WO2021031359A1 - 聚合物薄膜及其制备方法、柔性折叠面板 - Google Patents

聚合物薄膜及其制备方法、柔性折叠面板 Download PDF

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WO2021031359A1
WO2021031359A1 PCT/CN2019/115440 CN2019115440W WO2021031359A1 WO 2021031359 A1 WO2021031359 A1 WO 2021031359A1 CN 2019115440 W CN2019115440 W CN 2019115440W WO 2021031359 A1 WO2021031359 A1 WO 2021031359A1
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polymer
flask
polymer film
bis
preparing
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French (fr)
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赵远
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武汉华星光电半导体显示技术有限公司
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Priority to US16/624,149 priority Critical patent/US11479632B2/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/341—Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • C08G69/28—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2377/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2475/04—Polyurethanes
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • G09F9/301—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements flexible foldable or roll-able electronic displays, e.g. thin LCD, OLED

Definitions

  • the present disclosure relates to the field of display technology, in particular to a polymer film, a preparation method thereof, and a flexible folding panel.
  • OLED Organic Light-Emitting Device
  • the foldable OLED display is one of the current research hotspots.
  • the cover plate on the surface plays an important protective role. Therefore, the hardness of the screen surface will directly determine the safety of the screen.
  • the cover plate also needs to have good bending and recovery performance.
  • the surface hardness of the material Larger but poorer bending performance, or better bending performance but low surface hardness, resulting in poor quality and overall performance of the display panel.
  • the surface hardness of the existing OLED display screen and the cover plate of the display screen cannot match well with its bending performance after adding polymer.
  • the foldability cannot be balanced with each other, and the quality of the display screen and the overall performance are poor.
  • the present disclosure provides a polymer film, a preparation method thereof, and a flexible folding panel, so as to solve the problem that the surface hardness and bending performance of the existing OLED display screen and the cover plate of the display screen cannot be affected by polymer addition. It is well matched. In actual products, there are problems such as the surface hardness and bending properties of the materials cannot be balanced with each other, and the quality of the display screen and the overall performance are poor.
  • a method for preparing a polymer film including the following steps:
  • the polymer monomer includes: N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(4-hexylnaphthalene-1-amine) or N,N '-(Methylenebis(6-isocyanato-3,1-phenylene))bis(10-octylanthracene-9-amine);
  • the chemical structural formula of the polymer is:
  • the additive includes 4-hexylnaphthylamine.
  • the step S100 further includes the following steps:
  • the step S201 further includes the following steps:
  • the step S300 includes: passing argon into the flask and adding dilute hydrochloric acid.
  • the additive includes 10-amino-9-octylanthracene.
  • the step S100 further includes the following steps:
  • the step S400 further includes: adding cesium carbonate, cuprous iodide, and 18-crown-6 into the flask.
  • the step S201 further includes the following steps:
  • a polymer film including:
  • the reinforcing layer is provided on the substrate, the reinforcing layer includes a polymer, the side chain of the polymer includes a plurality of rigid segments and a plurality of flexible segments, the rigid segments and the The flexible segment modifies and strengthens the side chain of the polymer.
  • the chemical structural formula of the polymer is:
  • the chemical structural formula of the polymer is:
  • a method for preparing a polymer film including the following steps:
  • the polymer monomer includes: N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(4-hexylnaphthalene-1) -Amine) or N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(10-octylanthracene-9-amine).
  • the additive includes 4-hexylnaphthylamine
  • the step S100 further includes the following steps:
  • the step S201 further includes the following steps:
  • the additive includes 10-amino-9-octylanthracene
  • the step S100 further includes the following steps:
  • the step S201 further includes the following steps:
  • the present disclosure provides a polymer film, a preparation method, and a flexible folding panel.
  • the side chains of the polymer structure include rigid and flexible segments in different proportions.
  • the chain segment and the flexible chain segment modify the side chains of the polymer, strengthen the mechanical properties of the hardened layer, improve the surface hardness and friction resistance of the hardened layer, and improve the bending performance of the flexible folding panel.
  • FIG. 1 is a schematic diagram of the structure of a polymer film according to an embodiment of the disclosure
  • FIG. 3 is a schematic diagram of the structure of a flexible folding panel provided by an embodiment of the disclosure.
  • FIG. 1 is a schematic diagram of the structure of a polymer film according to an embodiment of the disclosure.
  • the polymer film includes a substrate 100 and a strengthening layer 101.
  • the reinforcement layer 101 is disposed on the substrate 100, wherein the reinforcement layer 101 further includes a polymer, and the reinforcement layer 101 is composed of the polymer.
  • the polymer is A, and its structural formula is:
  • the polymer is B, and its structural formula is:
  • the side chain of the molecular structural formula of the polymer includes a plurality of rigid segments and a plurality of flexible segments.
  • the rigid and flexible segments act on the side chains of the polymer and modify the side chains of the polymer. So as to achieve the purpose of strengthening.
  • the polymer provided by the embodiments of the present disclosure strengthens the film layer by introducing different rigid and flexible segments into the side chains and adjusting the ratio of the two to meet the requirements of flexible foldable display screens.
  • the embodiment of the disclosure provides a method for preparing a polymer film, as shown in FIG. 2, which is a flow chart of the preparation process of the polymer film according to the embodiment of the disclosure.
  • the preparation process includes the following steps:
  • step S100 the monomers of the polymer are mainly prepared to prepare for subsequent polymer preparation.
  • step S100 Through the polymer monomer obtained in step S100, and a series of chemical synthesis reactions are carried out, the polymer of the embodiment of the present disclosure is finally prepared.
  • the prepared polymer is coated on the substrate and dried to form a film to form a reinforced film covering the board.
  • the monomers of the polymer include: N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(4-hexyl) Naphthalene-1-amine) or N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(10-octylanthracene-9-amine).
  • the monomer chemical formula of polymer A is C 47 H 48 N 4 O 2 , that is, N,N'-(methylenebis(6-isocyanato-3,1 -Phenylene)) bis(4-hexylnaphthalene-1-amine).
  • Polymer A is synthesized from the monomers of polymer A through a series of reactions. Specifically, the monomer of polymer A is synthesized first, and the synthesis process is as follows:
  • the additives are cesium carbonate (4.62g, 24mmol), cuprous iodide (228mg, 1.2mmol) and 18-crown-6 (104mg, 0.4mmol);
  • the flask is pumped three times, and the protective gas argon is filled into the flask.
  • 50 mL of deoxygenated N,N-dimethylpropenylurea (DMPU) is added. Then, the mixture is placed at 180°C for 24 hours. ;
  • the contents in the flask were cooled to room temperature, the mixture was poured into 100 ml of ice water, extracted with dichloromethane three times, the organic phases were combined, silica gel was added, the solvent was removed, and the separation was carried out by column chromatography.
  • the separated liquid was dichloromethane And n-hexane, the volume ratio of the two is 1:1 to obtain 4.2 g of white solid.
  • the yield of the white solid is 60%, which is higher than that in the existing production process.
  • the nuclear magnetic detection of the white solid substance is consistent with the chemical formula of the monomer of polymer A.
  • the polymer is prepared from the monomer A.
  • the specific steps are as follows:
  • the monomer of polymer A that is, N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(4-hexylnaphthalene-1-amine)( 4.2g, 6mmol) and oxalic acid (0.558g, 6.2mmol) were added to a 25ml round bottom flask;
  • the weight average molecular weight of the polymer is 2356 kg/mol, the number average molecular weight is 1980 kg/mol, and the degree of dispersion is 1.83.
  • polymer B when the polymer is B, during the synthesis process, polymer B is prepared from the monomers of polymer B through a series of chemical synthesis.
  • the chemical formula of the monomers of polymer B is C 59 H 60 N 4 O 2 , namely N,N'-(methylenebis(6-isocyanato-3,1-phenylene))bis(10-octylanthracene-9-amine).
  • Polymer B is synthesized from the monomers of polymer B through a series of reactions. Specifically, the monomer of polymer B is synthesized first, and the synthesis process is as follows:
  • the additives are cesium carbonate (4.62g, 24mmol), cuprous iodide (228mg, 1.2mmol) and 18-crown-6 (104mg, 0.4mmol);
  • DMPU deoxygenated N,N-dimethylpropenylurea
  • the nuclear magnetic detection of the white solid substance is consistent with the chemical formula of the monomer of polymer B.
  • the polymer is prepared from the monomer B.
  • the specific steps include the following:
  • the mass of the obtained white solid was 3.07 g, and the yield was 68%.
  • the weight average molecular weight of polymer B was 2578 kg/mol, the number average molecular weight was 2043 kg/mol, and the degree of dispersion was 1.79.
  • reaction of synthesizing polymer B from monomers is as follows:
  • the polymer film provided in the embodiment of the present disclosure is prepared. It is coated on the cover plate, when polymer A is used as the hardened layer, coated on the transparent polyimide, the surface hardness of the cover plate is 2H; when the polymer B is used as the hardened layer, it is coated on the transparent polyimide.
  • the surface hardness of the cover plate obtained on the imide is 3H. The hardness of the hardened layer is improved, and also has good bending performance and anti-friction performance.
  • the embodiment of the present disclosure also provides a flexible folding panel, as shown in FIG. 3, which is the flexible folding panel provided by the embodiment of the disclosure.
  • the flexible folding panel 300 is provided with the polymer film 301 provided in the embodiment of the present disclosure, and the polymer film 301 is prepared by the preparation method in the embodiment of the present disclosure.

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Abstract

提供一种聚合物薄膜及其制备方法。聚合物薄膜包括衬底和强化层，强化层包括聚合物，聚合物的侧链包括多个刚性链段和柔性链段，刚性链段和柔性链段对聚合物的侧链进行修饰强化，聚合物由聚合物的单体通过一系列的反应合成，聚合物薄膜强化了面板覆盖板的硬度并提高了抗摩擦性能和弯折性能。

Description

聚合物薄膜及其制备方法、柔性折叠面板 技术领域
本揭示涉及显示技术领域，尤其涉及一种聚合物薄膜及其制备方法、柔性折叠面板。
背景技术
有机电致发光显示器件(Organic Light-Emitting Device，OLED)相对于液晶显示装置具有自发光、反应快、轻薄等优点，已成为显示领域的新兴技术。
可折叠的OLED显示屏是目前研究的热点之一，在可折叠的显示屏幕中，位于表面的覆盖板起到了很重要的保护作用，因此，屏幕表面硬度的高低将直接决定屏幕的安全。
但是，由于可折叠设备的需求，覆盖板还需要具有良好的弯折和恢复性能，为了提高覆盖板的性能，需要在覆盖板表面添加或涂布聚合物材料，通过添加的聚合物材料来达到提高现有的覆盖板的表面硬度以及弯折性能，但是的聚合物在涂布到覆盖板以及显示屏幕后，其覆盖板的表面硬度与弯折性不能很好的相匹配，材料的表面硬度较大但是其弯折性较差，或者弯折性能较好但是其表面硬度又不高，造成显示面板的质量以及综合性能较差。
因此需要对现有技术中的问题提出解决方法。
技术问题
综上所述，现有的OLED显示屏幕以及显示屏幕的覆盖板在添加聚合物后，其表面硬度与其弯折性能不能很好的相匹配，在实际产 品中，存在着材料的表面硬度以及弯折性不能相互平衡，显示屏幕的质量以及综合性能差等问题。针对上述问题，需要提出进一步的解决和完善方案。
技术解决方案
为解决上述问题，本揭示提供一种聚合物薄膜及其制备方法、柔性折叠面板，以解决现有的OLED显示屏幕以及显示屏幕的覆盖板在添加聚合物后，其表面硬度与其弯折性能不能很好的相匹配，在实际产品中，存在着材料的表面硬度以及弯折性不能相互平衡，显示屏幕的质量以及综合性能差等问题。
为解决上述技术问题，本揭示实施例提供的技术方案如下：
根据本揭示实施例的第一方面，提供了一种聚合物薄膜的制备方法，包括如下步骤：
S100：将双(3-溴-4-异氰酸根合苯基)甲烷与添加物混合反应，并制备聚合物单体；
S101：将所述聚合物单体与乙二酸反应，制备聚合物；
S102：将所述聚合物涂布在衬底上，形成聚合物薄膜。
所述聚合物单体包括：N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)或N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)；
所述聚合物的化学结构式为：
Figure PCTCN2019115440-appb-000001
根据本揭示一实施例，所述添加物包括4-己基萘胺。
根据本揭示一实施例，所述步骤S100中，还包括如下步骤：
S200：将双(3-溴-4-异氰酸根合苯基)甲烷和4-己基萘胺加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
S201：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲，以形成混合物，将所述混合物置于180℃反应24小时；
S202：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
根据本揭示一实施例，所述步骤S201中还包括如下步骤：
S300：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)和乙二酸混合加入烧瓶中，于80℃反应12小时；
S301：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
根据本揭示一实施例，所述步骤S300中包括：在所述烧瓶中通入氩气，并加入稀盐酸。
根据本揭示一实施例，所述添加物包括10-氨基-9-辛基蒽。
根据本揭示一实施例，所述步骤S100中还包括如下步骤：
S400：将双(3-溴-4-异氰酸根合苯基)甲烷和10-氨基-9-辛基蒽加入烧瓶中；
S401：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,混合物置于180℃反应24小时；
S402：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
根据本揭示一实施例，所述步骤S400中，还包括：在所述烧瓶中加入碳酸铯、碘化亚铜以及18-冠-6。
根据本揭示一实施例，所述步骤S201中还包括如下步骤：
S500：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
S501：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
根据本揭示实施例的第二方面，提供一种聚合物薄膜，包括：
衬底；以及
强化层；
其中，所述强化层设置在所述衬底上，所述强化层包括聚合物，所述聚合物的侧链包括多个刚性链段和多个柔性链段，所述刚性链段 和所述柔性链段对所述聚合物的所述侧链进行修饰强化。
根据本揭示一实施例，所述聚合物的化学结构式为：
Figure PCTCN2019115440-appb-000002
根据本揭示一实施例，所述聚合物的化学结构式为：
Figure PCTCN2019115440-appb-000003
根据本揭示的第三方面，还提供一种聚合物薄膜的制备方法，包括如下步骤：
S100：将双(3-溴-4-异氰酸根合苯基)甲烷与添加物混合反应，并制备聚合物单体；
S101：将所述聚合物单体与乙二酸反应，制备聚合物；
S102：将所述聚合物涂布在衬底上，形成聚合物薄膜。
根据本揭示一实施例，所述聚合物单体包括：N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)或N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)。
根据本揭示一实施例，所述添加物包括4-己基萘胺，所述步骤S100中，还包括如下步骤：
S200：将双(3-溴-4-异氰酸根合苯基)甲烷和4-己基萘胺加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
S201：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,以形成混合物，将所述混合物置于180℃反应24小时；
S202：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
根据本揭示一实施例，所述步骤S201中还包括如下步骤：
S300：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
S301：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
根据本揭示一实施例，所述添加物包括10-氨基-9-辛基蒽，所述步骤S100中还包括如下步骤：
S400：将双(3-溴-4-异氰酸根合苯基)甲烷和10-氨基-9-辛基蒽加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
S401：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,混合物置于180℃反应24小时；
S402：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
根据本揭示一实施例，所述步骤S201中还包括如下步骤：
S500：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
S501：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
有益效果
综上所述，本揭示实施例的有益效果为：
本揭示提供一种聚合物薄膜及制备方法、柔性折叠面板，通过在硬化层上涂布聚合物，所述聚合物结构的侧链中，包括有不同比例的刚性链段和柔性链段，刚性链段和柔性链段对聚合物的侧链进行修饰，并强化硬化层的力学性能，提高了硬化层的表面硬度和抗摩擦性能，提高柔性折叠面板的弯折性能。
附图说明
图1为本揭示实施例的聚合物薄膜结构示意图；
图2为本揭示实施例的聚合物薄膜的制备工艺流程图；
图3为本揭示实施例提供的柔性折叠面板结构示意图。
本发明的最佳实施方式
以下各实施例的说明是参考附加的图式，用以例示本揭示可用以实施的特定实施例。
为了了防止显示屏幕的破裂，尤其是柔性可折叠屏幕的破裂，一般需要在屏幕上添加一覆盖板，从而对屏幕起到很好的保护作用。但是，在实际应用时，尤其在一些柔性折叠屏幕上，覆盖板的硬度和其弯折恢复性能不能相互平衡，存在着硬度过高或者不足，弯折性能过低等问题。
本揭示实施例中，提供一种聚合物薄膜。起保护作用的覆盖板主要由硬化层和柔性基底两部分组成，本揭示提供的聚合物薄膜涂布在硬化层上，进而起到调节整个覆盖板的表面硬度和弯折性能。如图1所示，图1为本揭示实施例的聚合物薄膜结构示意图。聚合物薄膜包括衬底100以及强化层101。强化层101设置在衬底100上，其中，强化层101还包括聚合物，强化层101由所述聚合物构成。
具体的，所述聚合物为A，其结构式为：
Figure PCTCN2019115440-appb-000004
具体的，所述聚合物为B，其结构式为：
Figure PCTCN2019115440-appb-000005
所述聚合物的分子结构式的侧链上包括多个刚性链段和多个柔性链段，刚性链段和柔性链段作用在聚合物的侧链上，并对聚合物的侧链进行修饰，从而达到强化的目的。本揭示实施例提供的聚合物通过在侧链上引入不同的刚性链段和柔性链段，并调节两者的比例，来对膜层进行强化，从而满足柔性可折叠显示屏的需求。
本揭示实施例提供一种聚合物薄膜的制备方法，如图2所示，图2为本揭示实施例的聚合物薄膜的制备工艺流程图。制备工艺流程包括如下步骤：
S100：将双(3-溴-4-异氰酸根合苯基)甲烷与添加物混合反应，并制备聚合物单体
在步骤S100中，主要制备聚合物的单体，为后续聚合物的制备做准备。
S101：将所述聚合物单体与乙二酸反应，制备聚合物
通过步骤S100中得到的聚合物单体，并进行一系列的化学合成反应，最终制备得到本揭示实施例的聚合物。
S102：将所述聚合物涂布在衬底上，形成聚合物薄膜
最后，将制备的聚合物涂布在衬底上，并干燥成膜，形成覆盖板上的强化膜。
具体的，在制备聚合物的过程中，聚合物的单体包括：N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)或N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)。
当所述聚合物为A，此时，聚合物A的单体化学式为C 47H 48N 4O 2，即N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)。
聚合物A由聚合物A的单体经过一系列的反应合成。具体的，首先合成聚合物A的单体，其合成过程如下：
将双(3-溴-4-异氰酸根合苯基)甲烷(4.08g,10mmol)和4-己基萘胺(4.54g,20mmol)两者物质加入到100ml的两口烧瓶中；
再加入添加物，所述添加物为碳酸铯(4.62g,24mmol)、碘化亚铜(228mg,1.2mmol)以及18-冠-6(104mg,0.4mmol)；
添加完成后，抽通三次，并向烧瓶中充入保护气体氩气，同时加入50mL除氧的N,N-二甲基丙烯基脲(DMPU)，接着，将混合物置于180℃反应24小时；
最后，将烧瓶内的物质冷却至室温，混合物倒入100ml的冰水中，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，其中分离液为二氯甲烷和正己烷，两者的体积比为1:1，得到白色固体4.2g，在整个制备工艺中，其白色固体的产率为60％，产率高于现有生产工艺中的产率。
具体的，其单体合成化学反应如下所示：
Figure PCTCN2019115440-appb-000006
对上述白色固体物质进行核磁检测，与聚合物A的单体的化学式吻合。
聚合物A的单体制备完成后，通过A的单体制备聚合物。具体的包括如下步骤：
首先，将聚合物A的单体，即N，N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)(4.2g,6mmol)和乙二酸(0.558g,6.2mmol)加入25ml圆底烧瓶中；
然后，通入氩气并排除氧气，并加入10ml稀盐酸，混合物于80℃反应12小时后停止；
最后，用50ml甲醇沉降，得到白色固体，并将白色固体依次在正己烷、丙酮中抽提两天，最终得到无色固体2.51g。
通过测定，在聚合物的合成工艺中，其产率为53％。聚合物的重均分子量为2356kg/mol，数均分子量为1980kg/mol，分散度为1.83。
具体的，其单体合成聚合物的化学反应如下所示：
Figure PCTCN2019115440-appb-000007
优选的，所述聚合物为B时，在合成过程中，聚合物B由聚合物B的单体通过一系列的化学合成制备而来，具体的，聚合物B的单体的化学式为C 59H 60N 4O 2，即N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)。
聚合物B由聚合物B的单体经过一系列的反应合成。具体的，首先合成聚合物B的单体，其合成过程如下：
首先，将双(3-溴-4-异氰酸根合苯基)甲烷(4.08g,10mmol)和10-氨基-9-辛基蒽(6.1g,20mmol)一同加入100ml两口烧瓶中；
再加入添加物，所述添加物为碳酸铯(4.62g,24mmol)、碘化亚铜(228mg,1.2mmol)以及18-冠-6(104mg,0.4mmol)；
随后，抽通三次，并充入氩气，加入50mL除氧的N,N-二甲基丙烯基脲(DMPU)，置于180℃反应24小时；
最后，将反应冷却至室温，倒入100ml冰水中，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离(二氯甲烷：正己烷v/v＝1:2)，得到白色固体4.1g，产率为48％。
具体的，其合成单体的化学反应如下：
Figure PCTCN2019115440-appb-000008
对上述白色固体物质进行核磁检测，与聚合物B的单体的化学式吻合。
聚合物B的单体制备完成后，通过B的单体制备聚合物。具体的包括如下步骤：
首先，将N，N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)(4.1g,4.7mmol)和乙二酸(0.441g,4.9mmol)加入到25ml圆底烧瓶中；
随后，通入氩气除去氧气，并加入10ml稀盐酸，80℃反应12小时后停止；
最后，用50ml甲醇沉降，得到白色固体，将白色固体依次在正己烷、丙酮中抽提两天，得到无色固体。
其中，得到的白色固体的质量为3.07g，产率为68％。聚合物B的重均分子量为2578kg/mol，数均分子量为2043kg/mol，分散度为1.79。
具体的，由单体合成聚合物B的反应如下所示：
Figure PCTCN2019115440-appb-000009
最终，制备得到本揭示实施例提供的聚合物薄膜。将其涂布在覆盖板上，当聚合物A作为硬化层时，涂布在透明聚酰亚胺上得到覆盖板的表面硬度为2H；当聚合物B作为硬化层时，涂布在透明聚酰亚胺上得到覆盖板的表面硬度为3H。硬化层的硬度均得到提升，并且，还具有好的弯折性能和抗摩擦性能。
本揭示实施例还提供一种柔性折叠面板，如图3所示，图3为本揭示实施例提供的柔性折叠面板。柔性折叠面板300上设置有本揭示实施例提供的聚合物薄膜301，聚合物薄膜301通过本揭示实施例中的制备方法制备而来。
以上对本揭示实施例所提供的一种聚合物薄膜及其制备方法、柔性折叠面板进行了详细介绍，以上实施例的说明只是用于帮助理解本揭示的技术方案及其核心思想；本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，而这些修改或者替换，并不使相应技术方案的本质脱离本揭示各实施例的技术方案的范围。

Claims (18)

  1. 一种聚合物薄膜的制备方法，包括如下步骤：
    S100：将双(3-溴-4-异氰酸根合苯基)甲烷与添加物混合反应，并制备聚合物单体；
    S101：将所述聚合物单体与乙二酸反应，制备聚合物；
    S102：将所述聚合物涂布在衬底上，形成聚合物薄膜。
    所述聚合物单体包括：N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)或N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)；
    所述聚合物的化学结构式为：
    Figure PCTCN2019115440-appb-100001
  2. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述添加物包括4-己基萘胺。
  3. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述步骤S100中，还包括如下步骤：
    S200：将双(3-溴-4-异氰酸根合苯基)甲烷和4-己基萘胺加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
    S201：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲，以形成混合物，将所述混合物置于180℃反应24小时；
    S202：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
  4. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述步骤S201中还包括如下步骤：
    S300：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)和乙二酸混合加入烧瓶中，于80℃反应12小时；
    S301：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
  5. 根据权利要求4所述的聚合物薄膜的制备方法，其中所述步骤S300中包括：在所述烧瓶中通入氩气，并加入稀盐酸。
  6. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述添加物包括10-氨基-9-辛基蒽。
  7. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述步骤S100中还包括如下步骤：
    S400：将双(3-溴-4-异氰酸根合苯基)甲烷和10-氨基-9-辛基蒽加入烧瓶中；
    S401：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,混合物置于180℃反应24小时；
    S402：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次， 将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
  8. 根据权利要求7所述的聚合物薄膜的制备方法，其中所述步骤S400中，还包括：在所述烧瓶中加入碳酸铯、碘化亚铜以及18-冠-6。
  9. 根据权利要求1所述的聚合物薄膜的制备方法，其中所述步骤S201中还包括如下步骤：
    S500：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
    S501：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
  10. 一种聚合物薄膜，包括：
    衬底；以及
    强化层；
    其中，所述强化层设置在所述衬底上，所述强化层包括聚合物，所述聚合物的侧链包括多个刚性链段和多个柔性链段，所述刚性链段和所述柔性链段对所述聚合物的所述侧链进行修饰强化。
  11. 根据权利要求10所述的聚合物薄膜，其中所述聚合物的化学结构式为：
    Figure PCTCN2019115440-appb-100002
  12. 根据权利要求10所述的聚合物薄膜，其中所述聚合物的化学结构式为：
    Figure PCTCN2019115440-appb-100003
  13. 一种聚合物薄膜的制备方法，包括如下步骤：
    S100：将双(3-溴-4-异氰酸根合苯基)甲烷与添加物混合反应，并制备聚合物单体；
    S101：将所述聚合物单体与乙二酸反应，制备聚合物；
    S102：将所述聚合物涂布在衬底上，形成聚合物薄膜。
  14. 根据权利要求13所述的聚合物薄膜的制备方法，其特征在于，所述聚合物单体包括：N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯 基))双(4-己基萘-1-胺)或N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)。
  15. 根据权利要求13所述的聚合物薄膜的制备方法，其中所述添加物包括4-己基萘胺，所述步骤S100中，还包括如下步骤：
    S200：将双(3-溴-4-异氰酸根合苯基)甲烷和4-己基萘胺加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
    S201：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,以形成混合物，将所述混合物置于180℃反应24小时；
    S202：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
  16. 根据权利要求13所述的聚合物薄膜的制备方法，其中所述步骤S201中还包括如下步骤：
    S300：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(4-己基萘-1-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
    S301：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
  17. 根据权利要求13所述的聚合物薄膜的制备方法，其中所述添加物包括10-氨基-9-辛基蒽，所述步骤S100中还包括如下步骤：
    S400：将双(3-溴-4-异氰酸根合苯基)甲烷和10-氨基-9-辛基蒽加入烧瓶中，并加入碳酸铯、碘化亚铜以及18-冠-6；
    S401：在所述烧瓶中，通入氩气，并加入除氧的N,N-二甲基丙烯基脲,混合物置于180℃反应24小时；
    S402：将所述烧瓶冷却至室温，倒入冰水，用二氯甲烷萃取三次，将有机相合并，加入硅胶，除去溶剂，柱层析进行分离，得到所述聚合物单体。
  18. 根据权利要求13所述的聚合物薄膜的制备方法，其中所述步骤S201中还包括如下步骤：
    S500：将N,N'-(亚甲基双(6-异氰酸根合-3,1-亚苯基))双(10-辛基蒽-9-胺)和乙二酸混合加入烧瓶中，通入氩气并加入稀盐酸，于80℃反应12小时；
    S501：用甲醇沉降，得到白色固体并依次在正己烷、丙酮中抽提两天，得到所述聚合物。
PCT/CN2019/115440 2019-08-19 2019-11-04 聚合物薄膜及其制备方法、柔性折叠面板 WO2021031359A1 (zh)

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