CN114133877B - Photo-curing composition glue containing large conjugated aromatic ring acrylic acid compound monomer, and use method and application thereof - Google Patents
Photo-curing composition glue containing large conjugated aromatic ring acrylic acid compound monomer, and use method and application thereof Download PDFInfo
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- CN114133877B CN114133877B CN202111505810.9A CN202111505810A CN114133877B CN 114133877 B CN114133877 B CN 114133877B CN 202111505810 A CN202111505810 A CN 202111505810A CN 114133877 B CN114133877 B CN 114133877B
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- -1 aromatic ring acrylic acid compound Chemical class 0.000 title claims abstract description 53
- 239000003292 glue Substances 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 43
- 239000000178 monomer Substances 0.000 title claims abstract description 42
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000010521 absorption reaction Methods 0.000 claims abstract description 28
- 238000004132 cross linking Methods 0.000 claims abstract description 20
- 238000001723 curing Methods 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 239000010408 film Substances 0.000 claims description 56
- 238000004806 packaging method and process Methods 0.000 claims description 24
- 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
- 230000001678 irradiating effect Effects 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 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
- 238000007641 inkjet printing Methods 0.000 claims description 6
- 239000010410 layer Substances 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 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
- 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
- 239000011241 protective layer Substances 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
- 238000010345 tape casting Methods 0.000 claims description 3
- 150000004072 triols Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 239000010409 thin film Substances 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
- 239000002346 layers by function Substances 0.000 abstract description 3
- 229920006280 packaging film Polymers 0.000 abstract description 3
- 239000012785 packaging film Substances 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000003993 interaction Effects 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 230000004888 barrier function Effects 0.000 description 20
- 238000003756 stirring Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 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
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000005538 encapsulation Methods 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
- 230000007547 defect Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 230000001681 protective effect Effects 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 230000021615 conjugation Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 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
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the technical field of organic films, and relates to a photo-curing composition glue containing a large conjugated aromatic ring acrylic monomer and a use method thereof. The photo-curing composition glue comprises the following components in parts by weight: 2 to 85 parts of large conjugated aromatic ring acrylic compound monomer, 2 to 85 parts of photo-curable monomer and 0.1 to 8 parts of photo-crosslinking initiator. The glue adopts an acrylic acid compound monomer containing a large conjugated aromatic ring, and can obtain pi-pi transition absorption by introducing an organic conjugated group so as to improve the absorption capacity of molecules to ultraviolet light; the interaction between molecules of the packaging film can be changed by changing the specific structure and the connection mode of the large conjugated group, which is beneficial to optimizing the protection capability; the light-cured composition glue can be used for obtaining the flexible organic film with high ultraviolet curing efficiency and strong ultraviolet absorption capacity so as to reduce the damage of ultraviolet rays to the organic functional layer, thereby obtaining the flexible organic film with better properties.
Description
Technical Field
The invention belongs to the technical field of organic films, and relates to a photo-curing composition glue containing a large conjugated aromatic ring acrylic acid compound monomer, a using method and application thereof.
Background
With the rapid development of science and technology, flexible foldable and even curled electronic devices are increasingly valued in the market, and especially intelligent devices such as televisions, computers, mobile phones and intelligent watches based on flexible organic light emitting diodes are increasingly favored by consumers. In the use process of the products, besides the display effect, the service life of the products for reliably and stably working is one of the most critical indexes. In order to have the characteristic of flexible folding and curling, 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 isolation effect of the device package. In order to prolong the service life, the water vapor and oxygen must be effectively prevented from entering the device to generate harmful erosion effect on the organic molecular materials, so that the device needs to be well packaged.
At present, the common packaging material is an inorganic material, the flexibility and the water-oxygen protection capability of which are continuously improved, but the satisfactory effect still cannot be achieved. The organic packaging material has intrinsic flexibility, is very suitable for preparing flexible devices, has changeable material molecular structure, rich 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 currently one of the best materials to protect flexible electronic devices from attack by water and oxygen. However, the organic packaging material molecules used or reported at present mainly consist of non-conjugated groups, and the formed packaging film has very poor ultraviolet absorption capability, so that ultraviolet rays can easily penetrate through the packaging layer to reach other organic functional layers in the device. Under the action of high-energy ultraviolet rays, the molecules of the organic functional layer are easy to degrade, so that the performance of the device, the service life and the like are obviously reduced.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a photo-curing composition glue containing a large conjugated aromatic ring acrylic acid compound monomer and a using method thereof.
In order to achieve the above purpose, the present invention provides the following technical solutions:
in one aspect, the invention provides a photo-curing composition glue containing a large conjugated aromatic ring acrylic compound monomer, which comprises the following components in parts by weight: 2 to 85 parts of large conjugated aromatic ring acrylic compound monomer, 2 to 85 parts of photo-curable monomer and 0.1 to 8 parts of photo-crosslinking initiator.
Further, the structural general formula of the large conjugated aromatic ring acrylic acid compound monomer is as follows:
wherein the substituents R 1 Is hydrogen sourceThe length of the son or carbon chain is 1-6 alkyl chains; r is R 2 Is an alkyl chain with a carbon chain length of 1-6; r is R 3 Is a large conjugated aromatic ring.
Further, the large conjugated aromatic ring R 3 Comprises at least one structure in the following general formula:
further, the large conjugated aromatic ring R 3 Comprises at least one derivative of phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran and carbazole compounds.
Further, the photocurable monomer includes at least one of the following: c (C) 1 To C 30 Monofunctional (meth) acrylic esters of monohydric alcohols, C 2 To C 30 Di (meth) acrylic acid esters of dihydric, trihydric, tetrahydric or pentahydric alcohols, C 3 To C 30 Tri (meth) acrylic acid esters of triols, tetrols or pentaols.
Further, the photo-crosslinking initiator is one or more of hydroxybenzophenone, benzoyl diphenyl phosphine oxide, dibenzoyl phenyl phosphine oxide, 4' -dichloro benzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone and 3,3' -dimethyl-2-methoxy benzophenone.
On the other hand, the invention also provides a use method of the photo-curing composition glue containing the large conjugated aromatic ring acrylic acid compound monomer, wherein the photo-curing composition glue is firstly adhered to the surface of the organic electronic device by adopting a spin coating, ink-jet printing, screen printing or knife coating method; and then irradiating the glue layer attached to the surface of the device by using light with the wavelength of 200-450 nm to solidify the glue layer, wherein the irradiation time is between 10 and 100 seconds, and finally forming the organic film with the thickness of 25-80 mu m.
Further, the maximum absorption range of the organic film to ultraviolet light reaches 420nm, and the light curing rate is 91.3% -97.2%.
Further, the organic thin film has a transmittance of 92.2 to 96.3% for light having a wavelength of 430 to 800 nm.
In addition, the invention also provides application of the photo-curing composition glue containing the large conjugated aromatic ring acrylic compound monomer, and the photo-curing composition glue is partially or completely cured by light to form a compact film so as to prevent or relieve corrosion 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: the method adopts the acrylic acid compound monomer containing large conjugated aromatic ring, and can obtain pi-pi transition absorption by introducing organic conjugated groups 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 prolonging the conjugation length to form a large conjugated group, so that high-strength effective absorption of the whole ultraviolet light region is formed, and ultraviolet light is prevented from penetrating into the device through the encapsulation protective film to damage organic functional molecules.
In addition, the specific structure and the connection mode of the large conjugated groups are changed, so that the interaction among molecules of the packaging film can be changed, and the protection capability can be further optimized; 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 photo-curing composition glue adopts large conjugated groups as chemical products which are commonly produced in industrial scale, has high yield and low cost, is simple to operate in the whole preparation process, and can be rapidly cured into a compact uniform organic film with strong ultraviolet absorption capability and high visible light transmittance by utilizing a common low-cost common ultraviolet light source.
Detailed Description
The present invention will be described in further detail with reference to examples for better understanding of the technical aspects of the present invention by those skilled in the art.
On one hand, the invention provides photo-curing composition glue containing a large conjugated aromatic ring acrylic acid 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-blocking packaging of electronic products such as organic light-emitting diodes, organic solar cells, perovskite solar cells or integrated circuit boards. The photo-curing composition glue comprises the following components in parts by weight: 2 to 85 parts of large conjugated aromatic ring acrylic compound monomer, 2 to 85 parts of photo-curable monomer and 0.1 to 8 parts of photo-crosslinking initiator.
Further, the structural general formula of the large conjugated aromatic ring-containing acrylic acid compound monomer is as follows:
wherein the substituents R 1 Is hydrogen atom or alkyl chain with carbon chain length of 1-6; r is R 2 Is an alkyl chain with a carbon chain length of 1-6; r is R 3 Derivatives of compounds which are large conjugated aromatic rings including phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran, carbazole, and the like, are represented by at least one of the following various structures:
further, the photocurable monomer includes at least one of the following: c (C) 1 To C 30 Monofunctional (meth) acrylic esters of monohydric alcohols, C 2 To C 30 Di (meth) acrylic acid esters of dihydric, trihydric, tetrahydric or pentahydric alcohols, C 3 To C 30 Tri (meth) acrylic acid esters of triols, tetrols or pentaols.
Further, the photo-crosslinking initiator is one or more of hydroxybenzophenone, benzoyl diphenyl phosphine oxide, dibenzoyl phenyl phosphine oxide, 4' -dichloro benzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone and 3,3' -dimethyl-2-methoxy benzophenone.
Preferably, the photo-crosslinking initiator is dibenzoylphenylphosphine oxide, and the curing rate can reach more than 91% within 100s when the dibenzoylphenylphosphine oxide is used as the initiator.
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 photo-crosslinking initiator is too little, the crosslinking time is longer; too much photo-crosslinking initiator reduces the light transmittance of the film to visible light due to the darker color of the crosslinking agent itself.
On the other hand, the invention also provides a preparation method of the photo-curing composition glue, which comprises the following steps: according to the weight portions, the acrylic acid compound monomer containing the large conjugated aromatic ring, the polyalcohol acrylic acid compound monomer and the photo-crosslinking initiator are placed in a brown glass container and stirred and mixed at room temperature until the photo-crosslinking initiator is dissolved, thus completing the preparation of the photo-curing composition glue.
In addition, the use method of the photo-curing composition glue is as follows: the light-cured composition glue is uniformly adhered to the surface of an electronic device to be packaged by one of ink-jet printing, spin coating, screen printing or knife coating, and then the organic protective film is promoted to be formed by irradiation of an ultraviolet lamp.
The invention adopts an ink-jet printing mode to print the photo-curing composition glue into a liquid film with a certain shape, and then adjusts the power of an ultraviolet lamp to be 10-500 mW/cm 2 And irradiating for 10-100 s to perform photo-curing to obtain an organic film protective layer with the thickness of 25-80 mu m.
Through tests, the light-cured composition glue has a curing rate of 91.0-97.2% and a light transmittance of 90-96.3% to a wavelength of 430-800 nm after being cured by ultraviolet light or blue light with the wavelength of 200-450 nm to form an organic film protective layer.
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. The components of the 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 invention, as provided, 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 made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
In this example, 2- (pyren-2-yloxy) ethyl methacrylate was used as the monomer of the large conjugated aromatic ring-containing acrylic compound, and the synthetic route was as follows:
the preparation process is as follows:
28.2g of 2-bromopyrene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate are added into a reaction bottle under a nitrogen atmosphere, the reaction mixture is cooled to room temperature after being heated to 130 ℃ and stirred for 24 hours, and an organic layer is obtained by washing with water and extracting with dichloromethane;
the organic layer was dried over anhydrous sodium sulfate, concentrated to remove dichloromethane, and the residue was purified by a silica gel column to obtain 24.5g of 2- (pyren-2-yloxy) ethan-1-ol;
next, the obtained 2- (pyren-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, and then concentrated, and the residue was purified by a silica gel column to obtain 20.7g of 2- (pyren-2-yloxy) ethyl methacrylate in a yield of 64%.
In a brown glass bottle, 5.0g of 2- (pyren-2-yloxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of dibenzoylphenyl phosphine oxide were added, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (I) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the film thickness of 56 mu m; film and method for producing the sameThe curing rate is 92.4%, the maximum ultraviolet absorption range reaches 380nm, and the light transmittance for wavelengths of 430-800 nm is 94.6%.
Example 2
In a brown glass bottle, 5.0g of 2- (pyren-2-yloxy) ethyl methacrylate prepared in example 1, 5.0g of glycerol diacrylate and 0.3g of dibenzoylphenyl phosphine oxide were charged, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (II) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the substrate for 100s by an ultraviolet lamp to cure the substrate to form an organic packaging barrier film, wherein the thickness of the film is 72 mu m; the film curing rate is 91.9%, the maximum ultraviolet absorption range reaches 410nm, and the light transmittance for 430-800 nm wavelength is 93.9%.
Example 3
In this example, the acrylic monomer containing a large conjugated aromatic ring was ethyl 2- ((10-phenylanthracen-9-yl) oxy) methacrylate, and the synthetic route was as follows:
the preparation process is as follows:
33.2g of 9-bromo-10-phenylanthracene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate are added to a reaction flask under nitrogen atmosphere, the reaction mixture is cooled to room temperature after heating to 130 ℃ and stirring for 24 hours, and an organic layer is obtained by washing with water and extracting with dichloromethane;
the organic layer was dried over anhydrous sodium sulfate, concentrated to remove dichloromethane, and the residue was purified by a silica gel column to obtain 17.9g of 2- ((10-phenylanthracene-9-yl) oxy) ethan-1-ol;
next, the resulting 2- ((10-phenylanthracen-9-yl) oxy) ethan-1-ol was dissolved with 8.9g of methacryloyl chloride in 200mL of dried pyridine, stirred at room temperature under 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-phenylanthracen-9-yl) oxy) methacrylate in 63% yield.
In a brown glass bottle, 4.0g of ethyl 2- ((10-phenylanthracen-9-yl) oxy) methacrylate, 8.0g of glycerol diacrylate and 0.25g of dibenzoylphenylphosphine oxide were added, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (III) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the film thickness of 45 mu m; the film curing rate is 96.2%, the maximum ultraviolet absorption range reaches 360nm, and the light transmittance for 430-800 nm wavelength is 96.3%.
Example 4
In a brown glass bottle, 4.0g of ethyl 2- ((10-phenylanthracen-9-yl) oxy) methacrylate prepared in example 3, 4.0g of glycerol diacrylate and 0.25g of dibenzoylphenylphosphine oxide were added, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (IV) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the film thickness of 52 mu m; the film curing rate is 95.3%, the maximum ultraviolet absorption range reaches 368nm, and the light transmittance for 430-800 nm wavelength is 95.9%.
Example 5
In this example, the acrylic compound monomer containing a large conjugated aromatic ring was 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate, and the synthetic route was as follows:
the preparation process is as follows:
32.1g of 9- (4-bromophenyl) -9H-carbazole, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate were added to a reaction flask under nitrogen atmosphere, the reaction mixture was cooled to room temperature after heating to 130 ℃ and stirring for 24 hours, and an organic layer was obtained by washing with water and extracting with methylene chloride;
the organic layer was dried over anhydrous sodium sulfate, concentrated to remove dichloromethane, and the residue was purified by a silica gel column to obtain 22.9g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethan-1-ol;
next, the obtained 2- (4- (9H-carbazol-9-yl) phenoxy) ethan-1-ol and 8.9g of methacryloyl chloride were dissolved in 200mL of dry pyridine, and after stirring at room temperature under 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) ethan-methacrylate in 69% yield.
In a brown glass bottle, 5.0g of 2- (4- (9H-carbazol-9-yl) phenoxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of dibenzoylphenyl phosphine oxide were added, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (five) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the thickness of 61 mu m; the film curing rate is 93.3%, the maximum ultraviolet absorption range reaches 350nm, and the light transmittance for 430-800 nm wavelength is 95.2%.
Example 6
In a brown glass bottle, 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 dibenzoyl phenyl phosphine oxide were added, and after stirring at room temperature for 2 hours in the absence of light, a photocurable composition glue (six) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the film thickness of 69 mu m; the film curing rate is 92.5%, the maximum ultraviolet absorption range reaches 378nm, and the light transmittance for 430-800 nm wavelength is 94.7%.
Example 7
In a brown glass bottle, 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 dibenzoylphenylphosphine oxide were added, and after stirring at room temperature for 2 hours under dark conditions, a photocurable composition glue (seventh) was obtained.
Then, the ink is coated on the surface of the substrate by the ink-jet printing objectBy 10mW/cm 2 Irradiating the substrate for 100s by an ultraviolet lamp to cure the substrate to form an organic packaging barrier film, wherein the thickness of the film is 76 mu m; the film curing rate is 91.9%, the maximum ultraviolet absorption range reaches 392nm, and the light transmittance for 430-800 nm wavelength is 93.3%.
Example 8
In this example, the acrylic monomer containing a large conjugated aromatic ring was 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate, and the synthetic route was as follows:
the preparation process is as follows:
26.2g of 2-bromodibenzo [ b, d ] thiophene, 6.2g of ethylene glycol, 27.6g of potassium carbonate and 1.0g of copper acetate are added into a reaction bottle under a nitrogen atmosphere, the reaction mixture is cooled to room temperature after being heated to 130 ℃ and stirred for 24 hours, and an organic layer is obtained by washing with water and extracting with dichloromethane;
the organic layer was dried over anhydrous sodium sulfate, concentrated to remove dichloromethane, 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;
next, the obtained 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethan-1-ol and 10.8g of methacryloyl chloride were dissolved in 200mL of dried pyridine, and after stirring at room temperature under nitrogen atmosphere for 24 hours, concentrated, and the residue was purified by a silica gel column to obtain 13.6g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethanamate in 63% yield.
In a brown glass bottle, 5.0g of 2- (dibenzo [ b, d ] thiophen-2-yloxy) ethyl methacrylate, 10.0g of glycerol diacrylate and 0.3g of dibenzoylphenyl phosphine oxide were charged, and after stirring at room temperature for 2 hours under light-shielding conditions, a photocurable composition glue (eight) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the film thickness of 73 mu m; the film curing rate is 93.9%, the maximum ultraviolet absorption range reaches 396nm,the transmittance at a wavelength of 430 to 800nm was 92.2%.
Example 9
Into a brown glass bottle, 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 dibenzoyl phenyl phosphine oxide were charged, and after stirring at room temperature in a dark place for 2 hours, a photocurable composition glue (nine) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the thickness of 80 mu m; the film curing rate is 91.8%, the maximum ultraviolet absorption range reaches 417nm, and the light transmittance for 430-800 nm wavelength is 91.3%.
Example 10
In a brown glass bottle, 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 dibenzoyl phenyl phosphine oxide were charged, and after stirring at room temperature in the absence of light for 2 hours, a photocurable composition glue (ten) was obtained.
Then, the substrate surface was coated with an ink jet print, followed by 10mW/cm 2 Irradiating the organic packaging barrier film for 100s to form an organic packaging barrier film with the thickness of 80 mu m; the film curing rate is 91.1%, the maximum ultraviolet absorption range reaches 428nm, and the light transmittance for 430-800 nm wavelength is 90.9%.
The optical performance evaluation method for the organic encapsulation barrier films formed in examples 1 to 10 described above was as follows:
photo-curing 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 -1 Absorption peak intensity near (c=o).
The photo-curing rate is as follows: photo-curing rate (%) = |1- (F/S) |x100; wherein F is 1635cm of the cured optical film with high refractive index -1 The intensity of the nearby absorption peak and the absorption peak at 1720cm -1 A ratio of nearby absorption peak intensities; s is 1635cm of the composition -1 Intensity of absorption peak in the vicinity andat 1720cm -1 The ratio of the intensities of the absorption peaks in the vicinity.
Transmittance: forming a sample from the composition by inkjet printing, followed by ultraviolet curing to form a photo-cured film; the transmittance of the cured film in the visible light range of 430 to 800nm was measured by an ultraviolet spectrophotometer.
In combination with the above evaluation mode, the photo-curing rate and the transmittance of the organic packaging barrier films formed by the photo-curing composition glue prepared in the embodiments 1 to 10 of the present invention are shown in the following table, wherein A represents an acrylic compound monomer containing a large conjugated aromatic ring, B represents a photo-curable monomer, and C represents a photo-crosslinking initiator.
According to the experimental data in the table, under the premise that the content of the acrylic compound monomer A containing the large conjugated aromatic ring is unchanged, the content of the photo-curable monomer B is increased, so that the photo-curing rate and the light transmittance of the glue can be enhanced; according to the above examples 1-10, in combination with the actual production requirements, the final preferred photocurable composition comprises the following glue components in parts by weight: 4 parts of acrylic compound monomer A containing large conjugated aromatic ring, 8 parts of photo-curable monomer B and 0.25 part of photo-crosslinking initiator C.
In conclusion, the photo-curing composition glue containing the large conjugated aromatic ring acrylic monomer provided by the invention can not only enhance the ultraviolet light absorption capacity of the monomer and promote the photo-curing crosslinking process, but also expand the ultraviolet light absorption range of the curing film and enhance the protection capacity of the curing film on a packaging object.
The above is only a specific content of the technical solution 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 will be understood that the 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 (6)
1. The photo-curing composition glue containing the large conjugated aromatic ring acrylic acid compound monomer is characterized in that the photo-curing composition glue has a curing rate of 91.0-97.2% and a light transmittance of 90-96.3% to 430-800 nm wavelength after being cured by ultraviolet light or blue light with the wavelength of 200-450 nm to form an organic film protective layer with the thickness of 25-80 mu m; the light-cured composition glue comprises the following components in parts by weight: 2 to 85 parts of large conjugated aromatic ring acrylic compound monomer, 2 to 85 parts of photo-curable monomer and 0.1 to 8 parts of photo-crosslinking initiator;
the structural general formula of the large conjugated aromatic ring acrylic acid compound monomer is as follows:
wherein the substituents R 1 Is hydrogen atom or alkyl chain with carbon chain length of 1-6; r is R 2 Is an alkyl chain with a carbon chain length of 1-6; r is R 3 Is a large conjugated aromatic ring; the large conjugated aromatic ring R 3 At least one derivative of phenanthrene, anthracene, pyrene, dibenzothiophene, dibenzofuran and carbazole compounds;
the large conjugated aromatic ring R 3 Comprises at least one structure in the following general formula:
the photo-crosslinking initiator is one or more of hydroxybenzophenone, benzoyl diphenyl phosphine oxide, dibenzoyl phenyl phosphine oxide, 4' -dichloro benzophenone acrylated benzophenone, 4' -bis (dimethylamino) benzophenone and 3,3' -dimethyl-2-methoxy benzophenone.
2. The glue of claim 1, wherein the photocurable monomer comprises at least one of the following: c (C) 1 To C 30 Monofunctional (meth) acrylic esters of monohydric alcohols, C 2 To C 30 Di (meth) acrylic esters of dihydric, trihydric, tetrahydric or pentahydric alcohols,
C 3 to C 30 Tri (meth) acrylic acid esters of triols, tetrols or pentaols.
3. A method for using the photo-curing composition glue containing a large conjugated aromatic ring acrylic compound monomer, which is characterized in that the photo-curing composition glue of any one of claims 1-2 is firstly adhered to the surface of an organic electronic device by adopting a spin coating, ink-jet printing, screen printing or knife coating method; and then irradiating the glue layer attached to the surface of the device by using light with the wavelength of 200-450 nm to solidify the glue layer, wherein the irradiation time is between 10 and 100 seconds, and finally forming the organic film with the thickness of 25-80 mu m.
4. The method of claim 3, wherein the organic film has a maximum absorption of 420nm and an optical curing rate of 91.3% -97.2%.
5. The method according to claim 3, wherein the organic thin film has a transmittance of 92.2% to 96.3% for light having a wavelength of 430 to 800 nm.
6. The use of the photo-curing composition glue containing the large conjugated aromatic ring acrylic acid compound monomer according to claim 1 in the waterproof and oxygen-blocking 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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| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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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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