WO2013067768A1 - 用于2d/3d显示切换开关的液晶介质 - Google Patents

用于2d/3d显示切换开关的液晶介质 Download PDF

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WO2013067768A1
WO2013067768A1 PCT/CN2012/001506 CN2012001506W WO2013067768A1 WO 2013067768 A1 WO2013067768 A1 WO 2013067768A1 CN 2012001506 W CN2012001506 W CN 2012001506W WO 2013067768 A1 WO2013067768 A1 WO 2013067768A1
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liquid crystal
crystal medium
compound
group
weight
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French (fr)
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韩文明
吴凤
宋晓龙
张宏伟
谭玉东
陈亮
王毅明
马定福
陈法兵
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江苏和成显示科技股份有限公司
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    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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    • C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
    • C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
    • C09K2019/181—Ph-C≡C-Ph
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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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    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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    • C09K19/3001—Cyclohexane rings
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Definitions

  • the present invention relates to a liquid crystal medium, particularly a liquid crystal medium for a 2D/3D display changeover switch, and a 2D/3D display changeover switch including the liquid crystal medium.
  • BACKGROUND OF THE INVENTION The manner of realizing 3D display can be divided into wearing glasses and naked eyes. The specific implementation and principle can be obtained from Kong Lingsheng, etc., China Optics and Applied Optics, Vol. 2, No. 2, pp. 112-118; Xu Jingyi and Huang Yibai , Optical Engineering, Ninety-eighth Month; Nicolas S. Holliman, Neil A. Dodgson, Gregg E.
  • One aspect of the present invention provides a liquid crystal medium for a 2D/3D display changeover switch, comprising:
  • R, R 2 and R 3 each independently represent a fluorenyl group having 1-8 carbon atoms which is unsubstituted or at least monosubstituted by halogen, and, optionally, one or more of the alkyl groups are not phased
  • X represents F, Cl, CN, SCF 5 , NCS, or a halogenated fluorenyl group, a halogenated alkenyl group, a halogenated alkoxy group or a halogenated alkenyloxy group each having up to 4 carbon atoms; preferably, X represents OCF 3 , F, CI or CN;
  • R, R 2 are as defined in claim 1.
  • the compound of formula II is selected from at least one compound comprising formula II-1 to ⁇ -23:
  • the individual compounds of formula I, formula II, and other compounds useful in the present invention are known or can be prepared by methods analogous to known compounds.
  • the liquid crystal medium used in accordance with the present invention is prepared in a manner conventionally used in its own right. Generally, the desired amount of the component is dissolved in a minor amount in the component constituting the main component, desirably at an elevated temperature. It is also possible to dissolve the components in an organic solvent, for example, a solution in acetone, chloroform or toluene, and after thorough mixing, remove the solvent by distillation.
  • the dielectric may also include other additives known to those skilled in the art and described in the literature, such as stabilizers and antioxidants.
  • the liquid crystal medium has an advantageous value of ⁇ , and a relatively high and relatively low V 9 o V is sufficient to achieve switching between 2D/3D displays, and has a good 2D or 3D display effect.
  • nCCPm The structure is expressed as the code listed in Table 1, and can be expressed as: nCCPm, where n in the code indicates the left-end ⁇
  • the number of C atoms for example, n is "3", meaning that the alkyl group is -C 3 H 7 ; C in the code represents a cyclohexyl group; P in the code represents a phenylene group; m in the code represents a right-end fluorenyl group
  • the number of C atoms, for example, m is "1", which means that the thiol group at the right end is -CH 3 .
  • the individual compounds and other compounds used in the following examples are known or can be prepared by methods analogous to known compounds.
  • the liquid crystal mixture used in accordance with the present invention is prepared in a manner conventionally used in its own right.
  • the desired amount of the component is dissolved in a minor amount in the component constituting the main component, desirably at an elevated temperature.
  • Table 2 shows the chiral dopants commonly used in the mixtures of the invention.
  • Example 2 According to the method of Example 1, the liquid crystal medium of the invention was prepared according to the respective compounds and weight percentages listed in Table 4, and the performance test was carried out. The test data are also shown in Table 4. Table 4
  • Example 3 According to the method of Example 1, the liquid crystal medium of the present invention was prepared according to the respective compounds and weight percentages listed in Table 5, and the performance test was carried out. The test data are also shown in Table 5. table 5
  • Example 4 According to the method of Example 1, the liquid crystal medium of the invention was prepared according to the respective compounds and weight percentages listed in Table 6, and the performance test was carried out. The test data are also shown in Table 6. Table 6
  • Example 6 According to the method of Example 1, the liquid crystal medium of the present invention was formulated according to the respective compounds and weight percentages listed in Table 8, and the performance test was carried out. The test data are also shown in Table 8. Table 8
  • Example 7 According to the method of Example 1, the liquid crystal medium of the invention was prepared according to the respective compounds and weight fractions listed in Table 9, and the performance test was carried out. The test data are also shown in Table 9. Table 9
  • Example 8 According to the method of Example 1, the liquid crystal medium of the present invention was prepared according to the respective compounds and weight percentages listed in Table 10, and the performance test was carried out. The test data are also shown in Table 10. Table 10
  • Example 9 According to the method of Example 1, the liquid crystal medium of the present invention was formulated according to the respective compounds and weight percentages listed in Table 11, and the performance test was carried out. The test data are also shown in Table 11. Table 1 1
  • Example 10 According to the method of Example 1, the liquid crystal medium of the present invention was prepared according to the respective compounds and weight percentages listed in Table 12, and the performance test was carried out. The test data are also shown in Table 12. Table 12

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  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
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Abstract

一种用于2D/3D显示切换开关的液晶介质，该液晶介质包括一种液晶组合物，所述液晶组合物包含基于所述液晶介质总重量20-99%的至少一种结构式I的化合物和基于所述液晶组合物总重量1-80%的至少一种结构式II的化合物。该液晶介质具有有利的△n数值，相对较高的TN-I和相对较低的V90/V10，非常适用于控制2D/3D显示间切换的液晶开关。本发明还提供包含所述液晶介质的2D/3D显示切换开关。

Description

用于 2D/3D显示切换开关的液晶介质 技术领域 本发明涉及液晶介质，尤其是用于 2D/3D显示切换开关的液晶介质以及包含该液晶介 质的 2D/3D显示切换开关。 背景技术 实现 3D显示的方式可以分为戴眼镜式和裸眼式，具体实现方式及原理可从孔令胜等， 中国光学与应用光学， 第 2卷， 第 2期， 112-118页； 许精益和黄乙白， 光学工程， 第九 十八其月； Nicolas S. Holliman, Neil A. Dodgson, Gregg E. Favalora 禾口 Lachlan pocket, Ieeetransactions on broadcasting, Vol. 57, No. 2, page 362-371中获知。裸眼 3D显示的一个缺 点是其在显示 2D画面时（例如， 文字）， 由于分辨率不足， 导致显示质量下降。 解决这一 问题较好的办法就是在柱透镜式 3D显示方式的基础上， 加上一个可控的 2D/3D显示之间 切换的液晶开关。这些可从 Uehara, shin-ichi等， EP1394593B1 ; "Switchable lenticular based 2D/3D displays (基于 2D/3D显示的可切换透镜） " Dick K.Gde Boer等， SPIE-IS&T, Vol. 6490， 49000R; "Overview of 3D/2D switchable liquid crystal display technologies (2D/3D可 切换液晶显示技术） " Byoungho Lee和 Jae-Hyeung Park, Proc. Of SPIE Vol.7618,761806; "Switchable 2D/3D display-Solid Phase Liquid Crystal Microlens Array (可切换的 2D/3D显示 -固相液品微透镜阵列）" J. Harrold, D. j. Wilkes和 G. J. Woodgate中获知。然而，用于 2D/3D 显示之间切换的液品开关中的液晶介质却尚未发现有提及。 因此， 对于能够用于 2D/3D显示切换开关的液品介质， 存在巨大的需求。 发明内容 本发明的目的是提供用于 2D/3D显示切换开关的液晶介质。 现已发现， 若使用包括一种或多种通式 I的化合物和至少一种通式 Π的化合物， 则可 实现该目的。 本发明的一个方面提供一种用于 2D/3D显示切换开关的液晶介质， 包括：
基于所述液晶组合物总重量 20-99%的至少一种结构式 I的化合物和基于所述液品组 合物总重量 1-80%的至少一种结构式 II的化合物，
Figure imgf000004_0001
Figure imgf000004_0002
其中
R,、 R2和 R3分别独立地表示未取代或被卤素至少单取代的具有 1-8个碳原子的垸基， 并且， 可选地， 所述烷基中的一个或多个不相邻的 -CH2-基团可被 -0-、 -S -、 -CH=CH -、 -CF=CF -、 -COO-, -OCO-、 -OOC -、 -C≡C -、 3-5个碳原子的环烷烃所替代； 优选地， R,、 R2和 分别独立地表示具有 1-8个碳原子的烷基、 垸氧基或链烯基；
X表示 F、 Cl、 CN、 SCF5、 NCS、 或者各自具有至多 4个碳原子的卤代垸基、 卤代 链烯基、 卤代烷氧基或卤代链烯氧基； 优选地， X表示 OCF3、 F、 CI或 CN;
Z,、 Z2、 Z3、 Z4和 Z5 分别独立地表示单键、 -CH2CH2-、 -CF2CF2-、 -CF2CH2-、 -CH2CF2-、 -CH=CH -、 -CF=CF -、 -CF=CH -、 -CH=CF- -C≡C -、 -COO-、 -OCO-、 -CH20-、 -OCH2-、 -CF20-或 -OCF2-; 优选地， Z卜 Z2、 Z3、 Z4 IP Z5 分别独立地表示单键、 -C≡C -或 -COO-; a、 b和 c 分别独立地表示 0、 1或 2， 其中， a+b≤2;
Figure imgf000004_0003
分别独立 地表示未取代或被 1-4个氟原子取代的 1,4-亚环己基、 1,4-亚环己烯基或 1,4-亚环己二烯基， 并且， 可选地， 所述未取代或被取代的 1,4-亚环己基、 1,4-亚环己烯基或 1,4-亚环己二烯 基中的一个或两个彼此不相邻的 -CH2-基团可分别独立地被 -0-或 -S-替代； 或者
Figure imgf000004_0004
—分别独立 地表示 1,4-亚苯基， 并且， 可选地， 所述 1,4-亚苯基被一个或两个氟原子或氯原子取代， 可选地， 所述 1，4-亚苯基中一个或两个 -CH-基团被 N取代； 或者
Figure imgf000004_0005
-分别独立 地表示 1,4-亚双环 [2.2.2]辛基、 萘 -2,6-二基、 反式-十氢化萘 -2,6-二基、 四氢化萘 -2，6-二基、 茚 -2,5-二基， 其中的一个或多个氢原子可以独立地被一个或多个卤原子取代；
Figure imgf000005_0001
Figure imgf000006_0001
90ST00/Z10ZN3/X3d
Figure imgf000007_0001
其中， R,、 R2如权利要求 1中所定义。
优选地， 所述结构式 II的化合物选自包括通式 II-1到 Π-23的至少一种化合物:
Figure imgf000007_0002
Figure imgf000008_0001
Figure imgf000009_0001
以及
Figure imgf000009_0002
其中， 如权利要求 1中所定义， L!、 L2彼此独立地表示 11或？。 在优选的实施方案中，本发明的所述液晶介质包含 40wt%-95wt%结构式 I的化合物以 及 5wt%-60wt%结构式 II的化合物。 更优选地， 包含 50wt%-85wt%结构式 I的化合物以及 15wt%-50wt%结构式 II的化合物。 本发明的再一个方面提供一种包含如上所述的液晶介质的 2D/3D显示切换开关。 本发明的另一个方面提供所述的液晶介质在制备用于 2D/3D显示切换开关中的应用。 用于本发明的式 I、 式 II的各化合物， 以及其他化合物是巳知的或可通过类似于已知 化合物的方法制备。 根据本发明所使用的液晶介质是按照本身常用的方式来制备的。 一般， 将所需量的组 分以较少量溶于构成主要成分的组分中， 理想地在升高温度下。 还有可能将各组分溶在有 机溶剂中， 例如在丙酮、 氯仿或甲苯中的溶液进行混合， 在彻底混合之后， 再通过蒸馏除 去溶剂。 电介质也可包括本领域中技术人员已知的和在文献中描述的其他添加剂，如稳定剂和 抗氧化剂。 例如能够添加 0-15%的手性惨杂剂。 根据本发明液晶介质具有有利的 Δη数值， 相对较高的 和相对较低的 V9o V 够实现 2D/3D显示之间的切换， 并且有好的 2D或 3D的显示效果。
具体实施方式
需要说明的是， 各实施例用于说明本发明， 而不代表一种限制。
为便于表达， 以下各实施例中， 液晶化合物的基团结构用表 1所列的代码表示：
Figure imgf000010_0002
以如下结构式的化合物为例:
Figure imgf000010_0001
该结构式如用表 1所列代码表示， 则可表达为： nCCPm, 代码中的 n表示左端垸基的 C原子数， 例如 n为 " 3 "， 即表示该烷基为 -C3H7 ; 代码中的 C代表环己垸基； 代码中的 P 代表亚苯基； 代码中的 m表示右端垸基的 C原子数， 例如 m为 " 1 "， 即表示右端的垸基 为 -CH3 。 用于以下实施例中的各化合物以及其他化合物是已知的或可通过类似于已知化合物 的方法制备。 根据本发明所使用的液晶混合物是按照本身常用的方式来制备的。 一般， 将所需量的 组分以较少量溶于构成主要成分的组分中， 理想地在升高温度下。 还有可能将各组分溶在 有机溶剂中， 例如在丙酮、 氯仿或甲苯中的溶液进行混合， 在彻底混合之后， 再通过蒸馏 除去溶剂。 表 2示出了常在本发明混合物中使用的手性掺杂剂。
Figure imgf000012_0001
以下实施例中各测试项目的简写代号分别表示为:
清亮点 （向列-各向同性相转变温度）
Vise. 流动粘度 （mm2 * s— 20 , 除非另有说明）
no 普通折射率 （589nm， 20°C )
Δη 光学各向异性 （589nm， 20°C )
Δ ε 介电各向异性 （ΙΚΗζ, 25 °C )
V,o 阈值电压 (V)
ν90 饱和电压 (V) 流动粘度 Vise使用锥板粘度计进行测试；折射率及折射率各向异性使用阿贝折光仪在 钠光灯 （589nm) 光源下、 20°C测试得。 实施例 1 依据表 3所列的各化合物及重量百分数， 按照本领域的常规方法（如采取加热、 超声 波、 悬浮等方式） 配制成本发明的液晶介质。 对所得到的液晶介质其进行性能测试， 测试数据也列于表 3。 表 3
Figure imgf000013_0001
实施例 2 依据实施例 1的方法，按表 4所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 4。 表 4
Figure imgf000014_0001
实施例 3 依据实施例 1的方法，按表 5所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 5。 表 5
Figure imgf000015_0001
实施例 4 依据实施例 1的方法，按表 6所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 6。 表 6
Figure imgf000016_0001
实施例 依据实施例 1的方法，按表 7所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 7。 表 7
Figure imgf000017_0001
实施例 6 依据实施例 1的方法，按表 8所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 8。 表 8
Figure imgf000018_0001
实施例 7 依据实施例 1的方法， 按表 9所列的各化合物及重量分数配制成本发明的液晶介质, 其进行性能测试， 测试数据也列于表 9。 表 9
Figure imgf000019_0001
实施例 8 依据实施例 1 的方法， 按表 10所列的各化合物及重量百分数配制成本发明的液晶介 质， 其进行性能测试， 测试数据也列于表 10。 表 10
Figure imgf000020_0001
实施例 9 依据实施例 1的方法，按表 11所列的各化合物及重量百分数配制成本发明的液晶介质， 其进行性能测试， 测试数据也列于表 11。 表 1 1
Figure imgf000021_0001
实施例 10 依据实施例 1 的方法， 按表 12所列的各化合物及重量百分数配制成本发明的液晶介 质， 其进行性能测试， 测试数据也列于表 12。 表 12
Figure imgf000022_0001
在上述液晶介质中加入按总重量计 0.1%的手性掾杂剂 S811(商品名）。 实施例 11
2D/3D显示-固相液晶微透镜阵列） " J. Harrold, D.j. Wilkes和 G. J. Woodgate"公开的方法 制作 2D/3D显示切换开关。 测试结果表明， 按实施例 1-10所制备的液晶介质， 具有有利的 Δη数值， 相对较高的 ΤΝ_,和相对较低的 V9oV1Q。由包含这些液品介质的 2D/3D显示间切换的液晶开关非常容易 得以控制。

Claims

权利要求
1. 一种用于 2D/3D显示切换开关的液晶介质， 包括：
基于所述液晶组合物总重量 20-99%的至少一种结构式 I 的化合物和基于所述液晶组 合物总重量 1-80%的至少一种结构式 Π的化合物，
Figure imgf000023_0001
Figure imgf000023_0002
其中，
R, > R2和 R3分别独立地表示未取代或被卤素至少单取代的具有 1-8个碳原子的烷基， 并且， 可选地， 所述烷基中的一个或多个不相邻的 -CH2-基团可被 -0-、 -S -、 -CH=CH -、 -CF=CF -、 -COO-、 -OCO-、 -OOC -、 -C≡C -、 3-5个碳原子的环垸烃所替代;
X 表示 F、 Cl、 CN、 SCF5、 NCS、 或者各自具有至多 4个碳原子的卤代烷基、 卤代 链烯基、 卤代垸氧基或卤代链烯氧基；
Z,、 Z2、 Z3、 Z4和 Z5 分别独立地表示单键、 -CH2CH2-、 -CF2CF2-、 -CF2CH2-、 -C CF2-、 -CH=CH -、 -CF=CF -、 -CF=CH -、 -CH=CF -、 -C≡C -、 -COO-、 -OCO-、 -CH20-、 -OCH2-、 -CF20-或 -OCF2-;
a、 b和 c 分别独立地表示 0、 1或 2， 其中， a+b≤2;
Figure imgf000023_0003
地表示未取代或被 1-4个氟原子取代的 1,4-亚环己基、 1,4-亚环己烯基或 1,4-亚环己二烯基， 并且， 可选地， 所述未取代或被取代的 1,4-亚环己基、 1,4-亚环己烯基或 1,4-亚环己二烯 基中的一个或两个彼此不相邻的 -CH2-基团可分别独立地被 -0-或 -S-替代； 或者 地表示 1,4-亚苯基， 并且， 可选地， 所述 1,4-亚苯基被一个或两个氟原子或氯原子取代， 可选地， 所述 1,4-亚苯基中一个或两个 -CH-基团被 N取代； 或者
A2 ) ~~ ~ ( A3 >— ~ < A4 >— ~ ( A5 — ~~ A6 >— ~~ A7 ,
分别独立 地表示 1，4-亚双环 [2.2.2]辛基、 萘 -2,6-二基、 反式-十氢化萘 -2，6-二基、 四氢化萘 -2,6-二基、 茚 -2，5-二基， 其中的一个或多个氢原子可以独立地被一个或多个卤原子取代。
2. 根据权利要求 1所述的液晶介质， 其特征在于 、 R2和 分别独立地表示具有 1-8个碳原子的垸基、 垸氧基或链烯基。
3. 根据权利要求 1所述的液晶介质， 其特征在于 X表示 OCF3、 F、 CI或 CN。
4. 根据权利要求 1所述的液晶介质， 其特征在于 Z,、 Z2、 ¾、 Z4和 Z5 分别独立地 表示单键、 -C≡C -或 -COO-。 根据权利要求 1的液晶介质， 其特征在于 地表
Figure imgf000024_0001
6. 根据权利要求 1 -5任一项所述的液晶介质，其特征在于所述结构式 I的化合物选自 通式 1-1到 1-20的至少一种化合物，
Figure imgf000024_0002
ίΖ
Figure imgf000025_0001
90ST00/Z10ZN3/X3d
Figure imgf000026_0001
其中， 、 R2如权利要求 1中所定义。
7. 根据权利要求 1-5任一项所述的液晶介质， 其特征在于所述结构式 Π的化合物选 自包括通式 II-1到 11-23的至少一种化合物，
Figure imgf000026_0002
Figure imgf000027_0001
Figure imgf000027_0002
25
Figure imgf000028_0001
Figure imgf000028_0002
其中， 如权利要求 1中所定义， L2彼此独立地表示 ^！或！^。
8. 根据权利要求 1所述的液晶介质， 其特征在于所述液晶组合物包含 40wt%-95wt% 结构式 I的化合物以及 5wt%-60wt%结构式 II的化合物。
9. 根据权利要求 1所述的液晶介质， 其特征在于所述液晶组合物包含 50wt%-85wt% 结构式 I的化合物以及 15wt%-50wt%结构式 II的化合物。
】0. —种 2D/3D显示切换开关， 包括如权利要求 1-9之一所述的液晶介质。
11 . 如权利要求 1-9之一所述的液晶介质在制备 2D/3D显示切换开关中的应用。
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