CN114133877A - Photocuring composition glue containing large conjugated aromatic ring acrylic compound monomer and use method and application thereof - Google Patents
Photocuring composition glue containing large conjugated aromatic ring acrylic compound monomer and use method and application thereof Download PDFInfo
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- CN114133877A CN114133877A CN202111505810.9A CN202111505810A CN114133877A CN 114133877 A CN114133877 A CN 114133877A CN 202111505810 A CN202111505810 A CN 202111505810A CN 114133877 A CN114133877 A CN 114133877A
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- aromatic ring
- conjugated aromatic
- light
- acrylic compound
- large conjugated
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- -1 aromatic ring acrylic compound Chemical class 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000000178 monomer Substances 0.000 title claims abstract description 47
- 239000003292 glue Substances 0.000 title claims abstract description 45
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000010521 absorption reaction Methods 0.000 claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 238000001723 curing Methods 0.000 claims abstract description 18
- 238000004132 cross linking Methods 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 239000010408 film Substances 0.000 claims description 50
- 238000002834 transmittance Methods 0.000 claims description 21
- RAWPGIYPSZIIIU-UHFFFAOYSA-N [benzoyl(phenyl)phosphoryl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 RAWPGIYPSZIIIU-UHFFFAOYSA-N 0.000 claims description 15
- 238000007641 inkjet printing Methods 0.000 claims description 15
- 238000004806 packaging method and process Methods 0.000 claims description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 3
- FJKOQFIGFHTRRW-UHFFFAOYSA-N (2-methoxy-3-methylphenyl)-(3-methylphenyl)methanone Chemical compound COC1=C(C)C=CC=C1C(=O)C1=CC=CC(C)=C1 FJKOQFIGFHTRRW-UHFFFAOYSA-N 0.000 claims description 3
- RVWADWOERKNWRY-UHFFFAOYSA-N [2-(dimethylamino)phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1C(=O)C1=CC=CC=C1 RVWADWOERKNWRY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 238000007650 screen-printing Methods 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 150000004072 triols Chemical class 0.000 claims description 3
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000002346 layers by function Substances 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 2
- 229920006280 packaging film Polymers 0.000 abstract description 2
- 239000012785 packaging film Substances 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 1
- FQVOKXARZCJTIT-UHFFFAOYSA-N 2-bromopyrene Chemical compound C1=CC=C2C=CC3=CC(Br)=CC4=CC=C1C2=C43 FQVOKXARZCJTIT-UHFFFAOYSA-N 0.000 description 1
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 1
- WHGGVVHVBFMGSG-UHFFFAOYSA-N 9-bromo-10-phenylanthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1 WHGGVVHVBFMGSG-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/80—Constructional details
- H10K30/88—Passivation; Containers; Encapsulations
-
- 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
-
- 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 belongs to the technical field of organic films, and relates to photocuring composition glue containing a large conjugated aromatic ring acrylic monomer and a using method thereof. The light-cured composition glue comprises the following components in parts by weight: 2-85 parts of acrylic compound monomer with a large conjugated aromatic ring, 2-85 parts of light curable monomer and 0.1-8 parts of light crosslinking initiator. The glue adopts an acrylic compound monomer containing a large conjugated aromatic ring, and pi → pi transition absorption can be obtained by introducing an organic conjugated group so as to improve the absorption capacity of molecules to ultraviolet light; by changing the specific structure and the connection mode of the large conjugated group, the interaction among the molecules of the packaging film can be changed, which is beneficial to optimizing the protection capability; by utilizing the light-cured composition glue, a flexible organic film with high ultraviolet curing efficiency and strong ultraviolet absorption capacity can be obtained, so that the damage of ultraviolet rays to an organic functional layer is reduced, and the flexible organic film with better property is obtained.
Description
Technical Field
The invention belongs to the technical field of organic films, and relates to photocuring composition glue containing a large conjugated aromatic ring acrylic compound monomer, and a use method and application thereof.
Background
With the rapid development of science and technology, flexible foldable and even rollable electronic devices are more and more paid more attention to the market, and especially smart devices such as televisions, computers, mobile phones and smart watches based on flexible organic light emitting diodes are more and more favored by consumers. In the use process of these products, in addition to the display effect, the service life of the products, which makes the products work reliably and stably, is one of the most critical indexes. In order to have the flexible, foldable and curled characteristic, organic molecular materials which are easily corroded by water vapor and oxygen in the air are used in the device, so that the service life of the device is greatly influenced by the water and oxygen isolating effect of device packaging. In order to prolong the service life, the device needs to be well encapsulated because the harmful erosion effect on organic molecular materials caused by the water vapor and oxygen entering the device must be effectively prevented.
At present, the commonly used packaging materials are inorganic materials, the flexibility and the water oxygen protection capability of the packaging materials are continuously improved, but still the satisfactory effect can not be achieved. The organic packaging material has intrinsic flexibility, is very suitable for preparing flexible devices, has changeable molecular structure, abundant material system types, wide raw material sources and lower preparation cost, and can well make up the defects of inorganic packaging materials. Therefore, organic encapsulation materials are one of the best materials for protecting flexible electronic devices from water and oxygen. However, molecules of currently used or reported organic encapsulating materials mainly consist of non-conjugated groups, and the formed encapsulating film has very poor ultraviolet absorption capability, so that ultraviolet can easily penetrate through the encapsulating layer to reach other organic functional layers in the device. Under the action of high-energy ultraviolet rays, molecules of an organic functional layer are easy to degrade, so that the performance, the service life and the like of a device are obviously reduced.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide photocuring composition glue containing a large conjugated aromatic ring acrylic compound monomer and a using method thereof.
In order to achieve the purpose, the invention provides the following technical scheme:
on one hand, the invention provides photocuring composition glue containing a large conjugated aromatic ring acrylic compound monomer, which comprises the following components in parts by weight: 2-85 parts of acrylic compound monomer with a large conjugated aromatic ring, 2-85 parts of light curable monomer and 0.1-8 parts of light crosslinking initiator.
Further, the structural general formula of the acrylic compound monomer with the large conjugated aromatic ring is as follows:
wherein, the substituent R1Is a hydrogen atom or an alkyl chain with the length of the carbon chain being 1-6; r2The alkyl chain is an alkyl chain with a carbon chain length of 1-6; r3Is a large conjugated aromatic ring.
Further, the large conjugated aromatic ring R3The structure of (a) includes at least one structure of the following general formula:
further, the large conjugated aromatic ring R3Comprises at least one derivative of phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran and carbazole compounds.
Further, the photocurable monomer includes at least one of: c1To C30Monofunctional (meth) acrylates of monoalcohols, C2To C30Di (meth) acrylates of dihydric, trihydric, tetrahydric or pentahydric alcohols, C3To C30Tri (meth) acrylates of triols, tetrols or pentols.
Further, the photo-crosslinking initiator is one or more of hydroxybenzophenone, benzoyldiphenylphosphine oxide, bis-benzoylphenylphosphine oxide, 4' -dichlorobenzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone, and 3,3' -dimethyl-2-methoxybenzophenone.
On the other hand, the invention also provides a using method of the photocuring composition glue containing the large conjugated aromatic ring acrylic compound monomer, which comprises the steps of firstly adopting a spin coating, ink-jet printing, screen printing or blade coating method to attach part or all of the photocuring composition glue on the surface of the organic electronic device; and irradiating the glue layer attached to the surface of the device by using light with the wavelength of 200-450 nm for 10-100 seconds to solidify the glue layer, and finally forming an organic film with the thickness of 25-80 microns.
Furthermore, the maximum absorption range of the organic film to ultraviolet light reaches 420nm, and the illumination curing rate is 91.3% -97.2%.
Furthermore, the transmittance of the organic thin film to light with the wavelength of 430-800 nm is 92.2% -96.3%.
In addition, the invention also provides application of the photocuring composition glue containing the large conjugated aromatic ring acrylic compound monomer, wherein part or all of the photocuring composition glue is photocured to form a compact film so as to prevent or relieve erosion damage of oxygen and water vapor to an organic light-emitting device, an organic photovoltaic device, an organic-inorganic hybrid perovskite light-emitting device or an organic-inorganic hybrid perovskite photovoltaic device.
Compared with the prior art, the technical scheme provided by the invention has the following beneficial effects: by adopting an acrylic compound monomer containing a large conjugated aromatic ring, pi → pi transition absorption can be obtained by introducing an organic conjugated group so as to improve the absorption capacity of molecules to ultraviolet light. In addition, the maximum absorption range of ultraviolet absorption can be effectively shifted from about 200nm to about 420nm by extending the conjugation length to form a large conjugation group, so that high-intensity effective absorption of the whole ultraviolet region is formed, and ultraviolet light is prevented from penetrating through the packaging protection film to enter the device to damage organic functional molecules.
In addition, the interaction among the molecules of the packaging film can be changed by changing the specific structure and the connection mode of the large conjugated group, thereby being beneficial to further optimizing the protection capability; by reasonably introducing 0.1-8 parts of photo-crosslinking initiator, the photo-curing crosslinking rate can be promoted, the preparation time is reduced, the energy is saved, and the cost is reduced; the large conjugated group used in the photocuring composition glue is a common chemical product produced in an industrial large-scale manner, the yield is high, the cost is low, the whole preparation process is simple to operate, and the photocuring composition glue can be rapidly cured into a compact and uniform organic film which is strong in ultraviolet absorption capacity and high in visible light transmittance by using a common cheap common ultraviolet light source.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the present invention is further described in detail with reference to the following examples.
On one hand, the invention provides photocuring composition glue containing a large conjugated aromatic ring acrylic compound monomer, which can be used as an ultraviolet curable material of an electronic device packaging layer and can be applied to waterproof and oxygen-resistant packaging of electronic products such as organic light-emitting diodes, organic solar cells, perovskite solar cells or integrated circuit boards. The light-cured composition glue comprises the following components in parts by weight: 2-85 parts of acrylic compound monomer with a large conjugated aromatic ring, 2-85 parts of light curable monomer and 0.1-8 parts of light crosslinking initiator.
Further, the structural general formula of the acrylic compound monomer containing the large conjugated aromatic ring is as follows:
wherein, the substituent R1Is a hydrogen atom or an alkyl chain with the length of the carbon chain being 1-6; r2The alkyl chain is an alkyl chain with a carbon chain length of 1-6; r3The derivative is a large conjugated aromatic ring, comprises compounds such as phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran, carbazole and the like, and is represented by at least one of the following structures:
further, the photocurable monomer includes at least one of the following: c1To C30Monofunctional (meth) acrylates of monoalcohols, C2To C30Di (meth) acrylates of dihydric, trihydric, tetrahydric or pentahydric alcohols, C3To C30Tri (meth) acrylates of triols, tetrols or pentols.
Further, the photo-crosslinking initiator is one or more of hydroxybenzophenone, benzoyldiphenylphosphine oxide, bis-benzoylphenylphosphine oxide, 4' -dichlorobenzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone, and 3,3' -dimethyl-2-methoxybenzophenone.
Preferably, the photocrosslinking initiator is bis-benzoylphenylphosphine oxide, and when the bis-benzoylphenylphosphine oxide is used as the initiator, the curing rate can reach more than 91% within 100 s.
Preferably, the content of the photo-crosslinking initiator is controlled to be 0.5-3.0 parts, so that the crosslinking curing time and the visible light transmittance of the film can be well balanced; because the amount of the photo-crosslinking initiator is too small, the crosslinking time is longer; if the amount of the photo-crosslinking initiator is too much, the light transmittance of the film to visible light is reduced due to the dark color of the crosslinking agent.
On the other hand, the invention also provides a preparation method of the photocuring composition glue, which comprises the following steps: according to the weight parts, an acrylic compound monomer containing a large conjugated aromatic ring, a polyol acrylic compound monomer and a photo-crosslinking initiator are placed in a brown glass container, stirred and mixed at room temperature until the photo-crosslinking initiator is dissolved, and the preparation of the photo-curing composition glue is completed.
In addition, the application method of the light-cured composition glue is as follows: the light-cured composition glue is uniformly attached to the surface of the electronic device to be encapsulated by one of ink-jet printing, spin coating, screen printing or blade coating, and then the organic protective film is promoted to be formed by ultraviolet lamp irradiation.
The method adopts an ink-jet printing mode to print the photocuring composition glue into a liquid film with a certain shape, and then adjusts the power of an ultraviolet lamp to be 10-500 mW/cm2And irradiating for 10-100 s for photocuring to obtain an organic thin film protective layer with a thickness of 25-80 μm.
Tests show that after the photocuring composition glue is irradiated and cured by ultraviolet light or blue light with the wavelength of 200-450 nm to form an organic film protective layer, the photocuring composition glue has the curing rate of 91.0-97.2% and the light transmittance of 90-96.3% to the wavelength of 430-800 nm.
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all of the embodiments. The components of embodiments of the present invention generally described and illustrated herein may be arranged and designed in a wide variety of different configurations. Thus, the following detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
In this example, 2- (pyrene-2-yloxy) ethyl methacrylate is used as the acrylic compound monomer containing a large conjugated aromatic ring, and the synthetic route is as follows:
the specific preparation process is as follows:
adding 28.2g of 2-bromopyrene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate into a reaction bottle in a nitrogen atmosphere, heating to 130 ℃, stirring for 24 hours, cooling the reaction mixture to room temperature, washing with water and extracting with dichloromethane to obtain an organic layer;
drying the organic layer with anhydrous sodium sulfate, concentrating to remove dichloromethane, and purifying the residue with silica gel column to obtain 24.5g 2- (pyrene-2-yloxy) ethan-1-ol;
then, the obtained 2- (pyrene-2-yloxy) ethan-1-ol and 14.8g of methacryloyl chloride were dissolved in 200mL of dry pyridine, stirred at room temperature under nitrogen atmosphere for 24 hours, concentrated, and the residue was purified by a silica gel column to obtain 20.7g of 2- (pyrene-2-yloxy) ethyl methacrylate with a yield of 64%.
5.0g of 2- (pyrene-2-yloxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle and stirred at room temperature in the dark for 2 hours to obtain a photocurable composition glue (I).
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 56 mu m; the curing rate of the film is 92.4%, the maximum ultraviolet absorption range reaches 380nm, and the light transmittance to the wavelength of 430-800 nm is 94.6%.
Example 2
5.0g of 2- (pyrene-2-yloxy) ethyl methacrylate, 5.0g of glycerol diacrylate and 0.3g of bis-benzoylphenylphosphine oxide, prepared as described in example 1, were placed in a brown glass bottle and stirred at room temperature for 2 hours in the dark to give a photocurable composition glue (II).
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 72 mu m; the curing rate of the film is 91.9%, the maximum ultraviolet absorption range reaches 410nm, and the light transmittance to the wavelength of 430-800 nm is 93.9%.
Example 3
In this example, the acrylic compound monomer containing a large conjugated aromatic ring is 2- ((10-phenylanthracen-9-yl) oxy) ethyl methacrylate, and the synthetic route is as follows:
the specific preparation process is as follows:
adding 33.2g of 9-bromo-10-phenylanthracene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate into a reaction flask in a nitrogen atmosphere, heating to 130 ℃, stirring for 24 hours, cooling the reaction mixture to room temperature, washing with water and extracting with dichloromethane to obtain an organic layer;
the organic layer was dried over anhydrous sodium sulfate and concentrated to remove methylene chloride, and the residue was purified by a silica gel column to obtain 17.9g of 2- ((10-phenylanthren-9-yl) oxy) ethan-1-ol;
subsequently, the obtained 2- ((10-phenylanthren-9-yl) oxy) ethan-1-ol and 8.9g of methacryloyl chloride were dissolved in 200mL of dry pyridine, stirred at room temperature under a nitrogen atmosphere for 24 hours, and then concentrated, and the residue was purified by a silica gel column to obtain 13.7g of ethyl 2- ((10-phenylanthren-9-yl) oxy) methacrylate in a yield of 63%.
4.0g of ethyl 2- ((10-phenylanthen-9-yl) oxy) methacrylate, 8.0g of glycerol diacrylate and 0.25g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle and stirred at room temperature for 2 hours in the dark to give a photocurable composition paste (III).
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 45 mu m; the curing rate of the film is 96.2%, the maximum ultraviolet absorption range reaches 360nm, and the light transmittance to the wavelength of 430-800 nm is 96.3%.
Example 4
4.0g of ethyl 2- ((10-phenylanthen-9-yl) oxy) methacrylate prepared in example 3, 4.0g of glycerol diacrylate and 0.25g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle and, after stirring at room temperature for 2h in the dark, a photocurable composition paste (IV) was obtained.
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 52 mu m; the film curing rate is 95.3%, and the maximum ultraviolet absorptionThe range of the light transmittance is 368nm, and the light transmittance to the wavelength of 430-800 nm is 95.9%.
Example 5
In this embodiment, the acrylic compound monomer containing a large conjugated aromatic ring is 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate, and the synthetic route thereof is as follows:
the specific preparation process is as follows:
adding 32.1g of 9- (4-bromophenyl) -9H-carbazole, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate into a reaction bottle in a nitrogen atmosphere, heating to 130 ℃, stirring for 24 hours, cooling the reaction mixture to room temperature, washing with water, and extracting with dichloromethane to obtain an organic layer;
drying the organic layer with anhydrous sodium sulfate, concentrating to remove dichloromethane, purifying the residue with silica gel column to obtain 22.9g of 2- (4- (9H-carbazole-9-yl) phenoxy) ethan-1-ol;
subsequently, the obtained 2- (4- (9H-carbazol-9-yl) phenoxy) ethan-1-ol and 8.9g of methacryloyl chloride were dissolved in 200mL of dried pyridine, stirred at room temperature under a nitrogen atmosphere for 24 hours, concentrated, and the residue was purified by a silica gel column to obtain 19.3g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate with a yield of 69%.
5.0g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle and stirred at room temperature in the dark for 2 hours to obtain a photocurable composition glue (V).
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100 seconds by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 61 mu m; the curing rate of the film is 93.3%, the maximum ultraviolet absorption range reaches 350nm, and the light transmittance to the wavelength of 430-800 nm is 95.2%.
Example 6
5.0g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate prepared in example 5, 5.0g of glycerol diacrylate and 0.25g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle, and after stirring at room temperature for 2 hours in the dark, a photocurable composition paste (VI) was obtained.
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 69 mu m; the curing rate of the film is 92.5 percent, the maximum ultraviolet absorption range reaches 378nm, and the light transmittance to the wavelength of 430-800 nm is 94.7 percent.
Example 7
10.0g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate prepared in example 5, 0.25g of glycerol diacrylate and 0.25g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle, and after stirring at room temperature for 2 hours in the dark, a photocurable composition paste (VII) was obtained.
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 76 mu m; the curing rate of the film is 91.9%, the maximum ultraviolet absorption range reaches 392nm, and the light transmittance to the wavelength of 430-800 nm is 93.3%.
Example 8
In this example, 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate is used as the acrylic compound monomer containing a large conjugated aromatic ring, and the synthetic route is as follows:
the specific preparation process is as follows:
adding 26.2g of 2-bromodibenzo [ b, d ] thiophene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate into a reaction bottle in a nitrogen atmosphere, heating to 130 ℃, stirring for 24 hours, cooling the reaction mixture to room temperature, washing with water and extracting with dichloromethane to obtain an organic layer;
the organic layer was dried over anhydrous sodium sulfate, then, methylene chloride was removed by concentration, and the residue was purified by a silica gel column to obtain 16.9g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethan-1-ol;
subsequently, the obtained 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethan-1-ol and 10.8g of methacryloyl chloride were dissolved in 200mL of dry pyridine, and stirred at room temperature under a nitrogen atmosphere for 24 hours, followed by concentration, and the residue was purified by a silica gel column to obtain 13.6g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate with a yield of 63%.
5.0g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle, and stirred at room temperature in the dark for 2 hours to obtain a photocurable composition paste (eight).
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film, wherein the thickness of the film is 73 micrometers; the curing rate of the film is 93.9%, the maximum ultraviolet absorption range reaches 396nm, and the light transmittance to the wavelength of 430-800 nm is 92.2%.
Example 9
5.0g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate prepared in example 8, 5.0g of glycerol diacrylate and 0.25g of bis-benzoylphenylphosphine oxide were added to a brown glass bottle, and after stirring at room temperature for 2 hours in the dark, a photocurable composition paste (nine) was obtained.
Then, the ink was applied to the surface of the substrate by ink-jet printing, followed by passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 80 mu m; the curing rate of the film is 91.8%, the maximum ultraviolet absorption range reaches 417nm, and the light transmittance to the wavelength of 430-800 nm is 91.3%.
Example 10
12.0g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate prepared in example 8, 0.15g of glycerol diacrylate and 0.35g of bis-benzoylphenylphosphine oxide were charged into a brown glass bottle, and after stirring at room temperature for 2 hours in the dark, a photocurable composition paste (ten) was obtained.
Then, the user can use the device to perform the operation,coating on the surface of the substrate by ink-jet printing, and passing 10mW/cm2Irradiating the substrate for 100s by using an ultraviolet lamp to cure the substrate to form an organic packaging barrier film with the film thickness of 80 mu m; the curing rate of the film is 91.1%, the maximum ultraviolet absorption range reaches 428nm, and the light transmittance to the wavelength of 430-800 nm is 90.9%.
The optical performance evaluation method for the organic encapsulation barrier films formed in the above examples 1 to 10 was as follows:
the photocuring rate: the glue of this composition and the cured optical film were measured at 1635cm using FT-IR (Nicolet iS50, Thermo-Fisher)-1(C ═ C) and 1720cm-1Absorption peak intensity near (C ═ O).
The photocuring rate was as follows: a photocuring rate (%) |1- (F/S) | x 100; wherein F is 1635cm of the cured optical film with high refractive index-1The intensity of the absorption peak nearby is 1720cm-1The ratio of the intensities of nearby absorption peaks; s is 1635cm of the composition-1The intensity of the absorption peak nearby is 1720cm-1Ratio of the intensities of the nearby absorption peaks.
Light transmittance: forming a sample from the composition by ink-jet printing, followed by ultraviolet curing to form a photocurable film; and measuring the light transmittance of the cured film in a visible light range of 430-800 nm by using an ultraviolet spectrophotometer.
In combination with the above evaluation manner, the photocuring rate and the light transmittance of the organic encapsulation barrier film formed by the photocuring composition glue prepared in embodiments 1 to 10 of the present invention are detailed in the following table, in which a represents an acrylic compound monomer containing a large conjugated aromatic ring, B represents a photocurable monomer, and C represents a photocrosslinking initiator.
According to the experimental data in the table, on the premise that the content of the acrylic compound monomer A containing the large conjugated aromatic ring is not changed, the content of the light-curable monomer B is increased, so that the light curing rate and the light transmittance of the glue can be enhanced; according to the above examples 1-10, in combination with actual production requirements, the final preferred glue components of the photocurable composition are as follows: 4 parts of acrylic compound monomer A containing a large conjugated aromatic ring, 8 parts of light-curable monomer B and 0.25 part of light crosslinking initiator C.
In conclusion, the photocuring composition glue containing the large conjugated aromatic ring acrylic monomer provided by the invention can enhance the ultraviolet light absorption capacity of the monomer, promote the photocuring crosslinking process, expand the ultraviolet light absorption range of the cured film and enhance the protection capacity of the cured film on an encapsulated object.
The above description is only for the details of the technical solutions of the present invention, so that those skilled in the art can understand or implement the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention.
It is to be understood that the present invention is not limited to what has been described above, and that various modifications and changes may be made without departing from the scope thereof. The scope of the invention is limited only by the appended claims.
Claims (10)
1. The photocuring composition glue containing the large conjugated aromatic ring acrylic compound monomer is characterized by comprising the following components in parts by weight: 2-85 parts of acrylic compound monomer with a large conjugated aromatic ring, 2-85 parts of light curable monomer and 0.1-8 parts of light crosslinking initiator.
2. The photocurable composition glue containing a large conjugated aromatic ring acrylic compound monomer according to claim 1, wherein the structural general formula of the large conjugated aromatic ring acrylic compound monomer is as follows:
wherein, the substituent R1Is a hydrogen atom or a carbon chain lengthIn a 1-6 alkyl chain; r2The alkyl chain is an alkyl chain with a carbon chain length of 1-6; r3Is a large conjugated aromatic ring.
3. The photocurable composition glue containing a large conjugated aromatic ring acrylic compound monomer according to claim 2, wherein the large conjugated aromatic ring R3The structure of (a) includes at least one structure of the following general formula:
4. the photocurable composition glue containing a large conjugated aromatic ring acrylic compound monomer according to claim 2, wherein the large conjugated aromatic ring R3Comprises at least one derivative of phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran and carbazole compounds.
5. The photocurable composition glue containing a large conjugated aromatic ring acrylic compound monomer according to claim 1, wherein the photocurable monomer comprises at least one of the following: c1To C30Monofunctional (meth) acrylates of monoalcohols, C2To C30Di (meth) acrylates of dihydric, trihydric, tetrahydric or pentahydric alcohols, C3To C30Tri (meth) acrylates of triols, tetrols or pentols.
6. The photocurable composition glue containing a macro-conjugated aromatic ring acrylic compound monomer according to claim 1, wherein the photocrosslinking initiator is one or more of hydroxybenzophenone, benzoyldiphenylphosphine oxide, bis-benzoylphenylphosphine oxide, 4' -dichlorobenzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone, and 3,3' -dimethyl-2-methoxybenzophenone.
7. A method for using photocuring composition glue containing a large conjugated aromatic ring acrylic compound monomer is characterized in that the photocuring composition glue of any one of claims 1 to 6 is attached to the surface of an organic electronic device by adopting a spin coating, ink-jet printing, screen printing or blade coating method; and irradiating the glue layer attached to the surface of the device by using light with the wavelength of 200-450 nm for 10-100 seconds to solidify the glue layer, and finally forming an organic film with the thickness of 25-80 microns.
8. The use method of claim 7, wherein the maximum absorption range of the organic film to ultraviolet light is up to 420nm, and the light curing rate is 91.3% -97.2%.
9. The use method according to claim 7, wherein the transmittance of the organic thin film to light having a wavelength of 430 to 800nm is 92.2 to 96.3%.
10. The application of the light-cured composition glue containing the large conjugated aromatic ring acrylic compound monomer according to any one of claims 1 to 6 in waterproof and oxygen-resistant packaging of organic light-emitting devices, organic photovoltaic devices, organic-inorganic hybrid perovskite light-emitting devices or organic-inorganic hybrid perovskite photovoltaic devices.
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| CN115044244A (en) * | 2022-06-02 | 2022-09-13 | 西安思摩威新材料有限公司 | Packaging ink composition with low curing shrinkage rate and preparation method thereof |
| CN115433145A (en) * | 2022-09-16 | 2022-12-06 | 西安思摩威新材料有限公司 | Compound for packaging thin film, organic thin film packaging composition, packaging film and application |
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| JP2016117671A (en) * | 2014-12-19 | 2016-06-30 | 大阪ガスケミカル株式会社 | (meth) acrylate compound having anthracene skeleton and cured product thereof |
| CN112322195A (en) * | 2020-11-03 | 2021-02-05 | 西安思摩威新材料有限公司 | Ultraviolet curing composition glue and using method and application thereof |
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| CN101910348A (en) * | 2007-10-30 | 2010-12-08 | 3M创新有限公司 | High refractive index adhesives |
| JP2016117671A (en) * | 2014-12-19 | 2016-06-30 | 大阪ガスケミカル株式会社 | (meth) acrylate compound having anthracene skeleton and cured product thereof |
| CN112322195A (en) * | 2020-11-03 | 2021-02-05 | 西安思摩威新材料有限公司 | Ultraviolet curing composition glue and using method and application thereof |
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| CN115044244A (en) * | 2022-06-02 | 2022-09-13 | 西安思摩威新材料有限公司 | Packaging ink composition with low curing shrinkage rate and preparation method thereof |
| CN115044244B (en) * | 2022-06-02 | 2023-09-19 | 西安思摩威新材料有限公司 | Low-curing-shrinkage ink composition for packaging and preparation method thereof |
| CN115433145A (en) * | 2022-09-16 | 2022-12-06 | 西安思摩威新材料有限公司 | Compound for packaging thin film, organic thin film packaging composition, packaging film and application |
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