CN107459993B - 一种稳定剂及包含该稳定剂的液晶组合物 - Google Patents
一种稳定剂及包含该稳定剂的液晶组合物 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及液晶显示领域,具体涉及一种新型稳定剂,及包含此种稳定剂的液晶组合物及包含该液晶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***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。
目前,液晶显示应用的环境也逐渐多样化,除了液晶电视成为主流外,车载显示、手提电脑、Pad、手机等等,也逐渐占领人们的生活。此类移动设备使用环境复杂多变,就要求液晶材料具有高的热稳定性、高的光稳定性、很好的化学稳定性,对温度变化不敏感。
单纯的依靠材料本身已经不能满足如此苛刻的使用条件。人们很早就将稳定剂引入到了液晶材料当中,比如在专利DE19539141A1中引入的位阻酚稳定剂,TW201229217A公布的位阻胺稳定剂。
在为液晶材料带来稳定性提升的同时,还要求,不能过多的破坏或降低液晶材料本身的光学性能。不能失去了液晶材料本身所要求的适中的介电各向异性Δε、适中的光学各向异性Δn、具有较低的旋转粘度γ1、具有较高的弹性常数K值,可以实现快速响应。
发明内容
针对液晶材料对稳定剂越来越多的要求,我们开发了式Ⅰ所示新型稳定剂,不仅能提高液晶材料热和光的稳定性,还具有较高的清亮点,较好的低温互溶性,能给混合液晶材料带来更为优异的液晶性能,本发明的目的还在于提供一种液晶组合物及包含该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。
为了实现上述有益技术效果,本发明提供了一种式Ⅰ所示稳定剂:
其中,M表示环戊基、环丁基或环丙基;
Z1、Z2各自独立地表示单键、-CH2-、-CH2CH2-、-O-、-CH2O-、-OCH2-或-COO-;
n表示0、1或2。
式Ⅰ所示稳定剂,优选自如下结构:
其中,M代表环戊基、环丁基或环丙基;
Z1、Z2各自独立地表示单键、-CH2-、-CH2CH2-、-O-、-CH2O-、-OCH2-或-COO-。
式Ⅰ-a所示稳定剂进一步优选如下结构:
式Ⅰ-b所示稳定剂,进一步优选自如下结构:
上述结构除了提供了优异的稳定液晶可靠性的作用外,还具有优异的液晶性能,较高的清亮点,较低的粘度。在添加上述稳定剂后,液晶本身光学性能不会变差。
式Ⅰ-c所示稳定剂,进一步优选自如下结构:
本发明还提供了一种新型液晶组合物,本发明所提供的液晶组合物包含一种或多种如前所述的稳定剂。
本发明所提供的液晶组合物还可以包含式Ⅱ1至Ⅱ14化合物的一种或多种化合物;
其中,R0、R0’、R1、R1’、R2、R2’、R3、R3’各自独立地表示碳原子数为1-10的烷基、碳原子数为2-10的烯基或碳原子数为1-10的烷氧基,其中任意的-CH2-能被-O-取代,任意的氢能被F取代;
(F)各自独立地表示H或F。
本发明所提供的液晶组合物,具备高K值,低粘度,高清亮点,合适的折射率各向异性,特别适用于TFT液晶显示,特别是,由于其特别优越的可靠性,在高端IPS-TFT,VA-TFT,PSVA-TFT液晶中具有很好的应用价值。
作为优选方案,所述液晶组合物中式Ⅰ所示化合物总质量百分比含量优选为0.001-5%;式Ⅱ-1至Ⅱ-10所示化合物总质量百分比含量优选为1-60%;Ⅱ-11至Ⅱ-14所示化合物质量百分比含量优选为0-30%,进一步优选为1-30%;
作为优选,R0、R2各自独立地表示碳原子数为1-5的烷基或碳原子数为2-5的烯基,R1,R3各自独立地表示碳原子数为1-5的烷基或烷氧基。
本发明液晶组合物可以为为正性液晶组合物,所述液晶组合物还可以包含一种或多种式Ⅲ所示化合物
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;
m表示1或2;
Z3、Z4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。
式Ⅲ所示化合物优选为Ⅲ1-Ⅲ22化合物
其中,X1、X2各自独立的表示H或F,且不能同时为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的链烯基或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可以为负性液晶组合物,还可以包含一种或多种式Ⅳ所示的化合物
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中任一个CH2可以被环戊基、环丁基或环丙基替代;
Z5、Z6各自独立地表示单键、-CH2CH2-、-CH2O-;
m表示1或2;
n表示0、1或2。
式Ⅳ所示化合物优选为Ⅳ1-Ⅳ11化合物
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中任一个CH2可以被环戊基、环丁基或环丙基替代。
本发明液晶组合物可以为负性液晶组合物,还可以包含一种或多种式Ⅴ所示的化合物
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中任一个CH2可以被环戊基、环丁基或环丙基替代。
式Ⅴ所示的化合物优选为:
R81表示碳原子数为1-10的烷氧基。
液晶组合物各成分的不同比例,会表现出略有差异的性能,比如介电各向异性Δε、光学各向异性Δn、液晶的向列相转化为液体的转变温度点CP、低温下稳定性都会有所差异,可以应用于不同类型的显示器件,但是相同的特点是其旋转粘度γ1较低。应用于液晶显示器件,可以实现快速响应。
本发明所提供的液晶化合物中还可以加入手性剂。
手性剂优选(左旋或右旋):
本发明还涉及包含上述任意一种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无源矩阵显示元件或显示器。
所述液晶显示元件或液晶显示器优选有源矩阵寻址液晶显示元件或液晶显示器。
所述有源矩阵显示元件或显示器具体为TN-TFT或IPS-TFT液晶显示元件或显示器。
本发明所提供的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。
包含本发明所提供的液晶组合物的液晶材料,不但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。而且,作为薄膜晶体管技术(TFT-LCD)用液晶材料,还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。
附图说明
图1为式Ⅰ-a-1所示化合物的质谱图;
图2为式Ⅰ-b-1所示化合物的质谱图。
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。所述原料如无特别说明均能从公开商业途径而得。所述百分比如无特别说明,均为质量百分比。
下述实施例中,
CP表示清亮点,直接使用WRX-1S显微热分析仪测定,设定升温速率为3℃/min。
Δn表示光学各向异性(589nm,20℃),
Δε表示介电各向异性(25℃,1KHz,HP4284A,5.2微米TN左旋盒),
γ1表示20℃时旋转粘度(mpas),VHR(%)代表电荷保持率(5V,60Hz,20℃),ρ(×1013Ω·cm)代表电阻率(20℃)
电压保持率VHR(%)的测试仪与电阻率ρ(×1013Ω·cm)均为TOYO06254和TOYO6517型液晶物性评价***(测试温度20℃,时间16ms,测试盒为7.0微米)
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
表(二):端基与链接基团的对应代码
举例:
C(5)CCV1
3B B(3F)B(3F,5F)CF2O B(3F,5F)F
路线:
实施例1
路线:
操作流程:
2L三口瓶中加入4-环戊基环己基苯酚(95g,0.389mol),500ml石油醚,搅拌5min,加入39g浓硫酸,升温至70℃(水浴),滴加叔丁醇(151g,2.04mol)与100ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入300ml水,1LEA,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶3次,得57g,GC:99.88%,收率40%。
实施例2
路线:
2L三口瓶中加入4-(5’-环丁基四氢吡喃)苯酚(93g,0.4mol),500ml石油醚,搅拌5min,加入39g浓硫酸,升温至70℃(水浴),滴加叔丁醇(151g,2.04mol)与100ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入300ml水,1L乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶4次,得50g,GC:99.66%,收率35%。
实施例3
路线:
1L三口瓶中加入4-(5’-环丙基-1’,3’-二氧六环)苯酚(44g,0.2mol),300ml石油醚,搅拌5min,加入20g浓硫酸,升温至70℃(水浴),滴加叔丁醇(74g,1mol)与50ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入200ml水,500mL乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶4次,得33g,GC:99.5%,收率50%。
实施例4
路线
1L三口瓶中加入4’-环戊基-4-羟基-1,1’-联苯(47.6g,0.2mol),300ml石油醚,搅拌5min,加入20g浓硫酸,升温至70℃(水浴),滴加叔丁醇(74g,1mol)与50ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入200ml水,500mL乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶4次,得60g,GC:99.9%,收率85%。
实施例5
路线
2L三口瓶中加入4-环丙基苯酚(53.6g,0.4mol),500ml石油醚,搅拌5min,加入39g浓硫酸,升温至70℃(水浴),滴加叔丁醇(151g,2.04mol)与100ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入300ml水,1L乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶3次,得40g,GC:99.6%,收率40%。
实施例6
路线:
1L三口瓶中加入4-(环戊基氧基)苯酚(35.6g,0.2mol),300ml石油醚,搅拌5min,加入20g浓硫酸,升温至70℃(水浴),滴加叔丁醇(74g,1mol)与50ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入200ml水,500mL乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶4次,得29g,GC:99.75%,收率50%。
实施例7
1L三口瓶中加入4-(环戊基甲氧基)苯酚(38.4g,0.2mol),300ml石油醚,搅拌5min,加入20g浓硫酸,升温至70℃(水浴),滴加叔丁醇(74g,1mol)与50ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入200ml水,500mL乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶4次,得27.4g,GC:99.65%,收率45%。
实施例8
2L三口瓶中加入4-环丁基乙基苯酚(70.4g,0.4mol),500ml石油醚,搅拌5min,加入39g浓硫酸,升温至70℃(水浴),滴加叔丁醇(151g,2.04mol)与100ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入300ml水,1L乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶3次,得48.4g,GC:99.7%,收率42%。
实施例9
2L三口瓶中加入4-环丙基甲基苯酚(59.2g,0.4mol),500ml石油醚,搅拌5min,加入39g浓硫酸,升温至70℃(水浴),滴加叔丁醇(151g,2.04mol)与100ml石油醚混合液,滴加时间2h,控温70-72℃,滴完,保温4h;直接分液,分去硫酸,加入300ml水,1L乙酸乙酯,搅拌5min,分液,有机相直接旋干,1倍石油醚,3倍乙醇加热溶解产品,冰箱冷冻6小时,吸滤,重复结晶3次,得41.6g,GC:99.6%,收率40%。
以以下液晶组合物作为母体MUTY
液晶单体代码 | 含量(%) |
3CCV | 10 |
2CCB(3F)O1 | 6 |
2CCBO1 | 6 |
1BB5 | 8 |
3CBO2 | 6 |
3CCB(3F)2 | 6 |
3CCB2 | 5 |
2CCB(3F,4F) | 12 |
2CCBOCF3 | 8 |
C(5)BB(3F,5F)CF<sub>2</sub>OB(3F,4F,5F) | 17 |
C(5)C(3O)BB(3F,5F)CF<sub>2</sub>OB(3F,4F,5F) | 6 |
3CCBB(3F,4F) | 5 |
2CBB(2F)B3 | 5 |
分别添加不同结构的稳定剂500ppm,灌注液晶盒后,进行UV照射(5000mJ)实验,高热120℃保持三小时保存实验,测试其VHR数据,对比如下:
从上表可以看出,本发明所提供的稳定剂,相对于现有技术有更大的优势,对混合液晶能提供更好热抗性,从而为满足TFT显示对混合液晶越来越高的可靠性要求提供更好的保障。
本发明实施例所提供的式Ⅰ所代表的化合物作为添加剂应用于液晶组合物中,是在液晶组合物组分中额外添加,例如,添加1%的式Ⅰ-a-1,则表示为:
其他组分:100%
式Ⅰ-a-1:1%。
实施例10
实施例11
实施例12
实施例13
实施例14
实施例15
实施例16
实施例17
实施例18
由以上实施例可以看出:本发明的液晶组合物具有较低的旋转粘度γ1,用于液晶显示,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、高的对热的稳定性。尤其适合于TN、IPS、VA模式用液晶材料。
Claims (11)
5.根据权利要求4所述的液晶组合物,其特征在于,所述液晶组合物中式Ⅰ所示化合物总质量百分比含量为0.001-5%;式Ⅱ-1至Ⅱ-10所示化合物总质量百分比含量为1-60%;Ⅱ-11至Ⅱ-14所示化合物质量百分比含量为0-30%;
其中,R0、R2各自独立地表示碳原子数为1-5的烷基或碳原子数为2-5的烯基,R1,R3各自独立地表示碳原子数为1-5的烷基或烷氧基。
6.根据权利要求4所述的液晶组合物,其特征在于,所述液晶组合物为正性液晶组合物,还包含一种或多种式Ⅲ所示化合物
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;
m表示1或2;
Z3、Z4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。
7.根据权利要求6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Ⅲ1-Ⅲ22所示化合物中的一种或多种化合物
其中,X1、X2各自独立的表示H或F,且不能同时为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的链烯基或氟取代的碳原子数为3-8的链烯氧基。
11.一种包含权利要求4至10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,或者无源矩阵显示元件或显示器。
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3991139A (en) * | 1974-04-23 | 1976-11-09 | Showa Denko Kabushiki Kaisha | High heat stability composition of ring-opening polymerization product |
JPH06116556A (ja) * | 1992-10-09 | 1994-04-26 | Mitsui Toatsu Chem Inc | フェノール系シアニン色素の光安定化剤及び該光安定化剤を含有する光記録媒体 |
CN1408749A (zh) * | 2001-10-03 | 2003-04-09 | 伊斯曼柯达公司 | 显示器聚合物组件用稳定剂*** |
CN101620376A (zh) * | 2008-07-02 | 2010-01-06 | 富士胶片株式会社 | 压印用固化性组合物、使用了该组合物的固化物及其制造方法、以及液晶显示装置用部件 |
CN105295955A (zh) * | 2015-09-30 | 2016-02-03 | 石家庄诚志永华显示材料有限公司 | 一种正负混合液晶组合物 |
CN105589260A (zh) * | 2014-11-11 | 2016-05-18 | 三星显示有限公司 | 液晶显示装置 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19539141B4 (de) * | 1995-10-20 | 2016-07-07 | Merck Patent Gmbh | 2,6-Di-tert.-butylphenole |
DE102009022309A1 (de) * | 2009-05-22 | 2010-11-25 | Merck Patent Gmbh | Flüssigkristallanzeige |
DE102011108708A1 (de) * | 2010-09-25 | 2012-03-29 | Merck Patent Gmbh | Flüssigkristallanzeigen und flüssigkristalline Medien mit homöotroper Ausrichtung |
JP5784746B2 (ja) * | 2010-12-10 | 2015-09-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | 液晶媒体および電気光学的ディスプレイ |
CN103030534B (zh) * | 2012-11-23 | 2015-02-04 | 石家庄诚志永华显示材料有限公司 | 含有2,3-二氟苯基的负性液晶化合物及其制备方法与应用 |
CN103254356B (zh) * | 2013-04-25 | 2016-01-13 | 深圳市华星光电技术有限公司 | 可聚合混合物及其液晶组合物 |
CN104650923B (zh) * | 2015-02-15 | 2017-10-20 | 石家庄诚志永华显示材料有限公司 | 液晶组合物及其应用 |
-
2016
- 2016-06-06 CN CN201610392022.6A patent/CN107459993B/zh active Active
- 2016-08-02 TW TW105124448A patent/TWI616432B/zh active
-
2017
- 2017-05-03 US US15/585,312 patent/US10858591B2/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3991139A (en) * | 1974-04-23 | 1976-11-09 | Showa Denko Kabushiki Kaisha | High heat stability composition of ring-opening polymerization product |
JPH06116556A (ja) * | 1992-10-09 | 1994-04-26 | Mitsui Toatsu Chem Inc | フェノール系シアニン色素の光安定化剤及び該光安定化剤を含有する光記録媒体 |
CN1408749A (zh) * | 2001-10-03 | 2003-04-09 | 伊斯曼柯达公司 | 显示器聚合物组件用稳定剂*** |
CN101620376A (zh) * | 2008-07-02 | 2010-01-06 | 富士胶片株式会社 | 压印用固化性组合物、使用了该组合物的固化物及其制造方法、以及液晶显示装置用部件 |
CN105589260A (zh) * | 2014-11-11 | 2016-05-18 | 三星显示有限公司 | 液晶显示装置 |
CN105295955A (zh) * | 2015-09-30 | 2016-02-03 | 石家庄诚志永华显示材料有限公司 | 一种正负混合液晶组合物 |
Non-Patent Citations (3)
Title |
---|
Barbara T.Walton et al..Structure-activity relationships for insect growth regulators derived from substituted di-tert-butyl phenols.《Pesticide Biochemistry and Physiology》.2004,第12卷(第1期),23-30. * |
Jaehwi Lee et al..Mechanism of Oxygenation of 2,6-Di-tert-butylphenol Derivative.《Bull. Korean Chem. Soc.》.2006,第27卷(第1期),33-34. * |
James R. Frost et al..Iridium-Catalyzed C4-Alkylation of 2,6-Di-tert-butylphenol by Using Hydrogen-Borrowing Catalysis.《Synthesis》.2016,第49卷910-916. * |
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