WO2017075909A1 - 纯黑色染料、其制备方法以及电润湿显示油墨 - Google Patents

纯黑色染料、其制备方法以及电润湿显示油墨 Download PDF

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WO2017075909A1
WO2017075909A1 PCT/CN2016/070360 CN2016070360W WO2017075909A1 WO 2017075909 A1 WO2017075909 A1 WO 2017075909A1 CN 2016070360 W CN2016070360 W CN 2016070360W WO 2017075909 A1 WO2017075909 A1 WO 2017075909A1
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pure black
black dye
dye
pure
ink
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PCT/CN2016/070360
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French (fr)
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周国富
邓勇
郭媛媛
海耶斯·罗伯特·安德鲁
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深圳市国华光电科技有限公司
深圳市国华光电研究院
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Publication of WO2017075909A1 publication Critical patent/WO2017075909A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks

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  • This invention relates to ink materials, and more particularly to pure black dyes, methods for their preparation, and electrowetting display inks.
  • Electrowetting display (EFD, Electrofluide Display), also known as electrowetting display, is the first display developed by Philips in the Netherlands based on electrowetting display.
  • the display principle is to change the surface property of the hydrophobic layer by changing the voltage, and change the contact angle of the ink layer on the hydrophobic layer.
  • the ink uniformly wets the insulating layer to form a colored pixel;
  • the action of the electric field changes the surface properties of the hydrophobic layer to change the interfacial tension between the three phases of the ink-polar liquid-hydrophobic layer, and the ink is compressed to form a pixel point of a transparent or substrate background color, thereby obtaining a display image effect.
  • the single-layer electrowetting color display is realized by using black ink with color filter.
  • the multilayer electrowetting color display adopts red, green and blue.
  • the three primary colors are superimposed, the structure is complicated, and it is difficult to achieve saturated absorption of light by using three primary colors, and only gray can be obtained.
  • Patent publication number is TW201215645
  • the structure of the electrowetting black ink material based on the bisazo structure is reported in A1, but the dye is dark purple after verification by the author.
  • the technical problem to be solved by the present invention is to provide a pure black dye, a preparation method thereof, and an electrowetting display ink.
  • a method for preparing a pure black dye comprising the following steps:
  • the pure black ink obtained in the step (2) is purified and purified to obtain a pure black dye.
  • the mass ratio of the sulfur black dye, sodium sulfide, halogenated alkane is 1: (0.1-2): (0.5-10).
  • the sulfur black dye is at least one of water-soluble sulfur black, monosulfide black, and double sulfur black.
  • the halogenated alkane is a linear or branched halogenated alkane having 4 to 18 carbon atoms.
  • the linear or branched halogenated alkane having 4 to 18 carbon atoms is a linear or branched halogenated alkane having 4 to 18 carbon atoms, which is a chloro, bromo or iodo group. .
  • the solvent is a mixed solvent of water and an alcohol.
  • the step (3) is specifically: dissolving the pure black dye obtained in the step (2) in at least one of n-hexane, petroleum ether or toluene, filtering to remove insoluble impurities, drying and removing the solvent, and obtaining pure Black dye.
  • the present invention also provides a pure black dye prepared by the above preparation method.
  • the present invention also provides an electrowetting display ink obtained by dissolving the above-mentioned pure black dye in an organic solvent.
  • the organic solvent is at least one of n-decane, n-dodecane, and n-tetradecane.
  • the invention provides a pure black dye, a preparation method thereof and an electrowetting display ink, the preparation method of the pure black ink, comprising the steps of: taking a black sulfide dye, sodium sulfide, a halogenated alkane into a solvent, heating and refluxing; cooling The supernatant liquid was poured out to obtain a pure black ink; the obtained pure black ink was purified and purified to obtain a pure black dye.
  • the pure black dye is dissolved in an organic solvent to obtain an electrowetting display ink. Due to its complicated structure, the sulfur black dye has not been accurately analyzed for its composition, but it is recognized that its molecular structure contains a large amount of amino groups and hydroxyl groups.
  • the thiol-based and other modifiable groups utilizes a special structural design of the sulphur black dye to synthesize a pure black dye that satisfies the requirements of electrowetting display.
  • the prepared dye has a pure black color in a non-polar solvent n-decane. Solubility is as high as 100%.
  • Example 1 is a visible absorption spectrum of a pure black dye prepared in Example 1.
  • the invention provides a preparation method of a pure black dye, comprising the following steps: (1) taking a sulfur black dye, sodium sulfide, a halogenated alkane into a solvent, heating and refluxing; (2) cooling, pouring out the supernatant liquid, and obtaining Pure black ink; (3) Purifying and purifying the pure black ink obtained in the step (2) to obtain a pure black dye.
  • the mass ratio of the sulfur black dye, sodium sulfide, halogenated alkane is 1: (0.1-2): (0.5-10).
  • the sulfur black dye is at least one of water-soluble sulfur black, monosulfide black, and double sulfur black.
  • the halogenated alkane is a halogenated alkane having a linear or branched structure of 4 to 18 carbon atoms, and the linear or branched halogenated alkane having 4 to 18 carbon atoms is a chlorinated or brominated bromine.
  • the solvent is a mixed solvent of water and an alcohol, and the alcohol may be at least one of methanol, ethanol, n-propanol, and isopropanol, and the volume ratio of the water to the alcohol is 1: (0.5-2). .
  • the step (3) is specifically: dissolving the pure black dye obtained in the step (2) in at least one of n-hexane, petroleum ether or toluene, filtering to remove insoluble impurities, drying and removing the solvent to obtain a solid pure black dye. .
  • Dissolving the above pure black dye in an organic solvent gives an electrowetting display ink, which is also referred to as an electrowetting display ink.
  • the weight ratio of the pure black dye to the organic solvent is (1-50): (50-100), and the organic solvent may be an alkane such as n-decane, n-dodecane or n-tetradecane. At least one.
  • a water-soluble sulfur black solution having a chlorine content of 20% was weighed, and 1.0 g of sodium sulfide and 5 g of bromo-n-dodecane were dissolved in a mixed solvent of 20 mL of ethanol and 20 mL of water, and the mixture was heated under reflux for 24 hours. The solution was cooled, the supernatant was decanted, the bottom pure black ink was taken out, dissolved in 50 mL of petroleum ether, and the insoluble impurities were removed by filtration, and the filtrate was evaporated to dryness to remove the solvent to obtain 4 g of a solid black dye Dye-1. The above pure black dye was dissolved in 5 mL of n-decane to obtain an electrowetting black ink material K-1.
  • the solution was cooled, the supernatant was decanted, the bottom pure black ink was taken out, dissolved in 50 mL of toluene, and the insoluble impurities were removed by filtration, and the filtrate was evaporated to dryness to remove the solvent to obtain 3.8 g of solid pure black dye Dye-3, and 1 g of the above pure
  • the black dye was dissolved in 5 mL of n-decane to obtain an electrowetting black ink material K-3.
  • Example 1 The pure black dye Dye-1 obtained in Example 1 was subjected to spectral analysis to obtain Fig. 1.
  • the electrowetting black ink materials prepared in Examples 1-5 were tested for performance. The test results are shown in Table 1.
  • the solubility in the table is 100%, which means that the solubility of the dye in n-decane is 100%. N-tetradecane can be miscible in any ratio.
  • the synthesized black ink material has a FoM value of up to 8699, and the prepared black ink has a very high saturation and can be applied to prepare an electrowetting display electronic paper with high contrast. .

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

本发明公开了纯黑色油墨染料、其制备方法以及电润湿显示油墨，所述纯黑色油墨的制备方法，包括以下步骤：取硫化黑染料、硫化钠、卤代烷烃加入溶剂中，加热回流反应；冷却，倒出上层清液，得到纯黑色油墨；将所述纯黑色油墨溶于有机溶剂即可得到电润湿显示油墨，硫化黑染料由于其结构复杂，至今都未有人能准确分析其成分，但公认为其分子结构中含有大量氨基、羟基、巯基等可改性基团，本发明利用硫化黑染料特殊的结构设计合成出了满足电润湿显示要求的纯黑色油墨染料，所制备的油墨染料具有纯正的黑色，在非极性溶剂正十烷中溶解度高达100%。

Description

纯黑色染料、其制备方法以及电润湿显示油墨
技术领域
本发明涉及油墨材料，尤其涉及纯黑色染料、其制备方法以及电润湿显示油墨。
背景技术
电润湿显示器（EFD，Electrofluide display），也称为电湿润显示器，是荷兰飞利浦公司于2003年首次研制出的以电润湿显示为原理的显示器。该显示原理是利用改变电压从而控制疏水层的表面性能，改变油墨层在疏水层上的接触角，在未加电压时，油墨对绝缘层均匀润湿，形成一个有色像素点；施加电压时，电场的作用改变了疏水层的表面性能使油墨-极性液体-疏水层三相之间的界面张力发生变化，油墨被压缩，形成透明或基板底色的像素点，从而获得显示图像效果。
为了实现彩色电润湿显示，荷兰Liquvista公司提出了两种可能的结构模型：单层或多层结构。单层电润湿彩色显示采用黑色油墨搭配彩色滤光片实现，为了达到较高的色彩对比度，需要配制色光纯正、溶解度极高的黑色油墨材料；而多层电润湿彩色显示采用红绿蓝三基色的叠加而成，结构复杂，且采用三基色难以达到对光的饱和吸收，仅能得到灰色。
不管是开发具有单层结构的彩色电润湿显示器，还是开发具有高对比度的黑白单色电润湿显示器，为了达到反射率高于50%，对比度高于15的显示效果，具有高FoM的纯黑色电润湿油墨材料都必不可少，因此，合成满足电润湿要求的黑色油墨材料成为了研究热点与难点。
具有纯正黑色的发色体系极少，因此，目前针对电润湿显示黑色油墨材料的研究报道数量较少。专利公开编号为TW201215645 A1中报道了基于双偶氮结构的电润湿黑色油墨材料结构，但经过作者验证，该染料实为暗紫色。
发明内容
本发明所要解决的技术问题是提供纯黑色染料、其制备方法以及电润湿显示油墨。
本发明所采取的技术方案是：
一种纯黑色染料的制备方法，包括以下步骤：
（1）取硫化黑染料、硫化钠、卤代烷烃加入溶剂中，加热回流反应；
（2）冷却，倒出上层清液，得到纯黑色油墨；
（3）将所述步骤（2）所得的纯黑色油墨提纯精制，得到纯黑色染料。
优选地，所述硫化黑染料、硫化钠、卤代烷烃的质量比1：（0.1-2）：（0.5-10）。
优选地，所述硫化黑染料为水溶性硫化黑、单倍硫化黑、双倍硫化黑中的至少一种。
优选地，所述卤代烷烃为碳原子数为4-18的直链或支链结构的卤代烷烃。
进一步优选地，所述碳原子数为4-18的直链或支链结构的卤代烷烃为氯代、溴代、碘代的碳原子数为4-18的直链或支链结构的卤代烷烃。
优选地，所述溶剂为水和醇类的混合溶剂。
优选地，所述步骤（3）具体为：将所述步骤（2）得到的纯黑色染料溶于正己烷、石油醚或甲苯中的至少一种，过滤除去不溶性杂质，干燥除去溶剂，得到纯黑色染料。
本发明还提供了一种由上述的制备方法制备得到的纯黑色染料。
本发明还提供了一种电润湿显示油墨，由上述的纯黑色染料溶于有机溶剂中得到。
优选地，所述有机溶剂为正十烷、正十二烷、正十四烷中的至少一种。
本发明的有益效果是：
本发明提供了纯黑色染料、其制备方法以及电润湿显示油墨，所述纯黑色油墨的制备方法，包括以下步骤：取硫化黑染料、硫化钠、卤代烷烃加入溶剂中，加热回流反应；冷却，倒出上层清液，得到纯黑色油墨；将所得的纯黑色油墨提纯精制，得到纯黑色染料。将所述纯黑色染料溶于有机溶剂即可得到电润湿显示油墨，硫化黑染料由于其结构复杂，至今都未有人能准确分析其成分，但公认为其分子结构中含有大量氨基、羟基、巯基等可改性基团，本发明利用硫化黑染料特殊的结构设计合成出了满足电润湿显示要求的纯黑色染料，所制备的染料具有纯正的黑色，在非极性溶剂正十烷中溶解度高达100%。
附图说明
图1为实施例1制备得到的纯黑色染料的可见吸收光谱图。
具体实施方式
以下将结合实施例和附图对本发明的构思、具体结构及产生的技术效果进行清楚、完整地描述，以充分地理解本发明的目的、特征和效果。显然，所描述的实施例只是本发明的一部分实施例，而不是全部实施例，基于本发明的实施例，本领域的技术人员在不付出创造性劳动的前提下所获得的其他实施例，均属于本发明保护的范围。另外，专利中涉及到的所有联接/连接关系，并非单指构件直接相接，而是指可根据具体实施情况，通过添加或减少联接辅件，来组成更优的联接结构。本发明创造中的各个技术特征，在不互相矛盾冲突的前提下可以交互组合。
本发明提供了一种纯黑色染料的制备方法，包括以下步骤：（1）取硫化黑染料、硫化钠、卤代烷烃加入溶剂中，加热回流反应；（2）冷却，倒出上层清液，得到纯黑色油墨；（3）将所述步骤（2）所得的纯黑色油墨提纯精制，得到纯黑色染料。所述硫化黑染料、硫化钠、卤代烷烃的质量比1：（0.1-2）：（0.5-10）。所述硫化黑染料为水溶性硫化黑、单倍硫化黑、双倍硫化黑中的至少一种。所述卤代烷烃为卤代烷烃为碳原子数为4-18的直链或支链结构的卤代烷烃，所述碳原子数为4-18的直链或支链结构的卤代烷烃为氯代、溴代、碘代的碳原子数为4-18的直链或支链结构的卤代烷烃。所述溶剂为水和醇类的混合溶剂，所述醇可以为甲醇、乙醇、正丙醇、异丙醇中的至少一种，所述水和醇的体积比为1：（0.5-2）。所述步骤（3）具体为：将所述步骤（2）得到的纯黑色染料溶于正己烷、石油醚或甲苯中的至少一种，过滤除去不溶性杂质，干燥除去溶剂，得到固体纯黑色染料。将上述纯黑色染料溶于有机溶剂中可以得到一种电润湿显示油墨，所述电润湿显示油墨也称为电湿润显示油墨。所述纯黑色染料与所述有机溶剂重量比为（1-50）：（50-100），所述有机溶剂可为烷烃，如正十烷、正十二烷、正十四烷中的的至少一种。
实施例1：
量取10 mL含量为20%的水溶性硫化黑溶液，称取1.0g硫化钠、5g溴代正十二烷溶于20mL乙醇和20mL水的混合溶剂中，加热回流反应24h。将溶液冷却，倒去上层清液，取出底部纯黑色油墨，用50mL石油醚溶解后过滤除去不溶性杂质，取滤液旋蒸、干燥除去溶剂，得4g固体纯黑色染料Dye-1，取1g 上述纯黑色染料溶于5mL正十烷中，得到电润湿黑色油墨材料K-1。
实施例2：
称取2g力份为100%的单倍硫化黑、1.5g硫化钠、5g溴代正辛烷溶于20mL乙醇和20mL水的混合溶剂中，加热回流反应24h。将溶液冷却，倒去上层清液，取出底部纯黑色油墨，用50mL石油醚溶解后过滤除去不溶性杂质，取滤液旋蒸、干燥除去溶剂，得2.9g固体纯黑色染料Dye-2，取1g上述纯黑色染料溶于5mL正十烷中，得到电润湿黑色油墨材料K-2。
实施例3：
称取1g力份为200%的双倍硫化黑、2.0g硫化钠、5g溴代异辛烷溶于20mL甲醇和20mL水的混合溶剂中，加热回流反应24h。将溶液冷却，倒去上层清液，取出底部纯黑色油墨，用50mL甲苯溶解后过滤除去不溶性杂质，取滤液旋蒸、干燥除去溶剂，得3.8g固体纯黑色染料Dye-3，取1g上述纯黑色染料溶于5mL正十烷中，得到电润湿黑色油墨材料K-3。
实施例4：
称取1g力份为200%的双倍硫化黑、0.1g硫化钠、0.5g溴代异辛烷溶于20mL正丙醇和10mL水的混合溶剂中，加热回流反应24h。将溶液冷却，倒去上层清液，取出底部纯黑色油墨，用50mL正己烷溶解后过滤除去不溶性杂质，取滤液旋蒸、干燥除去溶剂，得1.2g固体纯黑色染料Dye-4，取1g上述纯黑色染料溶于5mL正十二烷中，得到电润湿黑色油墨材料K-4。
实施例5：
称取1g力份为200%的双倍硫化黑、2g硫化钠、10g溴代异辛烷溶于20mL异丙醇和40mL水的混合溶剂中，加热回流反应24h。将溶液冷却，倒去上层清液，取出底部纯黑色油墨，用50mL正己烷溶解后过滤除去不溶性杂质，取滤液旋蒸、干燥除去溶剂，得4.2g固体纯黑色染料Dye-5，取2g上述纯黑色染料溶于5mL正十烷中，得到电润湿黑色油墨材料K-5。
对实施例1制备所得的纯黑色染料Dye-1进行光谱分析，得到图1。对实施例1-5制备所得的电润湿黑色油墨材料进行性能测试，得到测试结果如表1，表格中所述溶解度为100%，是指染料在正十烷中溶解度为100%，染料与正十四烷可以以任意比例混溶。
表1 所制备的三种电润湿黑色油墨材料测试
油墨名称 溶解度 最大吸收波长/nm 半峰宽/nm 摩尔消光系数 FoM 颜色
K-1 100% 580 >400 5108 3147 纯黑色
K-2 100% 580 >400 11188 8699 纯黑色
K-3 100% 580 >400 7073 4358 纯黑色
K-4 100% 580 >400 8654 7563 纯黑色
K-5 100% 580 >400 6654 5347 纯黑色
从表1中可以看出，所合成的黑色油墨材料的FoM值最高可达8699，所配制得到的黑色油墨具有非常高的饱和度，可应用于制备具有较高对比度的电润湿显示电子纸。

Claims (10)

  1. 一种纯黑色染料的制备方法，其特征在于，包括以下步骤：
    （1）取硫化黑染料、硫化钠、卤代烷烃加入溶剂中，加热回流反应；
    （2）冷却，倒出上层清液，得到纯黑色油墨；
    （3）将所述步骤（2）所得的纯黑色油墨提纯精制，得到纯黑色染料。
  2. 根据权利要求1所述的纯黑色染料的制备方法，其特征在于，所述硫化黑染料、硫化钠、卤代烷烃的质量比1：（0.1-2）：（0.5-10）。
  3. 根据权利要求1所述的纯黑色染料的制备方法，其特征在于，所述硫化黑染料为水溶性硫化黑、单倍硫化黑、双倍硫化黑中的至少一种。
  4. 根据权利要求1所述的纯黑色染料的制备方法，其特征在于，所述卤代烷烃为碳原子数为4-18的直链或支链结构的卤代烷烃。
  5. 根据权利要求4所述的纯黑色染料的制备方法，其特征在于，所述碳原子数为4-18的直链或支链结构的卤代烷烃为氯代、溴代、碘代的碳原子数为4-18的直链或支链结构的卤代烷烃。
  6. 根据权利要求1所述的纯黑色染料的制备方法，其特征在于，所述溶剂为水和醇类的混合溶剂。
  7. 根据权利要求1所述的纯黑色染料的制备方法，其特征在于，所述步骤（3）具体为：将所述步骤（2）得到的纯黑色染料溶于正己烷、石油醚或甲苯中的至少一种，过滤除去不溶性杂质，干燥除去溶剂，得到纯黑色染料。
  8. 一种由权利要求1-7任一项所述的制备方法制备得到的纯黑色染料。
  9. 一种电润湿显示油墨，其特征在于，由权利要求8所述的纯黑色染料溶于有机溶剂中得到。
  10. 根据权利要求9所述的电润湿显示油墨，其特征在于，所述有机溶剂为正十烷、正十二烷、正十四烷中的至少一种。
PCT/CN2016/070360 2015-11-02 2016-01-07 纯黑色染料、其制备方法以及电润湿显示油墨 WO2017075909A1 (zh)

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