CN116082888A - Photocurable inkjet ink composition, use method and application thereof - Google Patents
Photocurable inkjet ink composition, use method and application thereof Download PDFInfo
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- CN116082888A CN116082888A CN202310017263.2A CN202310017263A CN116082888A CN 116082888 A CN116082888 A CN 116082888A CN 202310017263 A CN202310017263 A CN 202310017263A CN 116082888 A CN116082888 A CN 116082888A
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- CN
- China
- Prior art keywords
- ink composition
- photocurable
- inkjet ink
- acrylate
- photoinitiator
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims description 12
- 239000000178 monomer Substances 0.000 claims abstract description 46
- 150000003254 radicals Chemical class 0.000 claims abstract description 28
- 125000002091 cationic group Chemical group 0.000 claims abstract description 18
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 10
- 239000012952 cationic photoinitiator Substances 0.000 claims description 9
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000007641 inkjet printing Methods 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- 239000012949 free radical photoinitiator Substances 0.000 claims description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- IGGZRGUPRFINQE-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxy-3-propoxypropyl) prop-2-enoate Chemical compound CCCOC(OC(=O)C=C)C(C)(C)COC(=O)C=C IGGZRGUPRFINQE-UHFFFAOYSA-N 0.000 claims description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- FEUIEHHLVZUGPB-UHFFFAOYSA-N oxolan-2-yl prop-2-enoate Chemical class C=CC(=O)OC1CCCO1 FEUIEHHLVZUGPB-UHFFFAOYSA-N 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002834 transmittance Methods 0.000 abstract description 10
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000000016 photochemical curing Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000004806 packaging method and process Methods 0.000 description 5
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- UYQMSQMCIYSXOW-UHFFFAOYSA-N benzene-1,2,4,5-tetrol Chemical compound OC1=CC(O)=C(O)C=C1O UYQMSQMCIYSXOW-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000012812 general test Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- -1 iron arene Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000005839 radical cations Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 2
- PZNYRERWHNMQFH-UHFFFAOYSA-N 3-(2-chloroethoxy)prop-1-ene Chemical group ClCCOCC=C PZNYRERWHNMQFH-UHFFFAOYSA-N 0.000 description 1
- LNGQLHZIYFQUIR-UHFFFAOYSA-N 3-chlorocyclohexene Chemical compound ClC1CCCC=C1 LNGQLHZIYFQUIR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
-
- 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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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Electromagnetism (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention relates to the technical field of photo-curable ink compositions, in particular to a photo-curable ink composition and application thereof. Comprises 10-80 percent of cationic photo-curable monomer, 15-75 percent of free radical photo-curable monomer and 1-10 percent of photoinitiator by weight percent. The photo-curable ink composition prepared by the invention has higher transmittance of visible light of 400-780 nm, higher adhesive force, lower curing shrinkage and excellent tensile strength and elongation at break.
Description
Technical Field
The invention belongs to the technical field of photo-curable ink compositions, and relates to a photo-curable ink-jet ink composition, a use method and application thereof.
Background
The photo-curable ink capable of being printed by ink jet can be coated on a substrate through an ink jet printer, can be cured in a short time by Ultraviolet (UV) light irradiation, is firmly attached to the surface of the substrate, and the cured film has excellent hydrophobic and solvent resistance, has no discharge of any organic matters (V0C is almost 0) in the curing process, thus avoiding the environmental protection problem of solvent type ink, and can be widely applied to packaging of flexible electronic devices. The cured films currently used to package flexible electronic devices are thin, and thus excellent leveling properties of the photocurable ink are required at the time of preparation.
In addition, the application amount of the photo-curable ink as the packaging material is continuously and rapidly developed, with the increase of the application amount, the photo-curable ink generally adopts a free radical photo-curing system due to the requirement of curing speed, and simultaneously a large amount of monomers are added to meet the requirement of low viscosity, and the free radical photo-curing system has the defects of high reaction activity, high photo-curing speed, serious oxygen inhibition, large curing shrinkage, high dielectric constant and the like. The cationic photo-curable system has the advantages of small viscosity, small curing shrinkage, easy generation of hydrogen bonds in reaction, strong adhesion to a substrate and the like, but the cationic curing system has the disadvantages of slower curing speed, poor flexibility, easy temperature and the like; the free radical-cation hybrid curing system has the advantages of both, has the advantages of short-term, fast curing, high curing rate and small shrinkage, has become the development trend of the UV curing field, and is increasingly applied to production practice.
Patent application CN 110894361A provides a photocurable packaging composition, a packaging structure and a semiconductor device, in which a photocurable silicon-containing monomer, a photocurable epoxy-containing alkyl diluent and a photoinitiator are used as main chains to form a cationic photocuring system, and the prepared polymer film has higher light transmittance, higher curing speed and lower plasma etching rate, but the photocurable packaging composition cannot be completely cured under the irradiation of ultraviolet light, dual curing of light and heat is required, and meanwhile, the cured polymer film has poor flexibility.
Patent application CN 114058198A provides a composition for encapsulating an OLED comprising a photocurable monomer, a silicon-containing monomer, and an initiator to form a free radical photocuring system, in which although the cured film has higher light transmittance and curing rate and excellent leveling and printing properties, the curing shrinkage rate is not less than 6, and still it is difficult to meet the requirements of encapsulation.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, and provides the following technical scheme:
a photo-curable ink-jet ink composition comprises, by weight, 10-80% of a cationic photo-curable monomer, 15-75% of a radical photo-curable monomer and 1-10% of a photoinitiator;
the structural general formula of the cationic photocurable monomer is shown as formula (1):
wherein m, n are each independently an integer of 1 to 6, R 1 ，R 4 Each independently is a photocurable group, which can be represented by formula (2) to formula (4):
wherein, represents binding position, A 1 、A 2 And A 3 Each independently is any one of hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy;
R 2 ，R 3 the structure of (2) is as shown in formula 5:
wherein W is an integer of 0 to 6;
X 1 ，X 2 ，X 3 ，X 4 ，X 5 ，X 6 ，X 7 each independently is substituted or unsubstituted C1.about.ultra-highAny of C6 straight chain or branched alkyl.
Further, the cationic photocurable monomer has the chemical formula shown in formulas (6) - (8):
further, the free radical photocurable monomer is one or a combination of several of monofunctional (meth) acrylate of C1 to C30 monohydric alcohol, di (meth) acrylate of C2-C30 monohydric alcohol or polyhydric alcohol, and tri (meth) acrylate of C3-C30 monohydric alcohol or polyhydric alcohol.
Further preferred, the free radical photocurable monomer is a mixture of monofunctional (meth) acrylates of C1 to C30 monohydric alcohols, di (meth) acrylates of C2 to C30 monohydric or polyhydric alcohols in a weight ratio of (1 to 20): 1.
further, the monofunctional (methyl) acrylate of the C1 to C30 monohydric alcohol is one or more of lauryl acrylate, butyl acrylate, hydroxyethyl acrylate, isobornyl acrylate, ethoxylated tetrahydrofuranyl acrylate and isobornyl methacrylate.
Further, the di (meth) acrylate of the C2-C30 monohydric alcohol or polyhydric alcohol is one or more of diethylene glycol diacrylate, triethylene glycol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, propoxyl neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate and 1, 4-butanediol diacrylate.
Further, the cationic photocurable monomer, the free radical photocurable monomer is (50-80) in weight ratio: (10-45).
Further, the photoinitiator is a mixture of a cationic photoinitiator and a free radical photoinitiator.
Further, the mass ratio of the cationic photoinitiator to the free radical photoinitiator is (1-6): (4-20).
Further, the free radical photoinitiator comprises at least one thioxanthone photoinitiator.
Further, the cationic photoinitiator is one or more combinations of iodonium salts, sulfonium salts, and iron arene.
In order to improve the storage property, application property and property of the cured film of the photocurable ink composition, it is preferable that the photocurable ink composition further comprises an auxiliary agent which is one or a mixture of more of silicone resin, fluorine-containing resin or polyacrylate leveling agent, silicone or organofluorine defoamer, heat stabilizer, photosensitizer, phosphorus-containing acrylate adhesion promoter, silicone surfactant wetting agent or polymerization inhibitor.
As the photocurable ink composition, in order to satisfy the process requirements of inkjet printing, it is preferable that the photocurable ink composition has a viscosity of 15 to 45 mPa.S at 25℃and a surface tension of 15 to 25mN/m.
The photocurable ink composition prepared according to the present invention can be printed by an inkjet printing technique without using a solvent, for which, on the one hand, the viscosity of the prepared ink may not be too high, otherwise the microscopic nozzles on the printhead may be clogged, and on the other hand, the surface tension may not be too low, otherwise the nozzles on the printhead may not escape and may not be formed into a spherical droplet shape, and, if the surface tension is too high, the ink may not be spread sufficiently on the substrate to form a thin layer.
A method for using the photo-curable ink-jet ink composition comprises the steps of coating the photo-curable ink-jet ink composition on the surface of a flexible electronic device to be packaged in an ink-jet printing mode, and then curing the photo-curable ink-jet ink composition by irradiation of ultraviolet light with wavelength of 395nm for 10-100 s to form a cured film with thickness of 5-15 mu m.
Use of a photocurable inkjet ink composition in an organic light emitting diode.
Compared with the prior art, the invention has the following beneficial effects:
1. according to the invention, the arrangement characteristics of the cured siloxane groups are regulated by limiting the relative positions of the siloxane groups and the photo-curable groups, so that excellent hydrophobic performance is realized, in addition, the siloxane groups have larger mobility and form larger two-dimensional molecular structures, so that the siloxane groups have lower water vapor and oxygen transmittance and visible light transmittance of 400-780 nm, and meanwhile, the leveling property of the photo-curable ink composition can be effectively improved by introducing the siloxane groups, so that the leveling uniformity of the film can be ensured when the film with the thickness of 5-15 mu m is prepared.
2. According to the invention, a free radical-cation hybrid curing system is formed through the synergistic effect of the cationic photo-curable monomer and the free radical photo-curable monomer, and an interpenetrating network structure is formed in the curing process by mixing the silicon-based vinyl and the acrylic ester system, so that the system complementation, the performance complementation and the cost complementation of the two systems are realized, the oxygen inhibition polymerization is effectively reduced, the curing shrinkage rate is reduced, the photo-curing rate and the adhesive force with a base material are improved, and meanwhile, the specific free radical photo-curable monomer is added, so that the viscosity and the surface tension of the photo-curable ink composition are effectively regulated, and the process requirement of inkjet printing is met.
3. The invention is characterized by limiting the weight ratio to (1-20): 1 and a C1 to C30 monohydric alcohol and a C2 to C30 monohydric or polyhydric alcohol, effectively improving the curing speed, thereby rapidly curing on the surface of a substrate to form a solid film layer, while both are not prone to excessive crosslinking at a specific ratio, so that the photocurable ink composition has excellent tensile strength and elongation at break after curing into a film, and can be applied to packaging organic light emitting diodes.
4. The photo-curable ink composition prepared by the invention has higher transmittance in the visible light range of 400-780 nm, higher curing rate, lower curing shrinkage and excellent flexibility. Other features of the present invention and its advantages will become apparent from the following detailed description of exemplary embodiments of the invention.
Detailed Description
Reference will now be made in detail to the exemplary embodiments, examples of which are not intended to represent all embodiments consistent with the invention. Rather, they are merely examples of devices that are consistent with aspects of the invention that are set forth in the following claims.
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.
Preparation example 1
The synthesis method of formula 6:
142.1g of 1,2,4, 5-tetrahydroxybenzene, 193.7g of ethylene carbonate and 13.8g of potassium carbonate are added into a reaction bottle, 400mL of DMF is added, the gas is replaced by argon for three times, 110 ℃ is used for reaction, TLC monitors the reaction until the raw materials are reacted, the reaction is cooled to room temperature, the system is added into 1000mL of water, the precipitate is filtered, washed by water for three times, and the intermediate 1-A is obtained after vacuum drying, and the yield is 93%.
230.2g of intermediate 1-A,256.5g of 3-chlorocyclohexene and 414.6g of potassium carbonate are added into a reaction bottle, 400mL of DMF is added, the gas is replaced by argon for three times, the reaction is carried out for 16h at 60 ℃, TLC monitors the reaction until the raw materials are reacted, after cooling to room temperature, the system is added into 1000mL of water, extraction is carried out for three times by ethyl acetate, the organic phases are combined and washed once, the organic phases are dried by sodium sulfate, the solvent is removed by reduced pressure distillation, and the intermediate 1-B is obtained by column chromatography separation, and the yield is 78%.
500mL of anhydrous THF is added into a reaction bottle, 390.5g of intermediate 1-B and 303.6g of triethylamine are added into a system, argon is used for replacing gas for three times, the temperature is reduced to 0 ℃, 322.7g of dimethyldichlorosilane is dropwise added through a constant pressure dropping funnel, the reaction time is about 4 hours after the dropwise addition, the reaction time can be increased to room temperature for 6 hours, TLC monitors that the reaction of the raw materials is completed, 303.6g of triethylamine is added, 225.5g of trimethylsilanol is dropwise added through the constant pressure dropping funnel after the dropwise addition is completed for about 2 hours, the reaction time is increased to reflux overnight, and the post treatment is carried out after the reaction of the raw materials is completed after the TLC monitors. The system was cooled to room temperature, then added into 1000mL of water, extracted three times with ethyl acetate, the organic phases were combined and washed once with water, the organic phases were dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the intermediate 1-C was isolated by column chromatography in 84% yield.
683.1g of intermediate 1-C,500mL of DCM, and the reaction flask were placed in a reaction vessel at 0deg.C; 517.7g of m-chloroperoxybenzoic acid (mCPBA) is dissolved in 300mL of DCM, a DCM solution of mCPBA is added into the system in a constant pressure dropping funnel in a dropwise manner, after the dropwise addition is completed, the temperature can be slowly raised to room temperature for continuous reaction for 18h, TLC monitors the reaction until the raw material reaction is completed, the system is added into 1000mL of water, DCM is extracted for three times, the organic phases are combined for water washing once, the organic phases are dried by sodium sulfate, the solvent is removed by reduced pressure distillation, and the target product 001 is obtained by column chromatography separation, and the yield is 95%.
Preparation example 2
The synthesis method of formula 7:
400mL of DMF was added to the reaction flask, 142.1g of 1,2,4, 5-tetrahydroxybenzene, 265.3g of 3- (2-chloroethoxy) propylene and 414.6g of potassium carbonate were added to the flask respectively, the gas was replaced with argon for three times, the reaction was carried out at 60℃for 16h, the TLC was monitored until the reaction of the raw materials was completed, the system was added to 1000mL of water after cooling to room temperature, extraction with ethyl acetate was carried out three times, the organic phase was combined and washed once with water, the organic phase was dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the intermediate 2-A was isolated by column chromatography in 63% yield.
500mL of anhydrous THF is added into a reaction bottle, 310.3g of intermediate 2-A and 303.6g of triethylamine are added into a system, argon is used for replacing gas for three times, the temperature is reduced to 0 ℃, 322.7g of dimethyldichlorosilane is dropwise added through a constant pressure dropping funnel, the reaction time is about 4 hours after the dropwise addition, the reaction time can be increased to room temperature for 6 hours, TLC monitors the reaction until the raw material reaction is completed, 303.6g of triethylamine is added, 225.5g of trimethylsilanol is dropwise added through the constant pressure dropping funnel after the dropwise addition is completed for about 2 hours, the reaction time is increased to reflux overnight, and the post treatment is carried out after the TLC monitors the reaction until the raw material reaction is completed. And cooling the system to room temperature, adding the system into 1000mL of water, extracting with ethyl acetate for three times, combining the organic phases, washing the organic phases once with water, drying the organic phases with sodium sulfate, distilling under reduced pressure to remove the solvent, and separating by column chromatography to obtain the target product of the formula 002, wherein the yield is 84%.
Preparation example 3
The synthesis method of formula 8:
603.1g of the compound of formula 7, 500mL of DCM, and the system placed at 0deg.C; 517.7g of m-chloroperoxybenzoic acid (mCPBA) is dissolved in 300mL of DCM, a DCM solution of mCPBA is added into the system by a constant pressure dropping funnel, after the dropwise addition is completed, the temperature can be slowly raised to room temperature for continuous reaction for 18h, TLC monitors the reaction until the raw material reaction is completed, the system is added into 1000mL of water, DCM is extracted for three times, the organic phases are combined for water washing once, the organic phases are dried by sodium sulfate, the solvent is removed by reduced pressure distillation, and the target product of formula 8 is obtained by column chromatography separation, and the yield is 92%.
Example 1: preparation of the photocurable inkjet ink composition 1 of this example
The components used are described below:
(A) Cationic photocurable monomer: (A1) a monomer comprising formula 6;
(B) Free radical photocurable monomer: (B1) Lauryl acrylate (TCI), (B2) triethylene glycol diacrylate (TCI);
(C) Radical photoinitiator: isopropyl Thioxanthone (ITX) (strong force, constant state);
(D) Cationic photoinitiator: irgacure-261 (BASF Basff).
Adding 50% (A1), 33% (B1), 10% (B2), 5% (C) and 2% (D) of the total mass into a brown glass bottle, stirring and mixing for 3h at room temperature, and filtering to obtain a photocurable inkjet ink composition 1; and then ultraviolet light curing the photo-curable inkjet ink composition 1 to obtain a cured film.
Example 2: preparation of the photocurable inkjet ink composition 2 of this example
The components used are described below:
(A) Cationic photocurable monomer: (A2) a monomer comprising formula 7;
(B) Free radical photocurable monomer: (B1) Lauryl acrylate (TCI), (B2) triethylene glycol diacrylate (TCI);
(C) Radical photoinitiator: isopropyl Thioxanthone (ITX) (strong force, constant state);
(D) Cationic photoinitiator: irgacure-261 (BASF Basff).
Adding 60% (A2), 28% (B1), 5% (B2), 5% (C) and 2% (D) of the total mass into a brown glass bottle, stirring and mixing for 3h at room temperature, and filtering to obtain a photocurable inkjet ink composition 2; and then ultraviolet curing the photo-curable inkjet ink composition 2 to obtain a cured film.
Example 3: preparation of the photocurable inkjet ink composition 3 of this example
The components used are described below:
(A) Cationic photocurable monomer: (A3) a monomer comprising formula 8;
(B) Free radical photocurable monomer: (B1) Lauryl acrylate (TCI), (B2) triethylene glycol diacrylate (TCI);
(C) Radical photoinitiator: isopropyl Thioxanthone (ITX) (strong force, constant state);
(D) Cationic photoinitiator: irgacure-261 (BASF Basff).
Adding 75% (A3), 15% (B1), 3% (B2), 5% (C) and 2% (D) of the total mass into a brown glass bottle, stirring and mixing for 3 hours at room temperature, and filtering to obtain a photocurable inkjet ink composition 3; and then ultraviolet curing the photo-curable inkjet ink composition 3 to obtain a cured film.
Example 4: preparation of the photocurable inkjet ink composition 4 of this example
The components used are described below:
(A) Cationic photocurable monomer: (A1) a monomer containing formula 6, (A2) a monomer containing formula 7;
(B) Free radical photocurable monomer: (B1) Lauryl acrylate (TCI), (B2) triethylene glycol diacrylate (TCI);
(C) Radical photoinitiator: isopropyl Thioxanthone (ITX) (strong force, constant state);
(D) Cationic photoinitiator: irgacure-261 (BASF Basff).
Adding 40% (A1), 30% (A2), 18% (B1), 5% (B2), 5% (C) and 2% (D) of the total mass into a brown glass bottle, stirring and mixing for 3h at room temperature, and filtering to obtain a photocurable inkjet ink composition 4; and then ultraviolet light curing the photo-curable inkjet ink composition 4 to obtain a cured film.
Comparative example 1:
comparative example 1 is different from example 1 in that a radical photo-curable monomer is not added to comparative example 1, and an epoxy-based photo-curable monomer, specifically polyethylene glycol diglycidyl ether, is added to comparative example 1.
Comparative example 2:
comparative example 2 differs from example 1 in that in comparative example 2, no A1 was added, A2 was added, and only lauryl acrylate (TCI) was added as the radical photo-curable monomer.
Comparative example 3:
comparative example 3 differs from example 1 in that in comparative example 3, no A1 was added, A2 was added, and only triethylene glycol diacrylate (TCI) was added to the radical photo-curable monomer.
Detailed information of the components used in examples and comparative examples is shown below.
(A) Cationic photocurable monomer: a is that 1 Is of formula 6; a is that 2 Is of formula 7; a is that 3 Is formula 8.
(B) Free radical photocurable monomer: b1 is lauryl acrylate (TCI); b2 is triethylene glycol diacrylate (TCI).
(C) Radical photoinitiator: isopropyl Thioxanthone (ITX) (strong force in everstate).
(D) Cationic photoinitiator: irgacure-261 (BASF Basff).
(E) Epoxy-based photocurable monomer: polyethylene glycol diglycidyl ether (PEG 400) (Jiangsu Sanmu).
Table 1 compares the performance tests of examples and comparative examples, raw materials were placed in a reactor, stirred and mixed at room temperature for 3 hours, thereby obtaining a photocurable ink composition, and uv photocuring was performed to obtain a cured film, and the obtained cured film was subjected to the performance test, and the specific test method is as follows:
(1) Cure shrinkage: inkjet printing of a photocurable ink composition on a glass substrate and at 30mW/cm 2 It was subjected to UV curing by UV irradiation to produce a specimen having dimensions of 5mm×3cm×1mm (width×length×thickness).
Cure shrinkage η= (Vb-Va)/vb×100%;
where Vb is the volume before curing and Va is the volume after curing.
(2) Tensile strength: the measurement is carried out according to GB/T1040-92 general test method for Plastic mechanical Properties (stretching). Instrument: WDW-5A microcomputer controlled electronic universal tester; test conditions: the stretching speed was 1mm/min, at least 5 samples per group, and the test results were averaged.
(3) Elongation at break: according to GB/T1040-92 general test method (stretching) for mechanical properties of plastics; test conditions: the stretching speed was 1mm/min, at least 5 samples per group, and the test results were averaged. The sample size was a dumbbell bar with a gauge length of 50mm and a thickness of 10 μm.
(4) Transmittance: the photocurable ink composition was cured by ultraviolet light to produce a sample having a size of 3cm×7.5cm×10 μm (width×length×thickness), and then the transmittance of the cured film in the 680nm visible light range was measured by an ultraviolet spectrophotometer (Fluoromax-4, france HORIBA Jobin Yvon).
Table 1.
As can be seen from table 1, the photocurable ink composition has a higher transmittance of visible light of 400 to 780nm, a higher curing rate, a lower curing shrinkage and excellent tensile strength and elongation at break.
In contrast, when the free radical photo-curable monomer was not added in comparative example 1, the addition of the epoxy-based photo-curable monomer was changed, so that the photo-curable ink composition was a cationic photo-curing system, the curing time was greatly increased, the curing rate was lowered, and the flexibility was deteriorated (elongation at break was lower). The radical photo-curable monomer described in comparative example 2 was lauryl acrylate (mono-functional (meth) acrylate), triethylene glycol diacrylate (B2) was not added, and the cured film prepared was increased in flexibility (elongation at break up to 15.6%), but poor in strength (tensile strength of only 17.4%), and also increased in cure shrinkage; in comparative example 3, the radical photo-curable monomer was triethylene glycol diacrylate (di (meth) acrylate), and lauryl acrylate (mono-functional (meth) acrylate) was not added, and the system was excessively crosslinked, so that the prepared cured film was low in light transmittance, high in curing shrinkage, and poor in flexibility, and the elongation at break was only 3.6%.
The foregoing is only a specific embodiment of the invention to enable those skilled in the art to understand or practice the 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 (9)
1. A photocurable inkjet ink composition, characterized by comprising, by weight, 10-80% of a cationic photocurable monomer, 15-75% of a radical photocurable monomer and 1-10% of a photoinitiator;
the structural general formula of the cationic photocurable monomer is shown as formula (1):
wherein m, n are each independently an integer of 1 to 6, R 1 ，R 4 Each independently is a photocurable group, which can be represented by formula (2) to formula (4):
wherein, represents binding position, A 1 、A 2 And A 3 Each independently is any one of hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C1 to C20 alkoxy;
R 2 ，R 3 the structure of (2) is as shown in formula 5:
wherein W is an integer of 0 to 6;
X 1 ，X 2 ，X 3 ，X 4 ，X 5 ，X 6 ，X 7 each independently is any one of a substituted or unsubstituted C1-C6 linear or branched alkyl group.
2. The photocurable inkjet ink composition of claim 1, wherein the cationic photocurable monomer has the formula (6) - (8):
3. the photocurable inkjet ink composition of claim 1, wherein the free radical photocurable monomer is one or a combination of monofunctional (meth) acrylates of C1-C30 monohydric alcohols, di (meth) acrylates of C2-C30 monohydric or polyhydric alcohols, and tri (meth) acrylates of C3-C30 monohydric or polyhydric alcohols.
4. A photocurable inkjet ink composition according to claim 3 wherein the monofunctional (meth) acrylate of C1 to C30 monohydric alcohol is one or more of lauryl acrylate, butyl acrylate, hydroxyethyl acrylate, isobornyl acrylate, ethoxylated tetrahydrofuranyl acrylate, isobornyl methacrylate.
5. A photocurable inkjet ink composition according to claim 3 wherein the di (meth) acrylate of a C2-C30 monohydric or polyhydric alcohol is one or more of diethylene glycol diacrylate, triethylene glycol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, propoxyl neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, 1, 4-butanediol diacrylate.
6. A photocurable inkjet ink composition according to claim 1 wherein the photoinitiator is a mixture of a cationic photoinitiator and a free radical photoinitiator.
7. A photocurable inkjet ink composition according to claim 6 wherein the free radical photoinitiator comprises at least one thioxanthone photoinitiator.
8. The method of using a photocurable inkjet ink composition according to any one of claims 1-7 wherein the photocurable inkjet ink composition is applied to the surface of the flexible electronic device to be encapsulated by means of inkjet printing and then cured by irradiation with ultraviolet light having a wavelength of 395nm for 10-100 s to form a cured film having a thickness of 5-15 μm.
9. Use of a photocurable inkjet ink composition according to any one of claims 1 to 7 wherein the photocurable ink composition is used in the protection of organic light emitting diode packages.
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| CN113773699A (en) * | 2021-11-08 | 2021-12-10 | 西安思摩威新材料有限公司 | Ultraviolet curing packaging ink based on two-dimensional epoxy monomer containing silicon-oxygen side chain, use method and application thereof |
| CN115491131A (en) * | 2022-10-26 | 2022-12-20 | 西安思摩威新材料有限公司 | Ultraviolet curing organic glue for OLED packaging and use method thereof |
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