CN113234100B - Silicon-containing monomer, packaging composition, packaging structure and photoelectric device - Google Patents
Silicon-containing monomer, packaging composition, packaging structure and photoelectric device Download PDFInfo
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- CN113234100B CN113234100B CN202110491255.2A CN202110491255A CN113234100B CN 113234100 B CN113234100 B CN 113234100B CN 202110491255 A CN202110491255 A CN 202110491255A CN 113234100 B CN113234100 B CN 113234100B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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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
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- 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
Abstract
The invention discloses a silicon-containing monomer, a packaging composition, a packaging structure and a photoelectric device, belonging to the technical field of light-cured materials and thin film packaging, wherein the silicon-containing monomer has a structural general formula as follows:
Description
Technical Field
The invention relates to the technical field of light-cured materials and thin film packaging, in particular to a silicon-containing monomer, a packaging composition, a packaging structure and a photoelectric device.
Background
Organic Light-Emitting Diodes (OLEDs) can be fabricated on flexible, lightweight, durable plastic substrates, can achieve truly flexible display, and can be widely applied to high-performance displays.
One of the biggest problems of the current stage of OLEDs is short lifetime, which is prone to failure. One of the main factors influencing the service life of the OLED is that moisture and oxygen exist inside the OLED device after long-term use, and the existing photoelectric device has the problem of high moisture transmittance. Therefore, in order to increase the lifespan of the OLED, improving the encapsulation process of the OLED is the most direct and effective method.
The existing structure for packaging the OLED is generally formed by bonding a glass or metal packaging cover plate with an OLED substrate through epoxy resin, and the epoxy resin can play a certain role in blocking, but still has the problems of high water vapor transmission rate, low light transmittance and the like.
Disclosure of Invention
An object of an embodiment of the present invention is to provide a silicon-containing monomer to solve the above problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a silicon-containing monomer has a general structural formula of formula 1:
in the formula, R 3 ～R 8 Wherein at least one group has a formula 2, and each of the remaining groups is independently at least one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, and a hydroxyl group:
n 1 、n 2 、n 3 、n 4 、n 5 are all natural numbers;
R 1 、R 2 and R 11 Independently alkyl of the same or different number of carbon atoms;
R 9 、R 10 and R 12 Independently hydrogen or methyl, is a binding site;
A 1 and A 2 Independently a group of any one of the formulae A001 to A003:
preferably, n is 2 、n 3 、n 4 Are not more than 1.
Preferably, R 11 Is C1-C10 alkyl.
Preferably, the structure of the silicon-containing monomer is at least one of the following structural formulas:
it is another object of an embodiment of the present invention to provide an encapsulating composition, which includes a photo-curable monomer and a photo-crosslinking initiator, and further includes the above silicon-containing monomer.
Preferably, the weight percentage of the photocuring monomer in the packaging composition is 15-75%, the weight percentage of the silicon-containing monomer is 15-80%, and the weight percentage of the photocrosslinking initiator is 1-10%.
Preferably, the photo-crosslinking initiator is at least one of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), 2-hydroxy-2-methyl-1-phenylpropanone (1173), 2,4, 6-trimethylbenzoyl diphenyl phosphonite.
Preferably, the photo-curable monomer is an acrylate.
Specifically, the photo-curable monomer is at least one of monofunctional (meth) acrylate of C1 to C30 monohydric or polyhydric alcohol, difunctional (meth) acrylate of C2 to C30 monohydric or polyhydric alcohol, and polyfunctional (meth) acrylate of C3 to C30 monohydric or polyhydric alcohol.
Preferably, the monofunctional (meth) acrylate may be Lauryl Acrylate (LA), ethoxyethoxyethyl acrylate [ (EOEOEA) -KPX A007], Butyl Acrylate (BA), hydroxyethyl acrylate and isobornyl acrylate, ethoxylated tetrahydrofurfuryl acrylate [ (THF (EO) A) -KPX A015], methacrylate phosphate and isobornyl methacrylate, and the like.
The bifunctional (meth) acrylates are mostly diol structures, and mainly include ethylene glycol diacrylates, propylene glycol diacrylates and other diol diacrylates. The concrete structure is as follows: diethylene glycol diacrylate (DEGDA), triethylene glycol diacrylate (TEGDA), ethylene glycol diacrylate, polyethylene glycol (200) diacrylate [ PEG (200) DA ], polyethylene glycol (400) diacrylate [ PEG (400) DA ], polyethylene glycol (600) diacrylate [ PEG (600) DA ], neopentyl glycol diacrylate, propoxy neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate (HDDA), 1, 4-butanediol diacrylate (BDDA), 20 (ethoxy) bisphenol a diacrylate [ bpa (eo)20DA ], glycerol diacrylate (TPGDA).
The multifunctional (meth) acrylate may be trimethylolpropane triacrylate (TMPTA), pentaerythritol triacrylate (PETA), trimethylolpropane triol triacrylate (TMPTMA), trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, pentaerythritol triacrylate and propoxylated pentaerythritol triacrylate, ditrimethylolpropane tetraacrylate, triethylene glycol dimethacrylate, long chain aliphatic glycidyl ether acrylate, dipentaerythritol hexaacrylate, tripropylene glycol diacrylate, phthalic acid diethanol diacrylate (PDDA), ethoxylated trimethylolpropane triacrylate [ TMP (EO) TMA ], propoxylated trimethylolpropane triacrylate [ TMP PO) TMA ], propoxylated glycerol triacrylate [ G (PO) TA ], Tris (2-hydroxyethyl) isocyanurate triacrylate, ethoxylated neopentyl glycol methoxy monoacrylate [ TMP (PO) MEDA ], and the like.
It is another object of the embodiments of the present invention to provide an encapsulation structure, which includes an organic layer, wherein the organic layer partially or completely contains the above encapsulation composition.
It is another object of embodiments of the present invention to provide an optoelectronic device, which includes a functional structure and the above-mentioned package structure.
Preferably, the optoelectronic device may be any one of an electroluminescent device, a photoluminescent device, a lighting device, a light emitting diode, a solar cell, a thin film transistor, and a photodetector.
Compared with the prior art, the embodiment of the invention has the following beneficial effects:
compared with a monomer without benzene ring and silicon atom, the silicon-containing monomer provided by the embodiment of the invention has better heat resistance and transparency, and lower water vapor transmission rate and oxygen transmission rate, and on the other hand, the excessive shrinkage volume generated when the packaging composition is cured is reduced.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
The embodiment provides a method for manufacturing a package structure, which includes the following steps:
s1, weighing 20g of silicon-containing monomer 001, 75g of lauryl acrylate and 5g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, mixing, stirring for 80 hours at 50 ℃ in vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein, the structural formula of the silicon-containing monomer 001 is as follows:
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the sealing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and mixing the organic layer and the inorganic layer at an intensity of 100mW/cm 2 The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the thin film type packaging structure.
Example 2
The embodiment provides a method for manufacturing a package structure, which includes the following steps:
s1, weighing 20g of silicon-containing monomer 002, 75g of 1, 6-hexanediol diacrylate and 5g of 2-hydroxy-2-methyl-1-phenyl acetone, mixing, stirring for 80h at 50 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein, the structural formula of the silicon-containing monomer 002 is as follows:
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the sealing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and mixing the organic layer and the inorganic layer at an intensity of 100mW/cm 2 The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
And S4, coating the inorganic layer material on the organic layer by a CVD method to form another inorganic layer, thus obtaining the thin film type packaging structure.
Example 3
The embodiment provides a method for manufacturing a package structure, which includes the following steps:
s1, weighing 20g of silicon-containing monomer 003, 75g of diethylene glycol diacrylate and 5g of 2,4, 6-trimethylbenzoyl diphenyl phosphonite, mixing together, stirring for 80 hours at 50 ℃ under vacuum, then filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50; wherein, the structural formula of the silicon-containing monomer 003 is as follows:
s2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the sealing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and mixing the organic layer and the inorganic layer at an intensity of 100mW/cm 2 The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the thin film type packaging structure.
Example 4
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 1 only in that step S1 is: 30g of silicon-containing monomer 001, 60g of lauryl acrylate and 10g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide are weighed, mixed together, stirred for 80 hours at 50 ℃ under vacuum, then filtered by a syringe filter, detected by using a particle counter, and when the number of particles with the particle size of more than 0.5 μm is detected to be not more than 50, a packaged composition is obtained for later use.
Example 5
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 2 only in that step S1 is: weighing 30g of silicon-containing monomer 002, 60g of 1, 6-hexanediol diacrylate and 10g of 2-hydroxy-2-methyl-1-phenyl acetone, mixing together, stirring for 80h at 50 ℃ under vacuum, then filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50.
Example 6
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 3 only in that step S1 is: 30g of silicon-containing monomer 003, 60g of diethylene glycol diacrylate and 10g of 2,4, 6-trimethylbenzoyl diphenyl phosphonite are weighed out, mixed together, stirred for 80h at 50 ℃ under vacuum, filtered by means of a syringe filter, checked by means of a particle counter, and when no more than 50 particles with a particle size of more than 0.5 μm are detected, a packaged composition is obtained and ready for use.
Example 7
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 1 only in that step S1 is: 15g of silicon-containing monomer 001, 75g of lauryl acrylate, 5g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide and 5g of 2-hydroxy-2-methyl-1-phenylpropanone are weighed, mixed together, stirred for 80h at 50 ℃ under vacuum, filtered by a syringe filter, detected by a particle counter, and when no more than 50 particles with a particle size of more than 0.5 μm are detected, a packaged composition is obtained for use.
Example 8
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 1 only in that step S1 is: weighing 80g of silicon-containing monomer 001, 15g of lauryl acrylate and 5g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, mixing together, stirring for 80h at 50 ℃ under vacuum, then filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50.
Example 9
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 1 only in that step S1 is: 54g of silicon-containing monomer 001, 45g of lauryl acrylate and 1g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide are weighed and mixed together, stirred for 80 hours at 50 ℃ under vacuum, filtered by a syringe filter, detected by a particle counter, and when the number of particles with the particle size of more than 0.5 μm is detected to be not more than 50, a packaged composition is obtained for later use.
Example 10
This embodiment provides a method for manufacturing a package structure, which is different from embodiment 2 only in that step S1 is: 60g of silicon-containing monomer 002, 35g of lauryl acrylate and 5g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide are weighed and mixed together, stirred for 80 hours at 50 ℃ under vacuum, then filtered by a syringe filter, detected by a particle counter, and when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50, a packaging composition is obtained for later use.
Example 11
The embodiment provides a method for manufacturing a package structure, which includes the following steps:
s1, weighing 30g of silicon-containing monomer 002, 45g of 1, 6-hexanediol diacrylate, 20g of lauryl acrylate, 2g of 2-hydroxy-2-methyl-1-phenyl acetone, 2g of 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide and 1g of 2,4, 6-trimethylbenzoyl diphenyl phosphonite, mixing together, stirring for 70 hours at 45 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining an encapsulated composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50.
S2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3 ink-jet printing the sealing compositionSpraying onto the surface of the inorganic layer to form an organic layer, and applying an intensity of 90mW/cm 2 The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the thin film type packaging structure.
Example 12
The embodiment provides a method for manufacturing a package structure, which includes the following steps:
s1, weighing 55g of silicon-containing monomer 003, 40g of 1, 6-hexanediol diacrylate and 5g of 2-hydroxy-2-methyl-1-phenyl acetone, mixing together, stirring for 90 hours at 60 ℃ under vacuum, filtering by using a syringe filter, detecting by using a particle counter, and obtaining a packaging composition for later use when the number of particles with the particle size of more than 0.5 mu m is detected to be not more than 50.
S2, selecting silicon nitride as an inorganic layer material, and coating the inorganic layer material on the surface of the object to be packaged by a Chemical Vapor Deposition (CVD) method to form the inorganic layer.
S3, spraying the sealing composition on the surface of the inorganic layer by an ink-jet printer to form an organic layer, and using the intensity of 110mW/cm 2 The organic layer was irradiated with ultraviolet light for 10 seconds each time to harden the organic layer.
S4, coating the inorganic layer material on the organic layer by CVD method to form another inorganic layer, and obtaining the thin film type packaging structure.
Comparative example 1
This comparative example provides a method for manufacturing a package structure, which is different from example 1 only in that step S1 is: weighing 98g of lauryl acrylate and 2g of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, mixing together, stirring for 80h at 50 ℃ under vacuum, filtering with a syringe filter, detecting with a particle counter, and obtaining a packaging composition for later use when the number of particles with a particle size of more than 0.5 μm is not more than 50.
Test example:
first, the water vapor transmission rate of the package structures prepared in examples 1 to 6 and comparative example 1 was measured, and the measurement results are shown in table 1. Wherein, the detecting instrument: the manufacturer is a high-precision water vapor transmission rate tester with model number of AQUARAN2, manufactured by MOCON corporation (American Membrane health corporation); detection conditions are as follows: the temperature is 85 ℃, and the relative humidity is 85%; detection duration: for 24 hours.
Second, the light transmittance of the package structures prepared in examples 1 to 6 and comparative example 1 was measured, and the measurement results are shown in table 1. Wherein, the detecting instrument: a light transmittance tester; detection conditions are as follows: the temperature was 40 ℃ and the relative humidity was 85%.
TABLE 1
| Group of | Water vapor transmission rate (g/m) 2 ·d) | Light transmittance (%) |
| Example 1 | 4.8*10 -4 | 86 |
| Example 2 | 4.9*10 -4 | 85 |
| Example 3 | 4.3*10 -4 | 86 |
| Example 4 | 4.5*10 -4 | 87 |
| Example 5 | 4.8*10 -4 | 85 |
| Example 6 | 4.9*10 -4 | 87 |
| Comparative example 1 | 9.0*10 -3 | 86 |
As can be seen from table 1, examples 1 to 6 are different from comparative example 1 in that the silicon-containing monomers provided in examples 1 to 6 are added, and a comparison shows that the water vapor transmission rate of the package structure after the silicon-containing monomers provided in examples of the present invention are added is obviously lower than that of the package structure without the silicon-containing monomers provided in examples of the present invention; therefore, the photoelectric device packaged by the packaging structure can effectively isolate moisture, so that the service life of the photoelectric device can be prolonged.
In another embodiment of the present invention, there is also provided an optoelectronic device comprising a functional structure and the above-described encapsulation structure. Specifically, the optoelectronic device may be any one of an electroluminescent device, a photoluminescent device, a lighting device, a light emitting diode, a solar cell, a thin film transistor, and a photodetector, but is not limited thereto.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (9)
1. A silicon-containing monomer, wherein the structural formula of the silicon-containing monomer is formula 1:
in the formula, R 3 ～R 8 Wherein at least one group has a formula 2, and each of the remaining groups is independently at least one of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted hydroxyalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted lactone group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted glycidyl ether group, and a hydroxyl group:
n 1 、n 2 、n 3 、n 4 、n 5 all are natural numbers not greater than 1;
R 1 、R 2 and R 11 Independently alkyl of the same or different number of carbon atoms;
R 9 、R 10 and R 12 Independently hydrogen or methyl, is a binding site;
A 1 and A 2 Independently a group of any one of the formulae A001 to A003:
2. the silicon-containing monomer according to claim 1, wherein the monomer is selected from the group consisting of，R 11 Is C1-C10 alkyl.
3. The silicon-containing monomer according to claim 1, wherein the structure of the silicon-containing monomer is at least one of the following structural formulas:
4. an encapsulating composition comprising a photo-curable monomer and a photo-crosslinking initiator, characterized by further comprising a silicon-containing monomer according to any one of claims 1 to 3.
5. A packaging composition according to claim 4, wherein the photocurable monomer is present in an amount of 15-75% by weight, the silicon-containing monomer is present in an amount of 15-80% by weight, and the photo-crosslinking initiator is present in an amount of 1-10% by weight.
6. A packaging composition according to claim 4, wherein the photo-crosslinking initiator is at least one of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, 2-hydroxy-2-methyl-1-phenylpropanone, 2,4, 6-trimethylbenzoyl diphenylphosphinite.
7. A packaging composition according to claim 4, wherein the photocurable monomer is an acrylate.
8. An encapsulation structure comprising an organic layer, characterized in that said organic layer partially or totally comprises an encapsulation composition according to any one of claims 4 to 7.
9. An optoelectronic device comprising a functional structure, further comprising the encapsulation structure of claim 8.
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