、环丁基或环丙基替代。
所述正性或负性液晶组合物还可以包含一种或多种式Ⅴ所示的化合物
Figure BDA0001123431060000122
其中，R7、R8各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R7、R8所示基团中任一个CH2可以被环戊基、环丁基或环丙基替代。
本发明所提供的液晶组合物，还可以包含一种或多种式Ⅵ化合物
Figure BDA0001123431060000123
其中，R91表示碳原子数为1-5的烷基或碳原子数为2-5的链烯基；
R92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；
Figure BDA0001123431060000131
表示
Figure BDA0001123431060000132
本发明还涉及一种式Ⅰ-A所示液晶化合物
Figure BDA0001123431060000133
其中，R1表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为 2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R1所示基团中任意一个或多个不相连的CH2可以被环戊基、环丁基、环丙基或-O-替代；
Y表示乙基或乙烯基；
m、n各自独立的表示1或2；
Figure BDA0001123431060000134
表示
Figure BDA0001123431060000135
Figure BDA0001123431060000136
中的一种或两种
条件是，当m+n＝2，
Figure BDA0001123431060000137
表示
Figure BDA0001123431060000138
且R2表示F时，
Figure BDA0001123431060000139
不能表示
Figure BDA00011234310600001310
式Ⅰ-A所示液晶化合物，优选为式Ⅰ2-Ⅰ4、Ⅰ6-Ⅰ24所示化合物
Figure BDA00011234310600001311
Figure BDA0001123431060000141
Figure BDA0001123431060000151
本发明Ⅰ-A化合物具有低粘度、较宽的折射率范围、中等的正的介电各向异性、尤其是同时具有较大的垂直方向的折射率，而且对光和热稳定，是一类通用的提升垂直方向介电各向异性的液晶化合物，而不会给平行方向介电各向异性给出太大的提高。
其中，R11各自独立地表示碳原子数为1-6的烷基或原子数为2-6的烯基。
本发明还涉及一种包含权利要求1-9中任一所述液晶化合物、液晶组合物的液晶显示元件或液晶显示器，所述液晶显示元件或液晶显示器为有源矩阵显示元件或显示器，或者无源矩阵。
合成方法：
Figure BDA0001123431060000161
a:甲苯乙醇水Na2CO3Pd(PPh3)4
本发明液晶化合物具有合成简便，成本低；介电适中，尤其是具有较大的垂直、平行介电；粘度低；较为广泛的折射率；可以使用于各类液晶显示模式。
本发明所提供的液晶化合物、液晶组合物中还可以加入各种功能的掺杂剂，掺杂剂含量优选0.01-1％之间，这些掺杂剂主要是抗氧化剂、紫外线吸收剂、手性剂。
抗氧化剂、紫外线吸收剂优选：
Figure BDA0001123431060000162
S表示1-10的整数。
手性剂优选(左旋或右旋)：
Figure BDA0001123431060000163
Figure BDA0001123431060000171
该液晶组合物具有较低的粘度，可以实现快速响应，同时具有适中的介电各向异性Δε、适中的光学各向异性Δn、高的对热和光的稳定性。包含该液晶组合物的液晶显示元件或液晶显示器具有较宽的向列相温度范围、合适的双折射率各向异性、非常高的电阻率、良好的抗紫外线性能、高电荷保持率以及低蒸汽压等性能，尤其是该液晶化合物、液晶组合物具有光穿透率高的优势。
具体实施方式
下面结合具体实施例对本发明作进一步阐述，但本发明并不限于以下实施例。所述方法如无特别说明均为常规方法。所述原材料如无特别说明均能从公开商业途径而得。
反应过程一般通过TLC监控反应的进程，反应结束的后处理一般是水洗、提取、合并有机相后干燥、减压下蒸除溶剂，以及重结晶、柱层析，本领域的技术人员都能够按照下面的描述来实现本发明。
本说明书中的百分比为质量百分比，温度为摄氏度(℃)，其他符号的具体意义及测试条件如下：
Cp表示液晶清亮点(℃)，DSC定量法测试；
S-N表示液晶的晶态到向列相的熔点(℃)；
Δn表示光学各向异性，no为寻常光的折射率，ne为非寻常光的折射率，测试条件为25±2℃，589nm，阿贝折射仪测试；
Δε表示介电各向异性，Δε＝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±0.5℃，20微米平行盒， INSTEC:ALCT-IR1测试；
γ1表示旋转粘度(mPa·s),测试条件为25±0.5℃，20微米平行盒， INSTEC:ALCT-IR1测试；
ρ表示电阻率(Ω·cm)，测试条件为25±2℃，测试仪器为TOYO SR6517高阻仪和LE-21液体电极。
VHR表示电压保持率(％)，测试条件为20±2℃、电压为±5V、脉冲宽度为10ms、电压保持时间16.7ms。测试设备为TOYO Model6254液晶性能综合测试仪。
τ表示响应时间(ms)，的测试仪器为DMS-501，测试条件为25±0.5℃，测试盒为3.3微米IPS测试盒，电极间距和电极宽度均为10微米，摩擦方向与电极夹角为10°。
T(％)表示透过率，T(％)＝100％*亮态(Vop)亮度/光源亮度，测试设备DMS501，测试条件为25±0.5℃，测试盒为3.3微米IPS测试盒，电极间距和电极宽度均为10微米，摩擦方向与电极夹角为10°
本发明申请实施例液晶单体结构用代码表示，液晶环结构、端基、连接基团的代码表示方法见下表(一)、表(二)
表(一)：环结构的对应代码
Figure BDA0001123431060000181
Figure BDA0001123431060000191
表(二)：端基与链接基团的对应代码
Figure BDA0001123431060000192
Figure BDA0001123431060000201
举例：
Figure BDA0001123431060000202
C(5)CCV1
Figure BDA0001123431060000203
3B B(3F)B(3F,5F)CF2OB(3F,4F,5F)
实施例1：
Figure BDA0001123431060000204
的合成
Figure BDA0001123431060000205
1000ml三口瓶中投入0.2mol丙基联苯硼酸，0.21mol 2,3,4-三氟溴苯， 300ml甲苯，300ml乙醇，200ml水，0.24mol碳酸钠，1g四三苯基膦钯，加热回流反应5小时，常规处理：石油醚溶解过硅胶柱，无水乙醇重结晶得到白色晶体49.4g，收率76％，Gc：99.91％。
Δn[589nm,25℃]：0.222
Cp：106℃
Δε[1KHz,25℃]：4.3
类似的合成处理方式，可以得到以下化合物：
Figure BDA0001123431060000211
Δn[589nm,25℃]：0.332
Cp：229℃
Δε[1KHz,25℃]：6.9
Figure BDA0001123431060000212
Δn[589nm,25℃]：0.250
Cp：241℃
Δε[1KHz,25℃]：6.8
Figure BDA0001123431060000213
Δn[589nm,25℃]：0.091
Cp：56℃
Δε[1KHz,25℃]：15
Figure BDA0001123431060000214
Δn[589nm,25℃]：0.340
Cp：110℃
Δε[1KHz,25℃]：9.3
Figure BDA0001123431060000215
Δn[589nm,25℃]：0.242
Cp：119℃
Δε[1KHz,25℃]：7.3
实施例2
Figure BDA0001123431060000221
实施例3
Figure BDA0001123431060000222
Figure BDA0001123431060000231
实施例4
Figure BDA0001123431060000232
Figure BDA0001123431060000241
对比例1
将实施例4式I化合物3CBB(2F,3F,4F)替换为常见的3CBB(3F,4F,5F)； 3BBB(2F,3F,4F)替换为常见的3BBB(3F,4F,5F)；3CCB(2F,3F,4F)替换为常见的3CCB(3F,4F,5F)，得到对比例1组合物，ε⊥从3.8降低为3.1，
测试其透过率：对比例1组合物透过率较实施例4降低8％。
实施例5
Figure BDA0001123431060000242
Figure BDA0001123431060000251
实施例6
Figure BDA0001123431060000252
实施例7
Figure BDA0001123431060000261
本发明液晶化合物具有较低的粘度，较好的对光和热的稳定性，适合于调节快速响应的，具有高透过率的液晶化合物。
本发明液晶组合物具有较低的粘度，较好的对光和热的稳定性，较宽的折射率，较宽的向列相温度范围，具有调节快速响应、高透过率的优良特性，尤其是适合用于IPS模式。

Claims (4)

1.一种液晶组合物，其特征在于所述液晶组合物为正性液晶组合物，包含有一种或多种式Ⅰ8所示化合物，以及一种或多种式Ⅱ化合物，还包含一种或多种式Ⅲ所示化合物，且所述液晶组合物中至少还包含一种或两种式Ⅱ中所含式Ⅱ-B的化合物，
Figure FDA0002791822470000011
其中，R11表示碳原子数为1-6的烷基或原子数为2-6的烯基；R0、R3各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基,且R0、R3所示基团中任意一个或多个不相连的CH2可以被环戊基、环丁基、环丙基或-O-替代；
Y表示乙基或乙烯基；
R4表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基；且R4所示基团中任一个或多个CH2可以被环戊基、环丁基或环丙基替代；
Figure FDA0002791822470000021
各自独立地表示：
Figure FDA0002791822470000022
m表示1或2；
Z1、Z2各自独立地表示单键、-CF2O-、-CH2CH2-或-CH2O-；
Y2表示F、氟取代的碳原子数为1-5的烷基、氟取代的碳原子数为1-5的烷氧基、氟取代的碳原子数为2-5的链烯基或氟取代的碳原子数为3-8的链烯氧基；
所述液晶组合物中式Ⅰ8所示化合物总质量百分比含量为5-14％，式Ⅱ-B所示化合物总质量百分比含量为35-50％，除式Ⅱ-B所示化合物之外的式Ⅱ所示化合物总质量百分比含量为9-10％，式Ⅲ所示化合物总质量百分比含量为11-20％。
2.根据权利要求1所述的液晶组合物，其特征在于，所述一种或多种式Ⅱ所示化合物包含式Ⅱ- 1至Ⅱ- 10化合物的一种或多种化合物；所述一种或两种式Ⅱ-B所示化合物为式Ⅱ-B-1至Ⅱ-B-2所示化合物中的一种或两种化合物，
Figure FDA0002791822470000023
Figure FDA0002791822470000031
3.根据权利要求1或2所述的液晶组合物，其特征在于，所述一种或多种式Ⅲ所示化合物为式Ⅲ1-Ⅲ26所示化合物中的一种或多种
Figure FDA0002791822470000032
Figure FDA0002791822470000041
Figure FDA0002791822470000051
Figure FDA0002791822470000061
其中，X1、X2各自独立地表示H或F，但在同一分子式中不能同时为F，也不能同时为H；
R4各自独立地表示碳原子数为1-10的烷基、氟取代的碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、氟取代的碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基、氟取代的碳原子数为2-10的链烯基、碳原子数为3-8的链烯氧基或氟取代的碳原子数为3-8的链烯氧基，且R4所示基团中任一个CH2可以被环戊基、环丁基或环丙基替代；
(F)各自独立地表示H或F。
4.一种包含权利要求1-3中任一所述液晶组合物的液晶显示元件或液晶显示器，其特征在于，所述液晶显示元件或液晶显示器为有源矩阵显示元件或显示器，或者无源矩阵。
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