CN108264498B - 化合物、包含该化合物的液晶介质及其应用 - Google Patents
化合物、包含该化合物的液晶介质及其应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及液晶化合物领域。更具体地,涉及一种化合物、包含该化合物的液晶介质及其应用。
背景技术
自1888年奥地利科学家莱尼茨尔第一次合成出来了液晶以来,液晶产业真正的发展是近30多年的事,由于液晶显示材料具有明显的优点,如驱动电压低、功耗微小、可靠性高、显示信息量大、彩色显示、无闪烁、可以实现平板显示等,液晶单体和液晶显示都经历了巨大的的发展,液晶单体目前已合成了1万多种液晶材料,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、二氟甲氧桥类、乙烷类及杂环类等。液晶显示也从30年前的黑白小屏幕的TN、STN发展到现在彩色大屏幕的TN-TFT、VA-TFT、IPS-TFT、PDLC等。
新型液晶显示方式主要有光学补偿弯曲模式(OCB)、共面转变液晶显示(IPS)、垂直取向模式(VA)、轴对称微结构液晶显示(ASM)、多畴扭曲液晶显示等。
各种显示方式液晶盒的设计不同、驱动方式不同,液晶分子指向矢和玻璃基板方向不同,光学补偿弯曲模式(OCB)、共面转变液晶显示(IPS)液晶分子指向矢和玻璃基板方向是平行的,而垂直取向模式(VA)、轴对称微结构液晶显示(ASM)在无电场状态下液晶分子指向矢和玻璃基板方向垂直。
平行排列方式的IPS,液晶的介电各向异性(△ε)既可以是正的,也可以是负的。
垂直取向模式(VA)所有液晶分子在零场时和玻璃基板方向垂直,与垂直入射光线平行。当偏振片正交时,会显示良好的暗态,所以该类器件有良好的对比度,用到液晶的介电各向异性(△ε)必须是负的。液晶的光学各向异性(△n)、液晶盒的厚度(d)、入射光的波长(λ)几乎影响不到对比度。垂直取向模式(VA)的响应时间比扭曲型器件要短得多,约为一半左右。在外加电压影响下,VA器件主要产生的是液晶分子的弯曲形变,ECB产生的是液晶分子的展曲形变,而扭曲显示产生的是液晶分子的扭曲形变,其响应时间也分别与弯曲、展曲、扭曲弹性常数成反比,由于大部分的液晶在通常的情况下液晶的弯曲弹性常数大于展曲弹性常数,展曲弹性常数又大于扭曲弹性常数,这也是VA器件响应时间较快的原因。
对于现有的一些结构类似其中,R1和R2分别独立的选自链烷基、链烷氧基等的化合物,由于侧向二氟及分子内存在刚性结构硫芴限制二苯环之间的偏转,使得这类化合物具有较高的介电各向异性的绝对值,以及很高的双折射。但也因为刚性硫芴环的存在,此类烷基取代的液晶化合物互溶性较差,低温下易析出。
因此,为了能使显示器件的性能更加接近理想化,需要提供新的液晶化合物,使其能更好的应用于显示器件。
发明内容
为解决以上技术问题,本发明的第一个目的在于提供一种化合物。
本发明的第二个目的在于提供一种液晶介质。
本发明的第三个目的在于提供液晶介质在制备液晶混合物、液晶显示器件材料或电光学显示器件材料中的应用。
为达到上述第一个目的,本发明采用下述技术方案:
一种化合物,所述化合物的结构式如下式I所示:
其中:
R表示环丙基、环戊基和2-四氢呋喃基中的一种;
Z表示单键、-CH2-、-O-、-CH2CH2-、-CH2O-、-CF2O-和-COO-中的一种;
X表示H、F、碳原子数为1-7的烷基和碳原子数为1-7的烷氧基中的一种,其中,碳原子数为1-7的烷基和碳原子数为1-7的烷氧基中,一个或多个H原子能被F代替。
优选地,所述结构式为式I的化合物的结构式具体如下式I1至式I17所示:
其中:
R表示环丙基、环戊基和2-四氢呋喃基中的一种;
R1表示碳原子数为1-7的烷基或碳原子数为1-7的烷氧基,其中,一个或多个H原子能被F代替。
优选地,所述结构式为式I的化合物的结构式具体如下式I1-1至式I17-1所示:
优选地,本发明中,上述结构式为式I的化合物可包括但不限于采用如下合成路径合成:
根据上述合成路径,式II和式III是合成目标化合物也即式I的化合物的关键中间体。
合成式I所示化合物的关键中间体式II和式III可通过商业途径购买而得,也可参考Org.Biomol.Chem.,2003,1,1609-1624和EP2399896中的相似化合物的合成方法制备获得。此类方法原理、操作过程、常规后处理、过硅胶柱、重结晶提纯等手段是本领域合成人员所熟知的,完全可以实现合成过程,得到目标产物。
上述所有方法的所有步骤的反应均在溶剂中进行;所述溶剂均选自四氢呋喃、N,N-二甲基甲酰胺、乙醇、甲醇、二氯甲烷、丙酮、甲苯和去离子水中的至少一种。
为达到上述第二个目的,本发明提供一种液晶介质,该液晶介质包含一种或多种上述结构式为式I的化合物。
优选地,所述液晶介质还包含一种或多种结构式为式IV的化合物,作为第二组分:
其中:
R2、R3各自独立地表示下列①-③所示基团中的任一基团:
①.碳原子数为1-7的直链烷基或碳原子数为1-7的直链烷氧基;
②.所述①所示任一基团中的一个或多个-CH2-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基团;
③.所述①所示任一基团中的一个或多个H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基团;
m、n、o各自独立地表示0或1;
优选地,所述液晶介质还包含一种或多种结构式为式V的化合物:
其中:
R4、R5各自独立地表示碳原子数为1-10的烷基或碳原子数为2-10的链烯基;其中,任意的-CH2-能被-CH2O-、-OCH2-、-C=C-代替,任意的H原子能被F代替;
p、q、r各自独立地表示0或1;
优选地,所述液晶介质中,结构式为式I的化合物的质量百分含量为1-24%、结构式为式IV的化合物的质量百分含量为35-58%、结构式为式V的化合物的质量百分含量为30-46%。
优选地,所述结构式为式IV的化合物的结构式具体如下式IV1至式IV15所示:
其中:
R2、R3各自独立地表示下列①-③所示基团中的任一基团:
①.碳原子数为1-7的直链烷基或碳原子数为1-7的直链烷氧基;
②.所述①所示任一基团中的一个或多个-CH2-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基团;
③.所述①所示任一基团中的一个或多个H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基团;
优选地,所述结构式为式V的化合物的结构式具体如下式IV1至式IV16所示:
其中:
R4,R5各自独立地表示碳原子数为1-10的烷基或碳原子数为2-10的链烯基;其中,任意的-CH2-能被-CH2O-、-OCH2-或-C=C-代替,任意的H原子能被F代替;(F)各自独立地表示F或H。
上述液晶介质在制备液晶混合物、液晶显示器件材料或电光学显示器件材料中的应用也在本发明的保护范围中。
本发明的有益效果如下:
由于分子内刚性结构和侧向二氟的存在,硫芴类液晶表现出较大的负性介电常数,但刚性结构的存在也使此类化合物溶解性较差,限制其应用。令人惊奇的是,当在硫芴类液晶分子内引入环丙基、环戊基和2-四氢呋喃基中的一种作为链端基时,所得液晶化合物与传统含柔性烷基链的此类液晶化合物表现出更好的互溶性,故利用本发明提供的式I所示化合物可改善液晶化合物的互溶性,改善混晶低温稳定性,拓展液晶混合物的应用范围,具有重要的应用价值。
附图说明
下面结合附图对本发明的具体实施方式作进一步详细的说明。
图1示出实施例4式I12-2的化合物的质谱图。
具体实施方式
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
本发明中,制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得,所述百分比如无特殊说明,均为质量百分比。
本发明中,各符号的具体意义及测试条件如下:
GC表示气相色谱纯度,MP表示熔点,CP表示清亮点,MS表示质谱,Δε表示介电各向异性,Δn表示光学各向异性。
测定GC、MP、CP、MS、Δε和Δn的方法均为常规方法。
实施例1
结构式为式I1-1的化合物:
其制备路线如下:
步骤1:
1L三口瓶中加入36.3g(0.14mol)2-氟-6-溴-3-环戊基苯酚,22.6g(0.14mol)2,3-二氟苯硼酸,43g(0.31mol)碳酸钾,300ml甲苯和100ml纯水搅拌至全溶,氮气保护下加入0.05g Pd-132,加热回流反应6h;停止反应,加400ml纯水搅拌分液,水层用200ml×2甲苯萃取,合并有机层,用400ml×2饱和食盐水洗涤,减压旋干溶剂,所得液体加80g石油醚搅拌均匀,-20℃重结晶,得白色固体(1-a)33g,GC:98.5%,收率80.6%。
步骤2:
1L三口瓶中加入33g(0.11mol)(1-a),21.5g(0.17mol)二甲氨基硫代甲酰氯,22.2g(0.22mol)三乙胺和300ml二氯甲烷室温搅拌反应6h;停止反应,加400ml纯水搅拌分液,水层用200ml×2二氯甲烷萃取,合并有机层,用400ml×2饱和碳酸氢钠水洗涤,无水硫酸钠干燥后减压旋干溶剂,所得液体加100g石油醚搅拌均匀,-20℃重结晶,得白色固体(1-b)35g,GC:98.0%,收率83%。
步骤3:
1L三口瓶中加入35g(0.092mol)(1-b),300ml甲苯搅拌至全溶,氮气保护下加入0.94g Pd(PtBu3)2,加热至100℃反应4h;停止反应,加400ml纯水搅拌分液,水层用200ml×2甲苯萃取,合并有机层,用400ml×2饱和食盐水洗涤,减压旋干溶剂,所得液体加100g石油醚搅拌均匀,-20℃重结晶,得白色固体(1-c)30g,GC:99.1%,收率86%。
步骤4:
在500ml三口瓶中加入30g(0.08mol)(1-c),氮气保护下加入200ml二甲基亚砜(DMSO),搅拌均匀,加入8.8g(0.22mol)60%氢化钠矿物油,加热至100℃搅拌4小时;停止反应,冷却至室温,将反应液倒入300g冰水中搅拌,析出大量固体,滤布吸滤得固体,晾干,加200ml石油醚加热全溶后过30g热硅胶柱,用200ml热石油醚冲柱,旋干溶液,1倍甲苯和1倍石油醚加热全溶,0℃重结晶两次,得白色固体(I1-1)15g,GC:99.92%,收率65%。
实施例2
结构式为式I6-2的化合物:
其制备路线如下:
步骤1:
以2-氟-6-溴-3-环戊基苯酚和2,3-二氟-4-三氟甲氧基苯硼酸为原料,参考实施例1中步骤1,合成下述式2-a的化合物:
步骤2:
以化合物2-a为原料,参考实施例1中步骤2合成的方法合成式2-b化合物:
步骤3:
以化合物2-b为原料,参考实施例1中步骤3合成式2-c化合物:
步骤4:
以化合物2-c为原料,参考实施例1中步骤4合成目标化合物结构式为式I6-2的化合物:
实施例3
结构式为式I12-1的化合物:
其制备路线如下:
步骤1:
以2-氟-6-溴-3-环丙甲氧基苯酚和2,3-二氟-4-乙氧基苯硼酸为原料,参考实施例1中步骤1,合成下述式3-a的化合物:
步骤2:
以化合物3-a为原料,参考实施例1中步骤2合成的方法合成式3-b化合物:
步骤3:
以化合物3-b为原料,参考实施例1中步骤3合成3-c化合物:
步骤4:
以化合物3-c为原料,参考实施例1中步骤4合成目标化合物结构式为式I12-1的化合物:
实施例4
结构式为式I12-2的化合物:
其制备路线如下:
步骤1:
以2-氟-6-溴-3-环戊甲氧基苯酚和2,3-二氟-4-丁氧基苯硼酸为原料,参考实施例1中步骤1,合成下述式4-a的化合物:
步骤2:
以化合物4-a为原料,参考实施例1中步骤2合成的方法合成式4-b化合物:
步骤3:
以化合物4-b为原料,参考实施例1中步骤3合成4-c化合物:
步骤4:
以化合物4-c为原料,参考实施例1中步骤4合成目标化合物结构式为式I12-2的化合物:
得到的式I12-2的化合物的质谱图如图1所示。
实施例5
结构式为式I15-2的化合物:
其制备路线如下:
步骤1:
以2-氟-6-溴-3-(2-四氢呋喃)乙基苯酚和2,3-二氟-4-丁氧基苯硼酸为原料,参考实施例1中步骤1,合成下述式5-a的化合物:
步骤2:
以化合物5-a为原料,参考实施例1中步骤2合成的方法合成式5-b化合物:
步骤3:
以化合物5-b为原料,参考实施例1中步骤3合成5-c化合物:
步骤4:
以化合物5-c为原料,参考实施例1中步骤4合成目标化合物结构式为式I15-2的化合物:
混合物实施例
实施例6-13:
实施例6-13列出了不同液晶介质的制备方法,其中,各实施例具体化合物的单体结构、用量(重量百分含量)、所得的液晶介质的性能参数测试结果分别如下表1-8所示。
各实施例中所涉及的温度单位为℃,其他符号的具体意义及测试条件如下:
S-N表示液晶的晶态到向列相的熔点(℃);
c.p.表示液晶的清亮点(℃),测试仪器:Mettler-Toledo-FP System显微热分析仪;
γ1为旋转粘度(mPa·s),测试条件为:25℃、INSTEC:ALCT-IR1、18微米垂直盒;
K11为扭曲弹性常数,K33为展曲弹性常数,测试条件为:25℃、INSTEC:ALCT-IR1、18微米垂直盒;
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:25℃、INSTEC:ALCT-IR1、18微米垂直盒;
Δn表示光学各向异性,Δn=no-ne,其中,no为寻常光的折射率,ne为非寻常光的折射率,测试条件:589nm、25±0.2℃。
本发明中,分别按比例称取通式I、IV和V的化合物,制备得到液晶介质,其中液晶介质的制备所用的设备和仪器为:
(1)电子精密天平(精确度0.1mg);
(2)不锈钢烧杯:用于称量化合物原料;
(3)勺子:用于加入原料;
(4)磁力转子:用于搅拌;
(5)控温电磁搅拌器。
液晶介质的制备方法包括以下步骤:
(1)将所用原料按顺序摆放整齐;
(2)把不锈钢烧杯放置在天平上,用小勺将式I的化合物盛入不锈钢烧杯中;
(3)依次按所需重量添加其他化合物原料;
(4)把加好料的不锈钢烧杯放置在磁力搅拌仪器上加热融化;
(5)待不锈钢烧杯中混合物大部份融化后,往不锈钢烧杯中加入一颗磁力转子,将液晶混合物搅拌均匀,冷却到室温后即得液晶介质。
将所得的液晶介质填充于液晶显示器两基板间进行性能测试。
表1实施例6的液晶介质的组分配比及其性能参数
表2实施例7的液晶介质的组分配比及其性能参数
表3实施例8的液晶介质的组分配比及其性能参数
表4实施例9的液晶介质的组分配比及其性能参数
表5实施例10的液晶介质的组分配比及其性能参数
表6实施例11的液晶介质的组分配比及其性能参数
表7实施例12的液晶介质的组分配比及其性能参数
表8实施例13的液晶介质的组分配比及其性能参数
对比例1
配方如下表9所示,其组分中不包含结构式为式I的化合物,而包含结构式为式VI的化合物。
对比例2
配方如下表10所示,其组分中不包含结构式为式I的化合物,而包含结构式为式VII的化合物。
表9对比例1的液晶介质的组分配比及其性能参数
表10对比例2的液晶介质的组分配比及其性能参数
由实施例6-13所示的液晶组合物的性能参数可知,本发明的液晶组合物具有很好的互溶性和极大的负性介电常数,而实施例10和对比例1、对比例2对比可知,以环丙基、环戊基和2-四氢呋喃基为端基的硫芴类液晶化合物与传统以柔软的烷基链为端基的硫芴类液晶相比时表现出很好的互溶性,低温稳定性也相应提高,故利用本发明提供的式I所示化合物可改善液晶化合物的互溶性,拓展液晶混合物的应用范围,具有重要的应用价值。
本发明虽然仅仅列举了上述8个实施例及对比例的具体化合物及其配比用量(重量百分含量),并进行了性能测试,但是本发明的液晶组合物可以在上述实施例的基础上,利用本发明所涉及的式I、IV、V所代表的液晶化合物、以及式I、IV、V的优选液晶化合物进行进一步拓展和修改,通过对其配比用量进行适当调整,均能达到本发明的目的。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动,这里无法对所有的实施方式予以穷举,凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (6)
1.一种液晶介质,其特征在于,包含一种或多种结构式如下式I所示的化合物:
其中:
R表示环丙基、环戊基和2-四氢呋喃基中的一种;
Z表示单键、-O-、-CH2CH2-、-CH2O-、-CF2O-和-COO-中的一种;
X表示H、F、碳原子数为1-7的烷基和碳原子数为1-7的烷氧基中的一种,其中,碳原子数为1-7的烷基和碳原子数为1-7的烷氧基中,一个或多个H原子能被F代替;
所述液晶介质还包含一种或多种结构式为式IV的化合物:
其中:
R2、R3各自独立地表示下列①-③所示基团中的任一基团:
①.碳原子数为1-7的直链烷基或碳原子数为1-7的直链烷氧基;
②.所述①所示任一基团中的一个或多个-CH2-被-O-、-COO-、-OOC-或-CH=CH-代替所形成的基团;
③.所述①所示任一基团中的一个或多个H原子被F、Cl、-CH=CH2或-CH=CH-CH3代替所形成的基团;
m、n、o各自独立地表示0或1;
3.根据权利要求2所述的液晶介质,其特征在于,所述液晶介质中,结构式为式I的化合物的质量百分含量为1-24%、结构式为式IV的化合物的质量百分含量为35-58%、结构式为式V的化合物的质量百分含量为30-46%。
6.如权利要求1-5任一项所述的液晶介质在制备液晶混合物、液晶显示器件材料或电光学显示器件材料中的应用。
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