WO2013185437A1 - 超支化聚芳醚酮及其制备方法与应用、薄膜晶体管液晶显示器的基板 - Google Patents

超支化聚芳醚酮及其制备方法与应用、薄膜晶体管液晶显示器的基板 Download PDF

Info

Publication number
WO2013185437A1
WO2013185437A1 PCT/CN2012/085264 CN2012085264W WO2013185437A1 WO 2013185437 A1 WO2013185437 A1 WO 2013185437A1 CN 2012085264 W CN2012085264 W CN 2012085264W WO 2013185437 A1 WO2013185437 A1 WO 2013185437A1
Authority
WO
WIPO (PCT)
Prior art keywords
liquid crystal
polyaryletherketone
hyperbranched
hyperbranched polyaryletherketone
substrate
Prior art date
Application number
PCT/CN2012/085264
Other languages
English (en)
French (fr)
Inventor
严巍
Original Assignee
京东方科技集团股份有限公司
北京京东方显示技术有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 京东方科技集团股份有限公司, 北京京东方显示技术有限公司 filed Critical 京东方科技集团股份有限公司
Publication of WO2013185437A1 publication Critical patent/WO2013185437A1/zh

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C08G65/4018(I) or (II) containing halogens other than as leaving group (X)
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48Polymers modified by chemical after-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002Dendritic macromolecules
    • C08G83/005Hyperbranched macromolecules
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1337Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films

Definitions

  • the present disclosure relates to a hyperbranched polyaryletherketone, a preparation method and application thereof, a substrate of a thin film transistor liquid crystal display, and particularly to a hydroxyl terminated hyperbranched polyaryletherketone and a nitrile-terminated hyperbranched polyaryletherketone and preparation thereof Methods and applications. Background technique
  • the liquid crystal display requires that the liquid crystal molecules must be oriented in a certain direction when displaying a pattern under the action of an electric field.
  • the alignment film which coats the inner surface of the liquid crystal cell can be arranged in order, and the material which forms this film is a liquid crystal aligning film.
  • the materials used for liquid crystal alignment films in industrial production are all high molecular polymer materials, and most of them are linear polymer materials. Linear polymer polymers have solubility problems after too large molecular weight, and at the same time, they are anchored.
  • the liquid crystal molecules need to introduce as many functional groups as possible on the linear molecular backbone, resulting in high synthesis difficulty and high cost.
  • precursor polyamic acid materials are used, but the storage and use of polyamic acid are greatly affected by time and environment, which greatly restricts its practical application. The scope. Summary of the invention
  • An object of the present disclosure is to provide a hyperbranched polyaryletherketone which has good solubility, good film formability, and enhanced interaction with liquid crystal molecules.
  • hyperbranched polyaryletherketone comprising a compound of the formula: having a number average molecular weight of 27,500 to 45,000 and a molecular weight distribution of 1.45 to 1.84:
  • R is -OH or .
  • Another object of the present disclosure is to provide a process for preparing a hyperbranched polyaryletherketone.
  • Another aspect of the present disclosure provides a method of preparing a hyperbranched polyaryletherketone comprising the steps of:
  • the method of the hyperbranched polyaryletherketone of the present disclosure may further comprise reacting the hydroxy-terminated hyperbranched polyaryletherketone with 4-nitrophthalic acid to form a nitrile-terminated hyperbranched polyaryletherketone.
  • the 2,4',6-trifluoro-benzophenone is salted with the hydroquinone at 140-150 ° C for 2-2.5 hours, and heated to 170-220 ° C for 6-8 hours.
  • the 2,4',6-trifluoro-benzophenone is reacted with the hydroquinone in the presence of anhydrous potassium carbonate and N-mercaptopyrrolidone.
  • the hydroxy-terminated hyperbranched polyaryletherketone is reacted with the 4-nitrophthalic acid in the presence of anhydrous potassium carbonate and N,N-dimercaptoamide.
  • Still another aspect of the present disclosure relates to the use of the above-mentioned hyperbranched polyaryletherketone in the production of a liquid crystal alignment film.
  • TFT-LCD thin film transistor liquid crystal display
  • the substrate of the TFT-LCD provided by the present disclosure includes a liquid crystal alignment film comprising the above-described hyperbranched polyaryletherketone.
  • Hyper-branched polymers can be simply described as polymers with highly branched structures that differ from branched polymers and dendrimers. It is such a unique structure, It has a molecular motion different from that of a linear polymer, exhibiting a special property that many linear polymers do not have.
  • the hyperbranched polyaryletherketone of the present disclosure can provide a liquid crystal molecule and a liquid crystal alignment film by introducing a more reactive group with a liquid crystal molecule by introducing a ruthenium six-membered ring structure into the hyperbranched structure. The force between them.
  • the hyperbranched polyaryletherketone of the present disclosure has good solubility and good film formation.
  • the hydroxyl-terminated hyperbranched polyaryletherketone can be further functionalized to introduce a structure similar to a liquid crystal molecule such as a nitrile group, and to enhance the action on liquid crystal molecules.
  • Figure 1 is a graph showing the infrared characterization of the hydroxy-terminated hyperbranched polyaryletherketone of Example 1 and the nitrile-terminated hyperbranched polyaryletherketone of Example 3.
  • Figure 2 is a graph showing the infrared characterization of the hydroxy-terminated hyperbranched polyaryletherketone of Example 2.
  • Figure 3 is a graph showing the nuclear magnetic characterization of the hydroxy-terminated hyperbranched polyaryletherketone of Example 1 and the nitrile-terminated hyperbranched polyaryletherketone of Example 3.
  • Figure 4 is a graph showing the nuclear magnetic characterization of the hydroxy-terminated hyperbranched polyaryletherketone of Example 2.
  • the number average molecular weight of the hydroxyl-terminated hyperbranched polyaryletherketone is 27,500 45,000 and the molecular weight distribution is 1.45-1.84.
  • the infrared characterization results are shown in Fig. 1.
  • the nuclear magnetic characterization results are shown in Fig. 3.
  • the structural formula is:
  • reaction mixture is poured into acidic deionized water, washed with hot water to neutral under nitrogen atmosphere, and dried. Then, it was washed 3 times with ethanol under nitrogen atmosphere, filtered by hot, and dried to obtain a hyperbranched polyaryletherketone (OH-HPEEK) having a terminal group of a hydroxyl group.
  • OH-HPEEK hyperbranched polyaryletherketone
  • the number average molecular weight of the hydroxyl terminated hyperbranched polyaryletherketone is 27500 45000, and the molecular weight distribution is 1.45-1.84.
  • the infrared characterization results are shown in Fig. 2, and the nuclear magnetic characterization results are shown in Fig. 4.
  • the structural formula is as follows:
  • the number average molecular weight of the nitrile-terminated hyperbranched polyaryletherketone is 27,500 45,000 and the molecular weight distribution is 1.45-1.84.
  • the infrared characterization results are shown in Fig. 1.
  • the nucleus magnetic characterization results are shown in Fig. 3.
  • the structural formula is as follows:
  • Preparation Example 3 The obtained nitrile-terminated hyperbranched polyaryletherketone lg was dissolved in 10 ml of N-mercaptopyrrolidone (NMP) (AR, Tianjin Tiantai Fine Chemical Co., Ltd.) and stirred until it was completely Dissolved to obtain a hyperbranched polyaryletherketone dispersion, and the prepolymer dispersion was applied to a clean glass substrate (10 cm ⁇ 10 cm) by spin coating (model VTC-100, spin coating parameter: 1000 r/min).
  • NMP N-mercaptopyrrolidone
  • the specific heat treatment process is as follows: Under nitrogen conditions, 275 ° C 4h, 300 °C lh 325 °C lh, 350 ° C lh, 375 ° C 4h. The solvent was removed and film-formed to a thickness of 44 ⁇ m. The thickness of the film was observed by atomic force microscopy AFM.
  • the frame sealant is first cured with UV (ultraviolet light) for 60 seconds, then cured at 120 ° C for more than 1 hour to ensure that the frame sealant completely adheres the two glass substrates, and finally injects the liquid crystal (MAT- 09-1284 type, Merck liquid crystal company) 0.03mg, and again with a small amount of sealant seal and repeat the above steps of curing the sealant to make a complete liquid crystal analog device for testing.
  • UV ultraviolet
  • the liquid crystal MAT- 09-1284 type, Merck liquid crystal company
  • the pre-tilt test of the obtained liquid crystal analog devices was carried out, and the pretilt angles were 0.9°, 1.1°, 1.5 respectively. . 1.2. , with traditional STN type polyimide oriented film 2 ⁇ 5. The pretilt angle is greatly improved.
  • the hyperbranched polyaryletherketone of the present disclosure has good solubility, good film formability, and enhanced interaction with liquid crystal molecules, and is suitable for producing a liquid crystal alignment film.
  • the present disclosure also relates to the use of the above hyperbranched polyaryletherketone in the preparation of a liquid crystal alignment film.
  • the present disclosure also provides a substrate of a TFT-LCD comprising a liquid crystal alignment film comprising the above-described hyperbranched polyaryletherketone.
  • the substrate of the TFT-LCD may be an array substrate of a liquid crystal display or a color filter substrate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyethers (AREA)

Abstract

一种超支化聚芳醚酮及其制备方法与应用。超支化聚芳醚酮包含数均分子量27500〜45000、分子量分布1.45〜1.84的(I)通式化合物。其中,R为-OH或(II)、该超支化聚芳醚酮可以用于制备液晶取向膜。该超支化聚芳醚酮与液晶分子有更为相似的结构可以更好的提供液晶分子与液晶取向膜之间的作用力。

Description

超支化聚芳醚酮及其制备方法与应用、 薄膜晶体管液晶显示器的基板 技术领域
本公开涉及一种超支化聚芳醚酮及其制备方法与应用、 薄膜晶体管液晶 显示器的基板, 尤其涉及羟基封端超支化聚芳醚酮和腈基封端的超支化聚芳 醚酮及其制备方法与应用。 背景技术
液晶显示要求液晶分子在电场作用下显示图形时必须按照一定方向取 向。 能使液晶分子有序排列的是涂覆在液晶盒内表面的取向膜, 形成这种膜 的材料就是液晶取向膜。 现在工业生产上用作液晶取向膜的材料都是高分子 聚合物材料, 且绝大多数都是线性聚合物材料, 线性高分子聚合物在分子量 过大后会存在溶解性的问题, 同时为了锚定液晶分子需要在线性分子主链上 尽可能多的引入功能基团, 从而导致合成难度和成本较高。 为了改善聚酰亚 胺类取向膜材料的溶解性问题使用了前驱体聚酰胺酸材料, 但聚酰胺酸的保 存和使用都受时间和环境的影响很大,很大程度上制约了其实际应用的范围。 发明内容
本公开的一个目的是提供一种溶解性能良好, 成膜性好, 与液晶分子之 间的作用力增强的超支化聚芳醚酮。
本公开的一个方面所提供了一种超支化聚芳醚酮, 包含数均分子量 27500 ~ 45000、 分子量分布 1.45 ~ 1.84的下述通式化合物:
其中, R为 -OH或
Figure imgf000003_0001
本公开的另一个目的是提供一种制备超支化聚芳醚酮的方法。
本公开的另一个方面所提供了一种制备超支化聚芳醚酮的方法, 包括如 下步骤:
使 2,4 ',6-三氟-二苯酮与对苯二酚发生缩聚反应生成羟基封端超支化聚芳 醚酮; 所述 2,4',6-三氟 -二苯酮与所述对苯二酚的摩尔比 1 : ( 2.1-2.25 )。
例如本公开的超支化聚芳醚酮的方法, 还可以包括所述羟基封端超支化 聚芳醚酮与 4-硝基邻苯二腈反应生成腈基封端的超支化聚芳醚酮。
例如,所述 2,4',6-三氟 -二苯酮与所述对苯二酚在 140-150°C成盐 2-2.5小 时, 升温到 170-220 °C反应 6-8小时。
例如,所述 2,4',6-三氟 -二苯酮与所述对苯二酚在无水碳酸钾和 N-曱基吡 咯烷酮存在的条件下进行反应。
例如, 所述羟基封端超支化聚芳醚酮与所述 4-硝基邻苯二腈在无水碳酸 钾和 N, N-二曱基曱酰胺存在的条件下进行反应。
本公开的再一个方面还涉及上述的超支化聚芳醚酮在制备液晶取向膜中 的应用。
本公开的又一个目的是提供一种薄膜晶体管液晶显示器(TFT-LCD ) 的 基板。
本公开所提供的 TFT-LCD 的基板, 包括液晶取向膜, 该液晶取向膜包 括上述的超支化聚芳醚酮。
超支化聚合物(hyper-branched )可以简单的描述为具有高度支化结构的 聚合物, 它既与支化聚合物不同, 也与树形分子有别。正是这样独特的结构, 使其具有不同于线形聚合物的分子运动, 表现出许多线形聚合物所不具有的 特殊性能。 本公开的超支化聚芳醚酮, 由于在超支化结构中引入叛基六元环 结构, 而引入更多与液晶分子产生相互作用的基团, 可以更好的提供液晶分 子与液晶取向膜之间的作用力。 本公开的超支化聚芳醚酮溶解性能良好, 成 膜性好。
同时, 羟基封端的超支化聚芳醚酮还可以进一步功能化引入腈基等与液 晶分子相似的结构, 增强对液晶分子的作用力。 附图说明
为了更清楚地说明本公开实施例的技术方案, 下面将对实施例的附图作 简单地介绍,显而易见地,下面描述中的附图仅仅涉及本公开的一些实施例, 而非对本公开的限制。
图 1表示实施例 1的羟基封端超支化聚芳醚酮和实施例 3的腈基封端的 超支化聚芳醚酮的红外表征图谱。
图 2表示实施例 2的羟基封端超支化聚芳醚酮的红外表征图谱。
图 3表示实施例 1的羟基封端超支化聚芳醚酮和实施例 3的腈基封端的 超支化聚芳醚酮的核磁表征图谱。
图 4表示实施例 2的羟基封端超支化聚芳醚酮的核磁表征图谱。 具体实施方式
为使本公开实施例的目的、 技术方案和优点更加清楚, 下面将结合本公 开实施例的附图,对本公开实施例的技术方案进行清楚、 完整地描述。显然, 所描述的实施例是本公开的一部分实施例, 而不是全部的实施例。 基于所描 述的本公开的实施例, 本领域普通技术人员在无需创造性劳动的前提下所获 得的所有其他实施例, 都属于本公开保护的范围。
实施例 1. 羟基封端超支化聚芳醚酮的合成:
将 2.3619g ΒΒ2'型单体 2,4',6-三氟-二苯酮 (O.Olmol ), 2.3123g对苯二 酚( 0.021mol ), 3.312g无水碳酸钾( 0.024mol ), 25ml N-曱基吡咯烷酮( MP ), 10ml曱苯放入装有搅拌装置的 100ml三口瓶中, 通氮气、搅拌。 成盐温度控 制在 140°C 2-2.5小时, 逐步升温到 170°C反应 6-8小时, 降温后将反应混合 物倒入酸性去离子水中, 在氮气保护下用热水洗涤至中性, 干燥, 再在氮气 保护下用乙醇洗涤 3次, 热过滤, 干燥, 得到末端基为羟基封端的超支化聚 芳醚酮 (OH-HPEEK )。
羟基封端的超支化聚芳醚酮的数均分子量 27500 45000 , 分子量分布 1.45-1.84, 其红外表征结果如图 1所示, 核磁表征结果如图 3所示, 其结构 式为:
Figure imgf000005_0001
实施例 2. 羟基封端超支化聚芳醚酮的合成:
将 2.3619g ΒΒ2'型单体 2,4',6-三氟-二苯酮 (O.Olmol ), 2.4775g对苯二 酚( 0.0225mol ), 3.312g 无水碳酸钾( 0.024mol ), 25ml N-曱基吡咯烷酮 ( MP ), 10ml曱苯放入装有搅拌装置的 100ml三口瓶中, 通氮气、 搅拌。 成盐温度控制在 150°C 2-2.5小时, 逐步升温到 220°C反应 6-8小时, 降温后 将反应混合物倒入酸性去离子水中,在氮气保护下用热水洗涤至中性,干燥, 再在氮气保护下用乙醇洗涤 3次, 热过滤, 干燥, 得到末端基为羟基封端的 超超支化聚芳醚酮 (OH-HPEEK )。
羟基封端的超支化聚芳醚酮的数均分子量 27500 45000 , 分子量分布 1.45-1.84, 其红外表征结果如图 2所示, 核磁表征结果如图 4所示, 其结构 式如下:
Figure imgf000006_0001
实施例 3. 腈基封端的超支化聚芳醚酮
OH-HPEEK + CN-HPEEK
Figure imgf000006_0002
将 l.Og实施例 1的羟基封端的超支化聚芳醚酮, 0.69g 4-硝基邻苯二腈 ( 0.004mol ), 1.10g无水碳酸钾( 0.008mol ), 20ml N, N-二曱基曱酰胺(DMF ) 放入装有搅拌装置的 100ml三口瓶中, 通氮气, 室温搅拌 24小时以上。 将 反应混合物倒入去离子水中, 先用水洗至中性, 干燥, 再在氮气保护下用乙 醇洗涤 3次, 干燥, 得到腈基封端的超支化聚芳醚酮 (CN-HPEEK )。
腈基封端的超支化聚芳醚酮的数均分子量 27500 45000 , 分子量分布 1.45-1.84, 其红外表征结果如图 1所示, 核磁表征结果如图 3所示, 其结构 式如下:
Figure imgf000006_0003
性能分析:
( 1 )溶解性测试 在常温下在下述 10ml常规溶剂中加入 lg聚合物, 观察其溶解程度。 在常温下即可完全溶解表示 ++。
Figure imgf000007_0001
上述结果说明本公开的超支化聚芳醚酮溶解性能良好。
( 2 )成膜
准备实施例 3 所得的腈基封端的超支化聚芳醚酮 lg, 将其溶解于 10ml 的 N-曱基吡咯烷酮 (NMP) ( AR, 天津天泰精细化学品有限公司) 中, 搅拌直 至其完全溶解, 得到超支化聚芳醚酮分散液, 通过旋涂法 (MTI Spin coating, 型号 VTC-100, 旋涂参数: 1000r/分钟)将预聚物分散液涂布在清洁玻璃基板 ( lOcmX IOcm )上, 在真空烘箱内通过阶段升温, 具体的热处理过程如下: 在氮气条件下, 275°C 4h、 300 °C lh 325 °C lh 、 350°C lh 、 375°C 4h。 去 除溶剂并成膜, 其厚度为 44μπι。 通过原子力显微镜 AFM观察到膜的厚度均 匀。
( 3 ) 预倾角测试
制作液晶模拟器件: 由实施例 3腈基封端的超支化聚芳醚酮形成的液晶 取向膜的玻璃基板上, 各裁出 3cmx3cm的两块, 用摩擦机( M-2000型摩擦 机, 河北宣化试验机厂)对取向膜进行同向平行摩擦, 之后以使取向膜相对 的方式、 用封框胶(S-WB21 型, 积水化学株式会社) 沿玻璃基板的三边将 两块玻璃板粘接成盒, 对封框胶先使用 UV (紫外光) 固化 60秒钟, 然后在 120°C下热固化 1小时以上,保证封框胶将两玻璃基板完全粘牢,最后注入液 晶 (MAT-09-1284型, 默克液晶公司) 0.03mg, 并再次用少量封框胶封口并 重复上述固化封框胶的步骤, 制成一个完整可用于测试的液晶模拟器件。
釆用 PAT20型预倾角测试仪(长春联诚仪器有限公司)(测量误差为 ±0. 1° ), 分别对所得液晶模拟器件进行预倾角测试, 其预倾角分别为 0.9°、 1.1°、 1.5。、 1.2。, 与传统 STN型聚酰亚胺取向膜 2~5。的预倾角相比有很大改善。 综上所述, 本公开的超支化聚芳醚酮溶解性能良好, 成膜性好, 与液晶 分子的作用力增强, 适于制作液晶取向膜。
本公开还涉及上述的超支化聚芳醚酮在制备液晶取向膜中的应用。 本公开还提供 TFT-LCD 的基板, 其包括液晶取向膜, 该液晶取向膜包 括上述的超支化聚芳醚酮。 所述 TFT-LCD 的基板可以是液晶显示器的阵列 基板, 或者是彩膜基板。
以上所述仅是本公开的示范性实施方式, 而非用于限制本公开的保护范 围, 本公开的保护范围由所附的权利要求确定。

Claims

权利要求书
1. 一种超支化聚芳醚酮, 包含数均分子量 27500 ~ 45000、 分子量分布 1.45 ~ 1.84的下述通式化合物:
Figure imgf000009_0001
2. 一种制备超支化聚芳醚酮的方法, 包括如下步骤:
使 2,4 ',6-三氟-二苯酮与对苯二酚发生缩聚反应生成羟基封端超支化聚芳 醚酮;
所述 2,4',6-三氟 -二苯酮与所述对苯二酚的摩尔比 1 : ( 2.1-2.25 )。
3. 根据权利要求 2所述的方法,还包括所述羟基封端超支化聚芳醚酮与 4-硝基邻苯二腈反应生成腈基封端的超支化聚芳醚酮。
4. 根据权利要求 2或 3所述的方法, 其中, 所述 2,4',6-三氟 -二苯酮与所 述对苯二酚在 140-150 °C成盐 2-2.5小时, 升温到 170-220 °C反应 6-8小时。
5. 根据权利要求 2至 4中任一项所述的方法, 其中, 所述羟基封端超支 化聚芳醚酮与所述 4-硝基邻苯二腈在无水碳酸钾和 N, N-二曱基曱酰胺存在 的条件下进行反应。
6. 根据权利要求 2至 5中任一项所述的方法, 其中, 所述 2,4',6-三氟- 二苯酮与所述对苯二酚在无水碳酸钾和 N-曱基吡咯烷酮存在的条件下进行 反应。
7. 权利要求 1所述的超支化聚芳醚酮在制备液晶取向膜中的应用。
8. 一种薄膜晶体管液晶显示器(TFT-LCD ) 的基板, 包括液晶取向膜, 该液晶取向膜包括权利要求 1所述的超支化聚芳醚酮。
9. 权利要求 8所述的 TFT-LCD的基板, 该基板是液晶显示器的阵列基 板, 或者是彩膜基板。
PCT/CN2012/085264 2012-06-15 2012-11-26 超支化聚芳醚酮及其制备方法与应用、薄膜晶体管液晶显示器的基板 WO2013185437A1 (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201210202255.7 2012-06-15
CN201210202255.7A CN102731771B (zh) 2012-06-15 2012-06-15 超支化聚芳醚酮及其制备方法与应用

Publications (1)

Publication Number Publication Date
WO2013185437A1 true WO2013185437A1 (zh) 2013-12-19

Family

ID=46988132

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2012/085264 WO2013185437A1 (zh) 2012-06-15 2012-11-26 超支化聚芳醚酮及其制备方法与应用、薄膜晶体管液晶显示器的基板

Country Status (2)

Country Link
CN (1) CN102731771B (zh)
WO (1) WO2013185437A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020163777A1 (en) * 2019-02-08 2020-08-13 The University Of North Carolina At Chapel Hill Aromatic hyper branched polyaryletherketone-based membranes for high temperature gas separation

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102731771B (zh) * 2012-06-15 2014-06-04 京东方科技集团股份有限公司 超支化聚芳醚酮及其制备方法与应用
CN109810230A (zh) * 2019-02-18 2019-05-28 山东星火科学技术研究院 一种超支化磺化聚醚醚酮的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006267736A (ja) * 2005-03-24 2006-10-05 Fuji Xerox Co Ltd 非線形光学用ハイパーブランチポリマーおよびこれを含有する非線形光学用材料
CN101357985A (zh) * 2008-09-23 2009-02-04 吉林大学 超支化聚芳醚酮、其制备方法及在粘度调节剂方面的应用
TWI354579B (en) * 2006-12-29 2011-12-21 Ind Tech Res Inst An exchange membrane containing modified maleimide
CN102731771A (zh) * 2012-06-15 2012-10-17 京东方科技集团股份有限公司 超支化聚芳醚酮及其制备方法与应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006267736A (ja) * 2005-03-24 2006-10-05 Fuji Xerox Co Ltd 非線形光学用ハイパーブランチポリマーおよびこれを含有する非線形光学用材料
TWI354579B (en) * 2006-12-29 2011-12-21 Ind Tech Res Inst An exchange membrane containing modified maleimide
CN101357985A (zh) * 2008-09-23 2009-02-04 吉林大学 超支化聚芳醚酮、其制备方法及在粘度调节剂方面的应用
CN102731771A (zh) * 2012-06-15 2012-10-17 京东方科技集团股份有限公司 超支化聚芳醚酮及其制备方法与应用

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020163777A1 (en) * 2019-02-08 2020-08-13 The University Of North Carolina At Chapel Hill Aromatic hyper branched polyaryletherketone-based membranes for high temperature gas separation

Also Published As

Publication number Publication date
CN102731771A (zh) 2012-10-17
CN102731771B (zh) 2014-06-04

Similar Documents

Publication Publication Date Title
TWI375096B (zh)
JP5428336B2 (ja) 塗布液並びにそれを用いた液晶配向膜及び液晶表示素子
KR101616143B1 (ko) 액정 배향 처리제 및 그것을 사용한 액정 표시 소자, 그리고 신규한 디아민
CN104910106B (zh) 液晶取向剂、液晶取向膜、液晶显示元件及液晶显示元件的制造方法以及聚合性化合物
JP5061709B2 (ja) 液晶配向膜用組成物、液晶配向膜および液晶表示素子
US20140184997A1 (en) Prepolymer orientated film and method for preparing same, and liquid display device
CN102030901B (zh) 通过二酐和二胺反应获得的聚酰胺酸和聚酰亚胺
TWI637026B (zh) Liquid crystal alignment treatment agent and liquid crystal display element using same
KR101742838B1 (ko) 액정 배향 처리제 및 그것을 사용한 액정 표시 소자
EP1507161B1 (en) Liquid crystal aligning agent, liquid crystal aligning films and liquid crystal display devices
TW200527081A (en) Liquid crystal alignment treating agent for vertical alignment and liquid crystal display
JP2004117634A (ja) 液晶配向処理剤および液晶表示素子
JPWO2013081067A1 (ja) 液晶配向膜、液晶配向膜の製造方法、及び液晶表示素子
CN113544184B (zh) 膜形成用组合物、硬化膜、液晶取向膜及相位差膜
WO2002005024A1 (fr) Agent d'orientation de cristaux liquides et element d'affichage a cristaux liquides utilisant ce dernier
WO2013185437A1 (zh) 超支化聚芳醚酮及其制备方法与应用、薄膜晶体管液晶显示器的基板
TW201903130A (zh) 組成物、液晶配向劑、液晶配向膜及其製造方法、相位差板、偏光板及液晶元件
JP4752993B2 (ja) ポリイミド多孔質膜およびその製造法
WO2016158942A1 (ja) 液晶配向剤、液晶配向膜及び液晶表示素子
CN109970975B (zh) 一种高电压保持率型聚酰亚胺及其制备方法和应用
WO2018038160A1 (ja) 液晶配向剤、液晶配向膜及び液晶表示素子
WO2012157982A2 (ko) 디아민 화합물, 이의 제조방법, 액정 배향제, 액정 배향막 및 액정 표시 소자
TWI480314B (zh) 液晶配向劑、液晶配向膜及其液晶顯示元件
KR102096126B1 (ko) 액정 배향제, 액정 배향막 및 액정 표시 소자
KR101840484B1 (ko) 디아민 화합물, 액정 배향제 및 액정 표시 소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12878775

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1)EPC DATED 15.05.2015 (F1205A).

122 Ep: pct application non-entry in european phase

Ref document number: 12878775

Country of ref document: EP

Kind code of ref document: A1