CN111785845A - Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device - Google Patents
Thin film packaging material, manufacturing method thereof, thin film packaging structure and electronic device Download PDFInfo
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- CN111785845A CN111785845A CN201910270778.7A CN201910270778A CN111785845A CN 111785845 A CN111785845 A CN 111785845A CN 201910270778 A CN201910270778 A CN 201910270778A CN 111785845 A CN111785845 A CN 111785845A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
In the film packaging material, the manufacturing method thereof, the film packaging structure and the electronic device, the cage-type polysilsesquioxane and the derivative unit thereof are introduced into the main chain or the side group of the acrylate monomer, the structural characteristics of POSS are utilized to improve the thermal stability and the light transmittance of the organic layer, and meanwhile, the tolerance of the organic layer to plasma is increased, so that the film packaging effect is improved.
Description
Technical Field
The present disclosure relates to the field of display technologies, and in particular, to a thin film encapsulation material, a method for manufacturing the thin film encapsulation material, a thin film encapsulation structure, and an electronic device.
Background
The organic electroluminescent device (OLED) is called a display device with the greatest application prospect because it has the characteristics of self-luminescence, high brightness, high contrast, low operating voltage, flexible display and the like. In recent years, with the development of curved panels and foldable display devices, various flexible OLED display devices having bendability have been developed.
A flexible OLED display device generally includes a substrate, an electroluminescent element on the substrate, and a thin film encapsulation structure on the electroluminescent element. For a flexible OLED device, the encapsulation effect of the thin film encapsulation structure directly affects the reliability and the service life of the flexible OLED device, and therefore, how to efficiently encapsulate the flexible OLED device to prolong the service life of the device is an important issue facing those skilled in the art.
The existing film packaging structure is generally formed by overlapping an inorganic packaging layer and an organic packaging layer, wherein the inorganic packaging layer can block external water vapor and oxygen, and the organic packaging layer can ensure the planarization of the surface of a packaging film and release stress. Meanwhile, the organic packaging layer has the function of coating particles, and defects in the inorganic layer are prevented from diffusing.
Currently, the organic layer is generally formed of an acrylic material or an epoxy material. However, these polymeric materials generally exhibit the characteristic of poor thermal stability. Meanwhile, since the inorganic layer is deposited by plasma, the plasma etches the organic layer during the deposition process, which destroys the encapsulation performance of the organic layer, and further causes the degradation of the OLED device.
Therefore, how to solve the problems of poor thermal stability and easy damage of the existing film packaging material becomes a technical problem to be solved urgently by the technical personnel in the field.
Disclosure of Invention
In view of the above, the present application provides a film packaging material to solve the problems of poor thermal stability and easy damage of the existing film packaging material.
In order to solve the above technical problem, the present invention provides a film packaging material, including: a photoinitiator and a compound synthesized from a cage polysilsesquioxane group and an acrylate functional group;
the structural formula of the compound is:
D1-L1-POSS or D1-L1- (POSS) n-L2-D2;
wherein POSS is a cage polysilsesquioxane group, D1 and D2 are acrylate functional groups, L1 and L2 are alkylene or alkylene ether groups, and n is an integer from 1 to 30.
Optionally, in the film encapsulating material, the structural formula of the cage-type polysilsesquioxane monomer is:
wherein R is H, alkyl, alkylene, aryl, arylene or a substituent of these groups.
Optionally, in the film encapsulating material, the structural formula of the acrylate functional group is:
wherein x represents a position bonded to L1 or L2, and Y is hydrogen or an alkyl group.
Optionally, in the film encapsulating material, the photoinitiator includes any one of acetophenone, benzophenone, benzoin, and phosphorus initiators, or any combination thereof.
The invention also provides a manufacturing method of the film packaging material, which comprises the following steps:
providing methacryloyl chloride and a POSS intermediate having a hydroxyl group;
synthesizing the methacryloyl chloride and the POSS intermediate into a compound by esterification of an acyl chloride and a hydroxyl group, the compound being synthesized from a cage polysilsesquioxane group and an acrylate functional group; and
a photoinitiator is provided and the compound is mixed with the photoinitiator.
Optionally, in the method for manufacturing a thin film encapsulation material, the step of synthesizing the methacryloyl chloride and the POSS intermediate into a compound through an esterification reaction of an acyl chloride and a hydroxyl group includes:
placing triethylamine and the POSS intermediate with hydroxyl in the same reaction container;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
Optionally, in the manufacturing method of the thin film encapsulation material, a manufacturing process of the POSS intermediate having a hydroxyl group includes:
POSS-ethylene and mercaptoethanol are placed in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a mixed solution;
irradiating the mixed solution by using an ultraviolet lamp;
carrying out suction filtration and concentration to obtain a crude product of a target intermediate; and
and purifying the crude product by a 200-300-mesh silica gel column.
Optionally, in the manufacturing method of the thin film encapsulation material, a manufacturing process of the POSS intermediate having a hydroxyl group includes:
POSS-OH and hydroxyphenylphosphoric acid are placed in the same reaction container;
heating the reaction vessel;
carrying out suction filtration and concentration to obtain a crude product of a target intermediate; and
and purifying the crude product by a 200-300-mesh silica gel column.
The present invention also provides a thin film encapsulation structure, including: laminating alternating inorganic and organic layers;
wherein, the organic layer adopts the thin film packaging material.
The present invention also provides an electronic device comprising: a substrate, a functional device and a thin film encapsulation structure as described above;
the functional device and the film packaging structure are sequentially formed on the substrate, and the film packaging structure is used for packaging the functional device.
According to the film packaging material, the manufacturing method thereof, the film packaging structure and the electronic device, the cage type polysilsesquioxane and the derivative unit thereof are introduced into the main chain or the side group of the acrylate monomer, the thermal stability and the light transmittance of the organic layer are improved by utilizing the structural characteristics of POSS, the tolerance of the organic layer to plasma is increased, and the film packaging effect is further improved.
Drawings
The technical solutions of the present invention will be described in detail below with reference to the accompanying drawings and specific embodiments so that the features and advantages of the present invention will be more apparent.
FIG. 1 is a schematic structural diagram of a thin film package structure according to an embodiment of the present invention;
fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present invention.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The same reference numerals in the drawings denote the same or similar structures, and thus their repetitive description will be omitted.
The present invention provides a novel thin film encapsulation material, comprising: a photoinitiator and a compound synthesized from a cage polysilsesquioxane group and an acrylate functional group; the structural formula of the compound is: D1-L1-POSS or D1-L1- (POSS) n-L2-D2; wherein POSS is a cage polysilsesquioxane group, D1 and D2 are acrylate functional groups, L1 and L2 are alkylene or alkylene ether groups, and n is an integer from 1 to 30.
Specifically, the polyhedral oligomeric silsesquioxane (POSS for short) refers to a polysilsesquioxane having a cage structure, which is also called polyhedral oligomeric silsesquioxane. The structural formula of the POSS monomer is as follows:
wherein R is H, alkyl, alkylene, aryl, heteroaryl or substituent of the groups, and the alkyl comprises a straight chain, a branched chain and a cyclic chain. The aryl group has 6 to 30 carbon atoms, the heteroaryl group has 3 to 30 carbon atoms, and the alkyl group has 1 to 20 carbon atoms.
The structure of the POSS monomer can be divided into an inorganic framework formed by Si-O bonds and an organic part formed by external organic groups. The POSS takes a polyhedral inorganic framework as a core, so that the POSS can ensure good heat resistance. The substituent R on the Si atom at the vertex of the polyhedron may be any of various reactive or non-reactive groups, and reactivity or functionality may be imparted to the POSS by changing the type of organic group attached to the Si end.
The acrylate is a generic term for esters of acrylic acid and its homologues, including methyl acrylate, ethyl acrylate, 2-methyl methacrylate, 2-ethyl methacrylate, and the like. The structural formula of the acrylate functional group is as follows:
wherein x represents a position bonded to L1 or L2, and Y is hydrogen or an alkyl group. In this embodiment, the alkyl group has 1 to 10 carbon atoms. L1 and L2 are alkylene or alkylene ether groups. In this embodiment, the alkylene group has 1 to 30 carbon atoms, and the alkylene ether group has 1 to 50 carbon atoms.
In compounds synthesized from a cage polysilsesquioxane group and an acrylate functional group, the cage polysilsesquioxane group is linked to the acrylate functional group (D1 or D2) through L1 or L2. Wherein, L1 and L2 may be the same or different. D1 and D2 may be the same or different.
The compound is mixed with a photoinitiator, wherein the photoinitiator comprises any one or any combination of acetophenone, benzophenone, benzoin and phosphorus initiators and is used for causing photocuring reaction.
In the film packaging material, the compound contains the cage polysilsesquioxane group, the refractive index of the group structure is large, the extinction coefficient is small, light transmission is facilitated, and Si-O bonds in the cage polysilsesquioxane group have higher bond energy compared with C-C bonds of existing organic materials, so that the compound has good light transmittance and thermal stability and can resist bombardment of plasma. Therefore, the film packaging material is adopted as the organic layer for film packaging, so that the thermal stability and light transmittance of the organic layer can be improved, and the tolerance of the organic layer to plasma can be increased.
Correspondingly, the invention also provides a manufacturing method of the film packaging material, which comprises the following steps:
the method comprises the following steps: providing methacryloyl chloride and a POSS intermediate having a hydroxyl (-OH) group;
step two: synthesizing the methacryloyl chloride and the POSS intermediate into a compound by esterification of an acyl chloride and a hydroxyl group, the compound being synthesized from a cage polysilsesquioxane group and an acrylate functional group;
step three: a photoinitiator is provided and the compound is mixed with the photoinitiator.
In particular, methacryloyl chloride is an intermediate product, and can be directly purchased from the market. The structural formula of methacryloyl chloride is:
in this example, a POSS intermediate having a hydroxyl group was prepared using mercaptoethanol and POSS-ethylene as raw materials. The specific reaction equation is as follows:
the preparation process of the POSS intermediate with the hydroxyl comprises the following steps: firstly, POSS-ethylene (0.57g, 1mmol) and mercaptoethanol (0.08g, 1mmol) are placed in the same reaction vessel; next, dichloromethane (10mL) was added to the reaction vessel to form a mixed solution; then, the mixed solution was placed under an ultraviolet lamp with λ 365nm for 60 minutes; then, obtaining a crude product of the target intermediate through suction filtration and concentration; and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target intermediate.
In another embodiment of the invention, the POSS intermediate having hydroxyl groups is prepared from hydroxyphenylphosphoric acid and POSS-OH as starting materials. The specific reaction equation is as follows:
the preparation process of the POSS intermediate with the hydroxyl comprises the following steps: firstly, POSS-OH (0.57g, 1mmol)) and hydroxyphenylphosphoric acid (0.18g, 1mmol) are placed in the same reaction vessel; then, heating the reaction vessel at 100 ℃ for 60 minutes; then, obtaining a crude product of the target intermediate through suction filtration and concentration; and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target intermediate.
It should be noted that the above-mentioned POSS intermediate having a hydroxyl group and the preparation method thereof are merely examples and not limitations, and in other embodiments of the present invention, the POSS intermediate having a hydroxyl group can be prepared by using other raw materials and other methods.
After a POSS intermediate having a hydroxyl group is obtained, methacryloyl chloride and the POSS intermediate are synthesized into a compound by an esterification reaction of an acid chloride and a hydroxyl group. In this example, the reaction equation for synthesizing methacryloyl chloride and POSS intermediates into a compound by esterification of acyl chloride and hydroxyl groups is:
specifically, the process for synthesizing the methacryloyl chloride and the POSS intermediate into the compound through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
first, triethylamine (0.15g, 1.5mmol) and the POSS intermediate having a hydroxyl group (0.60g, 1mmol) were placed in the same reaction vessel;
next, dichloromethane (10mL) was added to the reaction vessel to form a first mixed solution;
thereafter, methacryloyl chloride (0.15g, 1.5mmol) was dissolved in dichloromethane to form a second mixed solution;
then, the second mixed solution was added dropwise to the first mixed solution to carry out a reaction, ice bath control was carried out for 30 minutes at the beginning of the reaction, and then a room-temperature reaction was carried out for 24 hours;
then, obtaining a crude product of the target compound through suction filtration and concentration;
and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target compound, wherein the target compound introduces a sulfur group and a POSS group into a main chain or a side group of the acrylate monomer.
In another embodiment of the present invention, the reaction equation for the synthesis of methacryloyl chloride and POSS intermediates into a compound by esterification of the acid chloride and hydroxyl groups is:
specifically, the process for synthesizing the methacryloyl chloride and the POSS intermediate into the compound through the esterification reaction of the acyl chloride and the hydroxyl comprises the following steps:
firstly, triethylamine (0.30g, 3mmol) and the POSS intermediate having a hydroxyl group (0.71g, 1mmol) are placed in the same reaction vessel;
next, dichloromethane (10mL) was added to the reaction vessel to form a first mixed solution;
thereafter, methacryloyl chloride (0.30g, 3mmol) was dissolved in dichloromethane to form a second mixed solution;
then, the second mixed solution was added dropwise to the first mixed solution to carry out a reaction, ice bath control was carried out for 30 minutes at the beginning of the reaction, and then a room-temperature reaction was carried out for 24 hours;
then, obtaining a crude product of the target compound through suction filtration and concentration;
and finally, purifying the crude product through a 200-300-mesh silica gel column to obtain a target compound, wherein phosphate groups and POSS groups are introduced into a main chain or a side group of the acrylate monomer by the target compound.
It should be noted that the above compounds and their preparation methods are merely exemplary and not limiting, and in other embodiments of the present invention, different POSS intermediates and processes may be used, as long as the compounds synthesized from cage polysilsesquioxane groups and acrylate functional groups can be formed by esterification of acid chlorides and hydroxyl groups.
After the target compound is formed, the target compound is mixed with a photoinitiator, whereby the thin film encapsulation material is obtained. The film packaging material not only has better thermal stability and light transmittance, but also can resist the bombardment of plasma, and avoids the performance deterioration of an OLED device caused by the damage of the packaging performance due to the etching of the plasma.
Correspondingly, the invention also provides a film packaging structure. Fig. 1 is a schematic structural diagram of a thin film package structure according to an embodiment of the invention. As shown in fig. 1, the thin film encapsulation structure 30 includes: alternating inorganic layers 31 and organic layers 32 are stacked, and the organic layers 32 employ a thin film encapsulation material as described above.
Correspondingly, the invention also provides an electronic device. Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the invention. As shown in fig. 2, the electronic device 1 includes a substrate 10, a functional device 20, and a thin film encapsulation structure 30 as described above; the functional device 20 and the thin film encapsulation structure 30 are sequentially formed on the substrate 10, and the thin film encapsulation structure 30 is used for encapsulating the functional device 20.
Specifically, the substrate 10 may be a rigid substrate, or may be a flexible substrate, preferably a flexible substrate, so as to implement a flexible display function. The rigid substrate may be, for example, a glass substrate or a quartz substrate. The flexible substrate may be an organic polymer substrate such as a polyimide substrate (PI substrate), a polyamide substrate, a polycarbonate substrate, or a polyether sulfone substrate.
The functional device 20 includes, but is not limited to, an electroluminescent element (e.g., OLED), a liquid crystal display device, a solar cell, a thin film battery, an organic sensor, and other electronic devices.
The thin film encapsulation structure 30 includes organic layers and inorganic layers alternately stacked, and the thin film positioned at the lowermost layer and/or the uppermost layer may be either an organic layer or an inorganic layer. Wherein the organic layer is made of the above thin film encapsulation material comprising a compound synthesized from a cage-type polysilsesquioxane group and an acrylate functional group, and thus the organic layer has good thermal stability and light transmittance while having stronger resistance to plasma. Therefore, in the process of forming the inorganic layer by the plasma deposition process, the organic layer can also be prevented or reduced from being damaged, so that the packaging effect of the thin film packaging structure 30 is ensured, and the problem of performance degradation of an electronic device is avoided.
In summary, according to the film packaging material, the manufacturing method thereof, the film packaging structure and the electronic device provided by the invention, the cage-type polysilsesquioxane and the derivative unit thereof are introduced into the main chain or the side group of the acrylate monomer, the structural characteristics of POSS are utilized to improve the thermal stability and the light transmittance of the organic layer, and meanwhile, the tolerance of the organic layer to plasma is increased, so that the film packaging effect is improved.
The foregoing is a more detailed description of the present application in connection with specific preferred embodiments and it is not intended that the present application be limited to these specific details. For those skilled in the art to which the present application pertains, several simple deductions or substitutions may be made without departing from the concept of the present application, and all should be considered as belonging to the protection scope of the present application.
Claims (10)
1. A thin film encapsulation material, comprising: a photoinitiator and a compound synthesized from a cage polysilsesquioxane group and an acrylate functional group;
the structural formula of the compound is:
D1-L1-POSS or D1-L1- (POSS) n-L2-D2;
wherein POSS is a cage polysilsesquioxane group, D1 and D2 are acrylate functional groups, L1 and L2 are alkylene or alkylene ether groups, and n is an integer from 1 to 30.
2. The film encapsulating material of claim 1, wherein the cage polysilsesquioxane monomer has the formula:
wherein R is H, alkyl, alkylene, aryl, arylene or a substituent of these groups.
3. The film encapsulating material of claim 1, wherein the acrylate functional group has the formula:
wherein x represents a position bonded to L1 or L2, and Y is hydrogen or an alkyl group.
4. The film encapsulation material according to claim 1, wherein the photoinitiator comprises any one or any combination of acetophenone, benzophenone, benzoin, and phosphorus initiators.
5. A method of manufacturing a thin film encapsulation material, comprising:
providing methacryloyl chloride and a POSS intermediate having a hydroxyl group;
synthesizing the methacryloyl chloride and the POSS intermediate into a compound by esterification of an acyl chloride and a hydroxyl group, the compound being synthesized from a cage polysilsesquioxane group and an acrylate functional group; and
a photoinitiator is provided and the compound is mixed with the photoinitiator.
6. The method of manufacturing a thin film encapsulation material according to claim 5, wherein the synthesizing of the methacryloyl chloride and the POSS intermediate into the compound through the esterification reaction of the acyl chloride and the hydroxyl group comprises:
placing triethylamine and the POSS intermediate with hydroxyl in the same reaction container;
adding dichloromethane to the reaction vessel to form a first mixed solution;
dissolving the methacryloyl chloride in methylene chloride to form a second mixed solution;
dropwise adding the second mixed solution into the first mixed solution to perform reaction;
carrying out suction filtration and concentration to obtain a crude product of the target compound; and
and purifying the crude product by a 200-300-mesh silica gel column.
7. The method of manufacturing a thin film encapsulation material according to claim 6, wherein the process of manufacturing the POSS intermediate having hydroxyl group comprises:
POSS-ethylene and mercaptoethanol are placed in the same reaction vessel;
adding dichloromethane to the reaction vessel to form a mixed solution;
irradiating the mixed solution by using an ultraviolet lamp;
carrying out suction filtration and concentration to obtain a crude product of a target intermediate; and
and purifying the crude product by a 200-300-mesh silica gel column.
8. The method of manufacturing a thin film encapsulation material according to claim 6, wherein the process of manufacturing the POSS intermediate having hydroxyl group comprises:
POSS-OH and hydroxyphenylphosphoric acid are placed in the same reaction container;
heating the reaction vessel;
carrying out suction filtration and concentration to obtain a crude product of a target intermediate; and
and purifying the crude product by a 200-300-mesh silica gel column.
9. A thin film encapsulation structure, comprising: laminating alternating inorganic and organic layers; wherein the organic layer adopts the thin film packaging material as claimed in any one of claims 1 to 4.
10. An electronic device, comprising: a substrate, a functional device and a thin film encapsulation structure according to claim 9;
the functional device and the film packaging structure are sequentially formed on the substrate, and the film packaging structure is used for packaging the functional device.
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| WO2023065723A1 (en) | 2021-10-19 | 2023-04-27 | 杭州福斯特电子材料有限公司 | Ink composition for oled packaging and application thereof |
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