WO2022027769A1 - 偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法 - Google Patents

偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法 Download PDF

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WO2022027769A1
WO2022027769A1 PCT/CN2020/113756 CN2020113756W WO2022027769A1 WO 2022027769 A1 WO2022027769 A1 WO 2022027769A1 CN 2020113756 W CN2020113756 W CN 2020113756W WO 2022027769 A1 WO2022027769 A1 WO 2022027769A1
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light
azophenyl
azobenzene
azobenzene derivative
reversible adhesive
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PCT/CN2020/113756
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English (en)
French (fr)
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吴豪旭
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深圳市华星光电半导体显示技术有限公司
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Priority to US16/980,447 priority Critical patent/US20220041544A1/en
Publication of WO2022027769A1 publication Critical patent/WO2022027769A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/80—Manufacture or treatment specially adapted for the organic devices covered by this subclass using temporary substrates
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K77/00—Constructional details of devices covered by this subclass and not covered by groups H10K10/80, H10K30/80, H10K50/80 or H10K59/80
    • H10K77/10—Substrates, e.g. flexible substrates
    • H10K77/111—Flexible substrates
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the invention belongs to the technical field of adhesive materials, and in particular relates to an azobenzene derivative and a preparation method thereof, as well as an azophenyl light-controlled reversible adhesive and a use method thereof.
  • Flexible displays have the characteristics of lightness, thinness, rollability, and impact resistance, and have a huge potential market in the field of portable electronic products.
  • Displays such as Liquid Crystal Display (LCD) and Organic Light Emitting Display (OLCD) can all realize flexible display.
  • LCD Liquid Crystal Display
  • OLED Organic Light Emitting Display
  • the laser lift-off technology is to set the flexible substrate on the glass substrate (that is, use the glass substrate as the carrier substrate), and then prepare the display device on the flexible substrate. After the preparation, the contact interface between the glass substrate and the flexible substrate is irradiated with laser light. The flexible substrate is separated from the glass substrate.
  • the energy When the laser irradiates the contact interface between the glass substrate and the flexible substrate, the energy will also be absorbed by the flexible substrate, causing the flexible substrate to ablate and release gas, so the flexible substrate will expand locally, form wrinkles after cooling, and even local stress is too large , warping occurs, resulting in defective products.
  • the present invention provides an azobenzene derivative and a preparation method thereof, as well as an azophenyl light-controlled reversible adhesive and a use method thereof.
  • the technical scheme provided by the present invention is:
  • a kind of azobenzene derivative, its molecular structure is as follows:
  • An azophenyl light-controlled reversible adhesive comprising the above-mentioned P1 and/or P2.
  • a method of using the above-mentioned azophenyl light-controlled reversible adhesive comprising the following steps:
  • the invention utilizes alkyl chain and bis-naphthol to jointly adjust azobenzene derivatives P1 and P2 to a melting point slightly higher than room temperature, liquid P1 and P2 can be cured spontaneously and rapidly within 2 minutes, and show excellent adhesion after curing performance, its bonding strength can reach several MPa to meet the needs of subsequent processes; under green light irradiation, the photothermal effect of P1 and P2 leads to the transformation of solid to liquid, after green light irradiation (under the same power and light time conditions, Only green light (500 ⁇ 550nm, 175mW cm-2, 480s ⁇ 500s) can realize the transition of P1 and P2 from solid state to liquid state.), P1 and P2 heat up to melt and lose their adhesive properties, and this process is highly reversible.
  • the heat can be isolated from the outer glass side by the porous structure composed of the added ceramic fiber particles, and the middle layer will peel off while the heat cannot penetrate to the side of the panel.
  • the adhesive of the optical switch (azophenyl light-controlled reversible adhesive) is extremely soluble in common organic solvents such as dichloromethane, easy to be cleaned and recovered, and can be recycled.
  • the method is easy to operate, low in cost, and can eliminate the problem of product defects caused by laser peeling, and can be used as a potential flexible substrate peeling technology.
  • Fig. 1 is P1 of the present invention along with the heating of green light irradiation time and the picture of solid-liquid transition;
  • Fig. 2 is P1 and P2 solid absorption spectrum of the present invention
  • Figure 3 is a schematic diagram of the action of the azophenyl light-controlled reversible adhesive of the present invention.
  • the invention utilizes alkyl chain and bis-naphthol to jointly adjust azobenzene derivatives P1 and P2 to a melting point slightly higher than room temperature, liquid P1 and P2 can be cured spontaneously and rapidly within 2 minutes, and show excellent adhesion after curing performance, its bonding strength can reach several MPa to meet the needs of subsequent processes; under green light irradiation, the photothermal effect of P1 and P2 leads to the transformation of solid to liquid, after green light irradiation (under the same power and light time conditions, Only green light (500 ⁇ 550nm, 175mW cm-2, 480s ⁇ 500s) can realize the transition from solid to liquid state of P1 and P2.), P1 and P2 are heated and melted and lose their adhesive properties, and this process is highly reversible.
  • the heat can be isolated from the outer glass side by the porous structure composed of the added ceramic fiber particles, and the heat cannot penetrate to the side of the panel, and at the same time, the middle layer peels off.
  • the adhesive of this optical switch (azophenyl light-controlled reversible adhesive) is extremely soluble in common organic solvents such as dichloromethane, easy to clean and recover, and can be recycled.
  • the method is easy to operate, low in cost, and can eliminate the problem of product defects caused by laser peeling, and can be used as a potential flexible substrate peeling technology.
  • An azobenzene derivative denoted as P1
  • P1 has the following molecular structure:
  • the preparation method of P1 is as follows: taking azobenzene, 3,4,5-tripentyloxybenzoic acid and 2,2'-dihydroxy-1,1'-bisnaphthalene in the substance ratio of 1:1:1 Phenol, put the above three kinds of raw materials into the reaction kettle filled with water and participate in the reaction together, stir evenly, at 20 ° C, continue to react for 30min, the mixture after the reaction is filtered (suction filtration) and dried, and the obtained orange solid is P1 , and its melting point was measured to be 44°C.
  • the preparation method of the invention is simple and low in cost, and can react at room temperature with water as a medium without a catalyst, and the conversion rate of raw materials is as high as 85%-93%.
  • P1 is easily soluble in common organic solvents such as dichloromethane, easy to clean and recover, and can be recycled.
  • the preparation method of P1 is as follows: taking azobenzene, 3,4,5-tripentyloxybenzoic acid and 2,2'-dihydroxy-1,1 in a substance ratio of 1:0.5:1.5 '-Binaphthol, put the above-mentioned three kinds of raw materials into a reaction kettle filled with water to participate in the reaction together, stir evenly, at 25 ° C, continue to react for 20min, the mixture after the reaction is filtered (suction filtration) and dried, and the obtained orange The solid is P1.
  • the preparation method of P1 is as follows: take azobenzene, 3,4,5-tripentyloxybenzoic acid and 2,2'-dihydroxy-1,1 in a substance ratio of 1:1.5:0.5 '-Binaphthol, put the above three kinds of raw materials into a reaction kettle filled with water to participate in the reaction together, stir evenly, at 30 ° C, continue to react for 25min, the mixture after the reaction is filtered (suction filtration) and dried, and the obtained orange The solid is P1.
  • An azobenzene derivative denoted as P2 has the following molecular structure:
  • the preparation method of P2 is as follows: take azobenzene, 3,4,5-tridodecyloxybenzoic acid and 2,2'-dihydroxy-1,1'-bis- Naphthol, put the above-mentioned three kinds of raw materials into a reaction kettle filled with water and participate in the reaction together, stir evenly, at 20 ° C, continue the reaction for 20 min, filter the reacted mixture (suction filtration) and dry, and the obtained orange solid is P2.
  • the preparation method of P2 is as follows: taking azobenzene, 3,4,5-tridodecyloxybenzoic acid and 2,2'-dihydroxy-1 in a substance ratio of 1:0.5:1.5, 1'-bisnaphthol, put the above-mentioned three kinds of raw materials into the reaction kettle filled with water and participate in the reaction together, stir evenly, at 25 °C, continue to react for 30min, the mixture after the reaction is filtered (suction filtration) and dried, and the obtained The orange solid is P2.
  • the preparation method of P2 is as follows: taking azobenzene, 3,4,5-tridodecyloxybenzoic acid and 2,2'-dihydroxy-1 in a substance ratio of 1:1.5:0.5, 1'-bisnaphthol, put the above-mentioned three kinds of raw materials into a reaction kettle filled with water and participate in the reaction together, stir evenly, at 30 ° C, continue to react for 25min, the mixture after the reaction is filtered (suction filtration) and dried, and the obtained The orange solid is P2.
  • An azophenyl light-controlled reversible adhesive comprising P1 and/or P2 described in any one of Embodiments 1-6.
  • the method for using the azophenyl light-controlled reversible adhesive comprises the following steps:
  • the glass substrate is irradiated with green light, and the irradiation time of the green light is greater than or equal to 8 minutes, for example, 9 minutes of irradiation, so that the azophenyl light-controlled reversible adhesive is rapidly converted from solid to liquid;
  • the method is simple in operation, low in cost, easily soluble in common organic solvents such as dichloromethane, easy to clean and recycle, recyclable, can eliminate the problem of product defects caused by laser peeling, and can be used as a potential flexible substrate peeling technology.
  • the azobenzene derivative P1 obtained in Example 1 was placed at room temperature, and continuously irradiated with green light (500-550nm, 175mW cm-2) for 480s, and the temperature and state change of the azobenzene derivative P1 during the recording process were recorded. ,As shown in Figure 1. After being irradiated with green light for 480s, the temperature of the azobenzene derivative P1 rose to 50 °C, and changed from solid to liquid, indicating that the photothermal effect of P1 did lead to its solid-to-liquid transition under green light irradiation, and the solid The phenomenon of liquid phase change is very obvious.
  • the azobenzene derivative P1 obtained in Example 1 was coated on the opposite side of the flexible substrate and the glass substrate, so that the two were bonded together. After standing for 2 minutes, it was cured. After curing, the bonding strength reached 1.34 MPa. As shown in Figure 3.
  • the azobenzene derivative P1 After being irradiated with green light for 500 s, the azobenzene derivative P1 turned into a liquid state and basically lost its bonding effect. When the light was stopped, with the release of heat, the liquid azobenzene derivative P1 quickly and spontaneously recovered to a solid state within 2 min, and the bonding strength reached 1.32 MPa after curing.
  • the present invention utilizes the alkyl chain and bis-naphthol to jointly adjust the azobenzene derivatives P1 and P2 to a melting point slightly higher than room temperature (44° C. and 53° C. respectively), and the liquid P1 and P2 can be spontaneously and rapidly within 2 minutes. After curing, it exhibits excellent adhesive properties, and its bond strength can reach several MPa to meet the needs of subsequent processes. Under green light irradiation, the photothermal effect of P1 and P2 led to a solid-to-liquid transition. After green light irradiation, P1 and P2 heated up and melted, losing their adhesive properties. This process was highly reversible. In the process, the heat can be isolated from the outer glass side by the porous structure composed of the added ceramic fiber particles, and the heat cannot penetrate to the side of the panel, and at the same time, the middle layer peels off.

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  • Engineering & Computer Science (AREA)
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Abstract

一种偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法。偶氮苯衍生物的结构如P1和P2所示。其制备方法为使用偶氮苯基团和3,4,5-三戊氧基苯甲酸或3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚发生酯化反应，即可得到P1或P2，利用烷基链和双萘酚共同调节偶氮苯衍生物P1和P2到一个稍高于室温的熔点。

Description

偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法 技术领域
本发明属于粘合材料技术领域，具体来说，涉及一种偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法。
背景技术
柔性显示器具有轻薄、可卷曲、耐冲击等特点，在便携类电子产品领域具有巨大的潜在市场。液晶显示器(Liquid Crystal Display，简称LCD)、有机发光显示器(Organic Light Emitting Display，简称OLCD)等显示器均可以实现柔性显示。
在柔性显示器制备过程中，如何将柔性基板与载体基板分离是柔性显示技术领域中制备柔性器件的关键技术。现有技术中通常采用机械剥离或激光剥离技术，激光剥离技术对柔性基板的损伤较小，因此被广泛应用。激光剥离技术是将柔性基板设置于玻璃基板(即以玻璃基板作为载体基板)上，再在柔性基板上制备显示器件，制备完后，再用激光照射玻璃基板和柔性基板的接触界面，从而将柔性基板与玻璃基板分离。
技术问题
当激光照射玻璃基板和柔性基板的接触界面时，能量也会被柔性 基板吸收，使得柔性基板发生烧蚀并放出气体，因此柔性基板的局部会发生膨胀，冷却后形成褶皱，甚至局部应力过大，发生翘曲，造成产品不良。
技术解决方案
为解决上述技术问题，本发明提供了一种偶氮苯衍生物及其制备方法以及偶氮苯基光控可逆粘合剂及其使用方法。
为解决上述技术问题，本发明提供的技术方案为：
一种偶氮苯衍生物，其分子结构如下：
Figure PCTCN2020113756-appb-000001
一种偶氮苯基光控可逆粘合剂，包括上述的P1和/或P2。
一种上述偶氮苯基光控可逆粘合剂的使用方法，包括以下步骤：
SS1、将液体状态的所述偶氮苯基光控可逆粘合剂涂覆于柔性基板与玻璃基板相对的一面，使两者贴合，静置；
SS2、在所述柔性基板上制备显示器件；
SS3、采用绿光照射所述玻璃基板；
[根据细则91更正 24.09.2020]　
SS4、分别对所述柔性基板和玻璃基板施加相反的力，使两者分离。
有益效果
本发明利用烷基链和双萘酚共同调节偶氮苯衍生物P1和P2到一个稍高于室温的熔点，液态P1和P2可在2min内自发且快速固化，固化后表现出优良的粘合性能，其粘结强度可达几个兆帕满足后续制程需求；绿光照射下，P1和P2的光热效应导致了固体到液体的转变，绿光照射后(相同功率和光照时间的条件下，只有绿光(500～550nm，175mW cm-2，480s～500s)能够实现P1和P2从固态到液态的转变。)，P1和P2升温熔化，失去粘合性能，此过程高度可逆。而制程中热量可被加入的陶瓷纤维颗粒组成的多孔结构隔绝在外围玻璃一侧，热量无法渗透到面板一侧的同时，中间层发生剥落。这种光开关的粘合剂(偶氮苯基光控可逆粘合剂)极易溶于二氯甲烷等常见有机溶剂，容易清洗回收，可循环使用。该方法操作简易，成本较低，且可消除激光剥离带来的产品不良问题，可作为潜在的柔性基板剥离技术。
附图说明
图1为本发明的P1随着绿光照射时间的升温及固液态转变图片；
图2为本发明的P1和P2固体吸收光谱；
图3为本发明的偶氮苯基光控可逆粘合剂作用示意图。
本发明的实施方式
为了使本发明所要解决的技术问题、技术方案及有益效果更加清楚明白，以下结合附图及实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明利用烷基链和双萘酚共同调节偶氮苯衍生物P1和P2到一个稍高于室温的熔点，液态P1和P2可在2min内自发且快速固化，固化后表现出优良的粘合性能，其粘结强度可达几个兆帕满足后续制程需求；绿光照射下，P1和P2的光热效应导致了固体到液体的转变，绿光照射后(相同功率和光照时间的条件下，只有绿光(500～550nm，175mW cm-2，480s～500s)能够实现P1和P2从固态到液态的转变。)，P1和P2升温熔化，失去粘合性能，此过程高度可逆。而制程中热量可被加入的陶瓷纤维颗粒组成的多孔结构隔绝在外围玻璃一侧，热量无法渗透到面板一侧的同时，中间层发生剥落。这种光开关的粘合剂(偶氮苯基光控可逆粘合剂)极易溶于二氯甲烷等常见有机溶剂，容易清洗回收，可循环使用。该方法操作简易，成本较低，且可消除激光剥离带来的产品不良问题，可作为潜在的柔性基板剥离技术。
实施例1
一种偶氮苯衍生物，记为P1，其分子结构如下：
Figure PCTCN2020113756-appb-000002
P1的制备方法为：取物质的量比为1:1:1的偶氮苯、3,4,5-三戊氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种原料投入盛有水的反应釜中一起参与反应，搅拌均匀，在20℃下，持续反应30min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P1，测量其熔点为44℃。
本发明所述的制备方法简单，成本低廉，在室温下以水为介质、无需催化剂，即可发生反应，且原料转化率高达85％-93％。
P1作为光开关的粘合剂(偶氮苯基光控可逆粘合剂)极易溶于二氯甲烷等常见有机溶剂，容易清洗回收，可循环使用。
实施例2
本实施例中P1的制备方法为：取物质的量比为1:0.5:1.5的偶氮苯、3,4,5-三戊氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种原料投入盛有水的反应釜中一起参与反应，搅拌均匀，在25℃下，持续反应20min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P1。
实施例3
本实施例中P1的制备方法为：取物质的量比为1:1.5:0.5的偶氮苯、3,4,5-三戊氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种原 料投入盛有水的反应釜中一起参与反应，搅拌均匀，在30℃下，持续反应25min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P1。
实施例4
一种偶氮苯衍生物，记为P2，其分子结构如下：
Figure PCTCN2020113756-appb-000003
[根据细则91更正 24.09.2020]　
P2的制备方法为：取物质的量比为1:1:1的偶氮苯、3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种原料投入盛有水的反应釜中一起参与反应，搅拌均匀，在20℃下，持续反应20min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P2。
实施例5
[根据细则91更正 24.09.2020]　
本实施例中P2的制备方法为：取物质的量比为1:0.5:1.5的偶氮苯、3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种原料投入盛有水的反应釜中一起参与反应，搅拌均匀，在25℃下，持续反应30min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P2。
实施例6
[根据细则91更正 24.09.2020]　
本实施例中P2的制备方法为：取物质的量比为1:1.5:0.5的偶氮苯、3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚，将上述三种 原料投入盛有水的反应釜中一起参与反应，搅拌均匀，在30℃下，持续反应25min，反应后的混合物过滤(抽滤)烘干，得到的橙色固体即为P2。
实施例7
一种偶氮苯基光控可逆粘合剂，包括实施例1-6任意一项中所述的P1和/或P2。
所述偶氮苯基光控可逆粘合剂的使用方法，包括以下步骤：
SS1、将液体状态的所述偶氮苯基光控可逆粘合剂涂覆于柔性基板与玻璃基板相对的一面，使两者贴合，静置时间大于等于2min，例如静置3min，使偶氮苯基光控可逆粘合剂在室温下快速固化；
SS2、在所述柔性基板上制备显示器件；
SS3、采用绿光照射所述玻璃基板，绿光的照射时间大于等于8min，例如照射9min，使偶氮苯基光控可逆粘合剂快速由固体转化为液体；
[根据细则91更正 24.09.2020]　
SS4、分别对所述柔性基板和玻璃基板施加相反的力，使两者分离。
该方法操作简单，成本低廉，极易溶于二氯甲烷等常见有机溶剂，容易清洗回收，可循环使用，可消除激光剥离带来的产品不良问题，可作为潜在的柔性基板剥离技术。
试验例1
将实施例1中所得到的偶氮苯衍生物P1置于室温下，用绿光(500～550nm，175mW cm-2)持续照射480s，记录过程中偶氮苯衍生物P1的温度及状态变化，如图1所示。绿光持续照射480s后，偶 氮苯衍生物P1的温度上升到50℃，由固体变成了液体，说明在绿光照射下，P1的光热效应确实导致了其固体到液体的转变，且固液相变现象十分显著。
试验例2
取5mg实施例1中所得到的偶氮苯衍生物P1以及5mg实施例4中所得到的偶氮苯衍生物P2测定其吸收光谱，证明偶氮苯衍生物P1和偶氮苯衍生物P2在绿光区确实存在吸收，如图2所示。
试验例3
将实施例1中所得到的偶氮苯衍生物P1涂覆于柔性基板与玻璃基板相对的一面，使两者贴合，静置2min后即可固化，固化后粘结强度达到了1.34MPa，如图3所示。
采用绿光照射500s后，偶氮苯衍生物P1转变成液态，基本失去粘结效果。停止光照，随着热量的释放，液态的偶氮苯衍生物P1在2min内快速自发恢复到固态，且固化后粘结强度达到了1.32MPa。
本发明利用烷基链和双萘酚共同调节偶氮苯衍生物P1和P2到一个稍高于室温的熔点(分别为44℃和53℃)，液态P1和P2即可在2min内自发且快速固化，固化后表现出优良的粘合性能，其粘结强度可达几个兆帕满足后续制程需求。绿光照射下，P1和P2的光热效应导致了固体到液体的转变，绿光照射后，P1和P2升温熔化，失去粘合性能，此过程高度可逆。而制程中热量可被加入的陶瓷纤维颗粒组成的多孔结构隔绝在外围玻璃一侧，热量无法渗透到面板一侧的同时，中间层发生剥落。
以上内容仅为本发明的较佳实施例，对于本领域的普通技术人员，依据本发明的思想，在具体实施方式及应用范围上可以作出许多变化，只要这些变化未脱离本发明的构思，均属于本发明的保护范围。

Claims (10)

  1. 一种偶氮苯衍生物，其中，其分子结构如下：
    Figure PCTCN2020113756-appb-100001
  2. 权利要求1所述的偶氮苯衍生物的制备方法，其中，使用偶氮苯基团和3,4,5-三戊氧基苯甲酸或3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚发生酯化反应，即可得到P1或P2。
  3. 权利要求2所述的偶氮苯衍生物的制备方法，其中，将所述偶氮苯基团和3,4,5-三戊氧基苯甲酸或3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚的反应介质为水，将上述三种原料投入水中一起参与反应，即可得到P1或P2。
  4. 权利要求2所述的偶氮苯衍生物的制备方法，其中，反应时间为20min-40min。
  5. 权利要求2所述的偶氮苯衍生物的制备方法，其中，反应温 度为20℃-30℃。
  6. 权利要求2所述的偶氮苯衍生物的制备方法，其中，所述偶氮苯基团和3,4,5-三戊氧基苯甲酸或3,4,5-三十二氧基苯甲酸与2,2'-二羟基-1,1'-双萘酚的物质的量比为1:0.5-2:0.5-2。
  7. 一种偶氮苯基光控可逆粘合剂，其中，包括权利要求1中所述的P1和/或P2。
  8. [根据细则91更正 24.09.2020]
    一种偶氮苯基光控可逆粘合剂的使用方法，其中，包括以下步骤：
    SS1、将液体状态的偶氮苯基光控可逆粘合剂涂覆于柔性基板与玻璃基板相对的一面，使两者贴合，静置；
    SS2、在所述柔性基板上制备显示器件；
    SS3、采用绿光照射所述玻璃基板；
    SS4、分别对所述柔性基板和玻璃基板施加相反的力，使两者分离。
  9. 根据权利要求8所述的偶氮苯基光控可逆粘合剂的使用方法，其中，所述步骤SS1中的静置时间大于等于2min。
  10. 根据权利要求8所述的偶氮苯基光控可逆粘合剂的使用方法，其中，所述步骤SS3中的绿光的照射时间大于等于8min。
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