WO2021256814A1 - Composition d'encapsulation et diode électroluminescente - Google Patents

Composition d'encapsulation et diode électroluminescente Download PDF

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Publication number
WO2021256814A1
WO2021256814A1 PCT/KR2021/007436 KR2021007436W WO2021256814A1 WO 2021256814 A1 WO2021256814 A1 WO 2021256814A1 KR 2021007436 W KR2021007436 W KR 2021007436W WO 2021256814 A1 WO2021256814 A1 WO 2021256814A1
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Prior art keywords
monomer
group
composition
encapsulant composition
dielectric constant
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PCT/KR2021/007436
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English (en)
Korean (ko)
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이주영
김경종
Original Assignee
코오롱인더스트리 주식회사
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Priority to CN202180024714.4A priority Critical patent/CN115335470B/zh
Publication of WO2021256814A1 publication Critical patent/WO2021256814A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
    • 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

Definitions

  • the present invention relates to an encapsulant composition, and more particularly, to an encapsulant composition, an organic cured film formed from the encapsulant composition, a laminate including the organic cured film, and a light emitting device.
  • a light emitting device particularly an organic light emitting device (OLED) is a self-luminous device used in TVs, computers, mobile communication devices, etc. , it has excellent driving voltage and response speed characteristics and has the advantage of being able to be multicolored, so it is widely used in a wide variety of fields.
  • OLED organic light emitting device
  • the organic light emitting device when the organic light emitting device is exposed to oxygen, moisture, and ultraviolet rays, there is a problem in that physical properties and lifespan are reduced due to deterioration.
  • a sealing means in which an organic layer having barrier properties against gas and moisture and an inorganic layer having excellent mechanical properties are alternately stacked is being considered.
  • the inorganic layer may be formed through a deposition method, and the organic layer may be formed using inkjet printing.
  • Embodiments of the present invention for solving the above problems confirm that the photocurable monomers show incompatible characteristics between curability and dielectric constant, and provide a composition optimized for improving curability and dielectric constant, so that even if external static electricity is introduced into the light emitting device, electrical
  • An object of the present invention is to provide an encapsulant composition capable of solving a driving defect problem by not interfering with a signal and preventing capacitance disturbance, and a light emitting device including the same.
  • a first monomer group a second monomer group; and an initiator
  • the first monomer group includes at least one first monomer compound
  • the first monomer compound has an acryl end group and includes an ethylenically unsaturated hydrocarbon compound represented by the following formula 2
  • the second monomer group includes two or more second monomer compounds, the second monomer compound has an acryl end group, includes an ethylenically unsaturated hydrocarbon compound represented by the following formula 3
  • the first monomer The group has a first dielectric constant of 2.90 to 4.45
  • the second monomer group has a second dielectric constant of 4.46 to 8.20.
  • a is an integer of 15 to 28
  • b is an integer of 28 to 54
  • c is an integer of 1 to 4
  • Equation 3 d is an integer of 10 to 25
  • e is an integer of 10 to 40
  • f is an integer of 1 to 9
  • the two or more second monomer compounds may include one or more aromatic second monomer compounds and one or more aliphatic second monomer compounds.
  • the first monomer group may be included in an amount of 40 to 80 wt%
  • the second monomer group may be included in an amount of 20 to 60 wt%
  • the ratio ([C] / [ O]) may be greater than or equal to 7.5.
  • At least one of the one or more first monomer compounds and the two or more second monomer compounds may be liquid.
  • the encapsulant composition may have a liquid dielectric constant of 4.20 or less at 25 degrees Celsius.
  • the encapsulant composition may have a solid-state dielectric constant of 2.70 or less upon curing.
  • the encapsulant composition may have a viscosity of 1 to 20 cPs at 25 degrees Celsius.
  • the encapsulant composition may be a solvent-free type.
  • a light emitting device having at least one surface of the organic cured film of the encapsulant composition described above.
  • the encapsulant composition according to the embodiments of the present invention exhibits a low dielectric constant, so that when the dielectric thin film and high resolution are made, external static electricity is introduced into the substrate to interfere with the electrical signal, thereby solving the problem of affecting the driving.
  • the encapsulant composition according to embodiments of the present invention exhibits a low dielectric constant, so that capacitance disturbance can be prevented.
  • the encapsulant composition according to the embodiments of the present invention has a low dielectric constant and has a curing characteristic known to be incompatible with the dielectric constant, and provides improved storage stability and jetting spreadability so that it can be used in the inkjet process as well as There is an effect of improving the reliability stability and lifespan characteristics of the physical properties of the light emitting device.
  • the encapsulant composition according to embodiments of the present invention has an effect of providing the properties of the encapsulant without additionally forming an encapsulant film.
  • the present invention relates to an encapsulant composition that can be printed on a substrate and can be photocured.
  • the encapsulant composition relates to an organic composition capable of forming an organic layer of the encapsulant.
  • printing may refer to various coatings including printing and inkjetting.
  • the encapsulant including the cured product of the organic composition may be positioned on the organic light emitting device to inhibit or prevent the organic layer of the organic light emitting device from being damaged from physical impact or from being damaged from external penetrating materials such as oxygen or moisture.
  • composition for an organic cured film of the encapsulant of the present invention is configured to effectively prevent the inflow of static electricity, which is an electrical signal interference element, as well as a light emitting device protection function inherent to the encapsulant.
  • the encapsulant composition may be a solvent-free photocurable composition. That is, the composition used to form an organic cured film for an encapsulant, which will be described later, may be a composition that is non-solvent and includes a photocurable component.
  • solvent-free composition means that the composition does not contain a solvent, for example, an organic solvent or an aqueous solvent.
  • the term “photocurable composition” refers to a composition that can be cured by radical polymerization according to light irradiation.
  • the photocuring may be performed, for example, by irradiation with electromagnetic waves such as microwaves, infrared rays, ultraviolet rays, and gamma rays, or particle beams such as electron beams such as alpha-particle beams, proton beams, and Neutron beams.
  • Specific photocuring conditions are not particularly limited, but, for example, when photocuring is performed by ultraviolet rays, the wavelength may be in a range including 290 to 400 nm, which is a near ultraviolet region, and the intensity of light during the total time of irradiation with ultraviolet rays is 400 mW/cm 2 or less, or in the range of 100 to 400 mW/cm 2 , and the amount of light may be in the range of 300 to 2500 mJ/cm 2 , or 500 to 1500 mJ/cm 2 .
  • the solvent drying process can be omitted, thereby improving process efficiency, and solving the disadvantages of the generation of bubbles due to the solvent and the deterioration of the function of the encapsulant.
  • the solvent-free composition can reduce its own moisture content in the encapsulant composition, and thus has an advantage suitable for an organic light emitting device that is vulnerable to moisture.
  • the composition may be a composition applied on a substrate by inkjet printing.
  • inkjet printing is advantageous in mass production and the like because it uses a multi-head connecting several nozzles.
  • the composition is configured to satisfy the viscosity and surface energy (tension) described below to be applicable to inkjet printing.
  • the composition may include a compound having a photocurable functional group.
  • the composition may be provided as a composition in which the dielectric constant is lowered by combining the first monomer group and the second monomer group.
  • permittivity refers to liquid permittivity unless otherwise specified. A specific measurement method is disclosed in Experimental Examples to be described later.
  • a low polarity monomer In order to lower the dielectric constant, a low polarity monomer must be used. Even for a low polarity monomer, in the case of a monomer having a low dielectric constant, there is often only one functional group that generates radicals during photocuring, so that a cured film is not formed even after photocuring. , permittivity and curing characteristics are incompatible with each other.
  • a monomer capable of compensating for insufficient curing characteristics for example, a monomer that has a high dielectric constant but has sufficient functional groups that generate radicals during photocuring and can form a desired cured film during photocuring is used in combination to increase the dielectric constant by 10% or more compared to the prior art
  • a monomer that has a high dielectric constant but has sufficient functional groups that generate radicals during photocuring and can form a desired cured film during photocuring is used in combination to increase the dielectric constant by 10% or more compared to the prior art
  • C the dielectric constant measured in the encapsulant composition containing the first and second monomer groups, and 1,14-tetradecane dimethacrylate, which is known in the industry as the conventional encapsulant composition, was used.
  • the correlation between C and D calculated by the following formula is 10 or more, 12 or more, 12 to 20, 20 to 30, or 12 to 18 can be Within the above range, it is preferable to overcome the incompatible characteristics between the above-described curing characteristics and dielectric constant, and provide improved curing performance and significantly reduced dielectric constant at the same time.
  • the calculated value of Equation 1 is 10 or more
  • the dielectric constant is improved by 10% or more compared to the aforementioned reference value (D, 4.56), and in this case, it can be interpreted that curing characteristics are also secured.
  • the encapsulant composition according to an embodiment of the present invention includes an initiator in a first monomer group having a first dielectric constant and a second monomer group having a second dielectric constant.
  • the first monomer group includes one or more first monomer compounds
  • the second monomer group includes two or more second monomer compounds.
  • the first monomer compound and the second monomer compound may each independently have a (meth)acrylate group or a vinyl group as a photocurable functional group.
  • a monomer which has a (meth)acrylate group the monofunctional (meth)acrylate of a monoalcohol or polyhydric alcohol, or the polyfunctional (meth)acrylate of a monoalcohol or polyhydric alcohol is mentioned, for example.
  • a monomer which has a vinyl group the aromatic compound containing vinyl groups, such as styrene and vinyl toluene, is mentioned.
  • the composition may include two or more of the compounds listed above.
  • the first monomer compound may be a monofunctional polymerizable monomer, a polyfunctional polymerizable monomer, or an oligomer thereof.
  • the first monomer compound may be a monofunctional polymerizable monomer having a condensed cyclic hydrocarbon group or a polycyclic hydrocarbon group.
  • the type of the specific compound is not particularly limited as long as the first monomer compound includes an ethylenically unsaturated hydrocarbon compound having a general formula represented by Formula 2 below.
  • Equation 2 a may be an integer of 15 to 28.
  • a is an integer of 16-28.
  • Equation 2 b may be an integer of 28 to 54.
  • b is an integer of 30-54.
  • Equation 2 c may be an integer of 1 to 4.
  • c is an integer of 2-4.
  • the first monomer compound is, as a specific example, 2-decyl-1-tetradecane (meth) acrylate, stearyl (meth) acrylate, 2-octyl-dodecyl (meth) acrylate, 2-hexyl-decyl ( Meth) acrylate, iso-stearyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate and the like can be used.
  • the first monomer compound may have any one of structures represented by the following Chemical Formulas 1-1, 1-2, 1-3, 1-4, and 1-5.
  • n is preferably 5 or more, in Formula 1-2, n is preferably 5 or more, In Formula 1-3, n is preferably 5 or more, and in Formula 1-4 In , n is preferably 5 or more, and in Formula 1-5, n is preferably 5 or more.
  • the first monomer compound may have any one of structures represented by the following Chemical Formulas 2-1 to 2-8.
  • the first monomer group may include two or more kinds of first monomer compounds.
  • the content of the first monomer group is 40 to 80 wt%, 50 to 80 wt%, 50 to 70 wt%, or 55 to 70wt May be within range tomorrow.
  • the first monomer group is 40 to 80 wt% based on 100 wt% of the encapsulant composition, even if external static electricity is introduced into the thin film and high resolution light emitting device, a driving defect does not occur.
  • the first monomer group includes one or more first monomer compounds, and the dielectric constant (first dielectric constant) of the first monomer group is 2.90-4.45, preferably 3.00-3.75.
  • the first dielectric constant is 2.90 to 4.45, it is preferable because it is possible to provide jetting spreadability and solid-phase transmittance while reducing the dielectric constant measured in the composition by 10% or more compared to the prior art while solving the problem of compatibility of curing and dielectric constant.
  • the first dielectric constant is a dielectric constant of a first monomer group including one or more first monomer compounds, and is a dielectric constant of a mixture obtained by mixing one or more first monomer compounds.
  • the second monomer compound may include at least one ethylenically unsaturated hydrocarbon compound having a general formula represented by the following formula 3, and specific types of compounds are not particularly limited.
  • d may be an integer of 10 to 25.
  • d is an integer of 10-22.
  • Equation 3 e may be an integer of 10 to 40.
  • e is an integer of 10-38.
  • f may be an integer of 1 to 9.
  • f is an integer of 2-4.
  • the second monomer compound may be a monofunctional polymerizable monomer, a polyfunctional polymerizable monomer, or an oligomer thereof.
  • the second monomer compound may be a polyfunctional polymerizable monomer having two or more functional groups. More preferably, the second monomer compound may be a polyfunctional polymerizable monomer having three functional groups, and the functional group may be any one of acrylate and methacrylate.
  • the second monomer compound may be a monofunctional polymerizable monomer having a condensed cyclic hydrocarbon group or a polycyclic hydrocarbon group.
  • the second monomer compound may be an aliphatic polymerizable monomer or an aromatic polymerizable monomer.
  • the second monomer compound may have any one of the structures represented by Chemical Formulas 3 and 4 below.
  • n is preferably 12 or more.
  • the structure represented by Chemical Formula 3 may be any one of the structures represented by Chemical Formulas 3-1 and 3-2 below.
  • the structure represented by Chemical Formula 3 is an aliphatic polymerizable monomer structure, and is referred to as an aliphatic second monomer compound in the present specification.
  • the structure represented by Chemical Formula 4 is an aromatic polymerizable monomer structure, and is referred to as an aromatic second monomer compound in the present specification.
  • the second monomer group includes two or more second monomer compounds, and the two or more second monomer compounds include one or more aromatic second monomer compounds and one or more aliphatic second monomer compounds. It may contain a monomer compound.
  • the aliphatic second monomer compound is a multifunctional monomer having two or more photocurable functional groups.
  • the surface layer of the encapsulant composition reduces radical generation under the influence of oxygen in the air. A phenomenon in which the polymerization rate is slowed may occur.
  • the ratio of the surface to the inside of the film increases, which may further cause a problem of lowering the polymerization rate according to the above phenomenon.
  • a curing speed can be secured faster, so the curing time can be shortened, and thus it can be advantageous in securing the physical properties required for an organic cured film for encapsulants.
  • the aromatic second monomer compound has an effect of improving the film strength and lowering the etch rate for plasma.
  • plasma treatment is performed to deposit the inorganic layer.
  • the content of the second monomer group may be in the range of 20 to 60 wt%, 30 to 50 wt%, 20 to 40 wt%, or 30 to 45 wt% based on 100 wt% of the total weight of the first and second monomer groups.
  • the second monomer group is 20 to 60 wt% with respect to 100 wt% of the encapsulant composition, even if external static electricity is introduced by the thin film and high-resolution light emitting device, driving failure does not occur, and the preferred viscosity range for use as the encapsulant composition is The range of 15-20 cPs can be satisfied.
  • the content of the at least one aromatic second monomer compound includes the first monomer group and
  • the content of the aliphatic second monomer compound may be 19 to 59 wt% based on 100 wt% of the total of the second monomer group and 100 wt% of the second monomer group. have.
  • the second monomer compound is, as specific examples, pentaerythritol di(meth)acrylate, dipentaerythritol di(meth)acrylate, 1,12-dodecanediol dimethacrylate, 1,14-tetradecene dimethacrylic Late, trimethylolpropane trimethacrylate, ortho-phenyl phenoxyl ethyl acrylate, etc. may be used.
  • the second monomer group includes two or more kinds of second monomer compounds, and the dielectric constant (second dielectric constant) of the second monomer group is 4.46 to 8.20, preferably 4.46 to 5.35.
  • the second dielectric constant is 4.46 to 8.20, it is preferable to solve the problem of compatibility of curing and dielectric constant, to lower the dielectric constant by 10% or more compared to the prior art, and to provide jetting spreadability and solid-phase transmittance together.
  • the second permittivity is a permittivity of a second monomer group including two or more kinds of second monomer compounds, and is a dielectric constant of a mixture obtained by mixing two or more kinds of second monomer compounds.
  • the at least one first monomer compound; and the at least two second monomer compounds; At least one of the mono-mo compounds may be in a liquid phase.
  • the ratio of the total number of carbons ([C]) to the total number of oxygens ([O]) calculated from carbon and oxygen of the first monomer group and carbon and oxygen of the second monomer group ( [C]/[O]) may be greater than or equal to 7.5.
  • [C]/[O] may be 8 or more.
  • [C] is the number of carbons
  • [O] is the number of oxygens.
  • the upper limit of [C]/[O] is not limited thereto, but may be 12.0 or less, preferably 11.5 or less.
  • the first monomer compound is an ethylenically unsaturated hydrocarbon compound having a structure of C27H52O2
  • the second monomer compound includes an ethylenically unsaturated hydrocarbon compound having a structure of C22H38O4 and an ethylenically unsaturated hydrocarbon compound having a structure of C17H16O3
  • the ratio of the total number of carbons to the total number of oxygens (C/ O) is 10.9, which satisfies 7.5 or more.
  • the initiator may provide radicals for photocuring the first monomer group and the second monomer group by absorbing light energy from the outside to the acryl end group of each monomer.
  • the initiator may be, for example, a material containing a hetero atom in the molecule and a backbone providing a radical and a material connected to the backbone by a carbonyl linking group and including at least one aryl end group.
  • a may be an integer of 3 or more.
  • the initiator may have a skeletal structure represented by any one of the following Chemical Formulas 5-1 and 5-2.
  • the terminal structure connected to the above-mentioned backbone structure by a carbonyl linking group may have, for example, Chemical Formula 6 below.
  • the initiator may improve the photocuring effect by using a material having an absorption wavelength in the range of 500 nm or less, or 380 to 410 nm.
  • hydroxy ketone series such as 1-hydroxy cyclohexylphenyl ketone (1-hydroxy cyclohexylphenyl ketone, Irgacure 184), 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl) Aminoketone series such as phenyl]-1-butanone, Irgacure 369) and alpha-aminoacetophenone (Irgacure 907), benzyldimethylketal series such as benzyldimethylketal (Irgacure-651), phenylbis(2,4,6) ,-trimethylbenzoyl) (Irgacure 819), such as bis-acyl phosphine series, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO), such as mono-acyl phosphine (mono) -acyl phosphine) series compounds can be used.
  • additives selected from the group consisting of heat stabilizers, UV stabilizers and antioxidants may be included, and various other types of additives may be used.
  • the initiator may be 5 parts by weight or less, 1 to 5 parts by weight, or 3 to 5 parts by weight, based on 100 parts by weight of the total monomer(s) constituting the encapsulant composition, and may be external to the encapsulant composition within the above range.
  • light energy is introduced from the first monomer compound of the first monomer group and the second monomer compound of the second monomer group constituting the encapsulant composition, it is suitable to supply radicals suitable for forming a coating film to the acrylic terminal groups, respectively. do.
  • the light energy may be, for example, provided from a laser or plasma having an intensity of 400 mW/cm 2 or less, 100 to 400 mW/cm 2 or 200 to 400 mW/cm 2 , but is not limited thereto.
  • a surfactant within a range that does not adversely affect the encapsulant composition, a surfactant, an adhesion aid for strengthening adhesion to the substrate, a stabilizer, an adhesion promoter, a curing accelerator, a thermal polymerization inhibitor, a dispersant, a plasticizer, a filler , an antifoaming agent, and the like.
  • additives may be used in an amount of 0.001 to 10% by weight based on the total weight of the encapsulant composition. In this case, when it is out of the above range, permeability, heat resistance, adhesion to the inorganic barrier layer, jetting stability, etc. of the cured film may be poor.
  • the surfactant can improve applicability, defoaming property, leveling property, etc., Florad FC-170C, Florad FC-430, Florad FC-431, Saffron S-112, Saffron S-113, Saffron S-131, Saffron S-141, Saffron S-145, SH- and fluorine-based surfactants such as 28PA, SH-190, SH-193, SZ-6032, and SF-8428.
  • the silane coupling agent which has reactive substituents such as a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group
  • attachment adjuvant is mentioned as an adhesion
  • trimethoxysilylbenzoic acid, ⁇ -methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ - (3,4- Epoxycyclohexyl) ethyl trimethoxysilane etc. are mentioned.
  • the composition may not include a silicone-derived unit.
  • a siloxane-based outgas may be generated under high-temperature conditions, which may damage the light emitting device.
  • the composition may have a moisture content of 20 ppm or less before curing. Since conventional light emitting devices are vulnerable to moisture, if necessary, the moisture content before curing can be adjusted to 20 ppm or less through a moisture removal process.
  • the composition has a viscosity suitable for the inkjet process, for example, a viscosity of 20 cPs or less, 1-20 cPs, or 15-20 cPs as measured by a Brookfield viscometer at 25 degrees Celsius, to improve both printing performance and curing performance It is preferable to be able to For reference, if the viscosity is too high, it is difficult to discharge from the inkjet nozzle, and if the viscosity is too low, flowability increases and it is difficult to form a coating film of an appropriate thickness.
  • the composition may have a surface energy (tension) within a range of 20 to 45 mN/m to facilitate ejection from the inkjet head. It is preferable to provide ink properties that can be smoothly ejected from the inkjet equipment within the above range. For reference, if the surface energy of the ink is large, ink droplets may scatter, and if the surface energy is low, the spreadability or dispersibility of the solution may increase when it collides with the substrate.
  • the measurement of the surface energy (tension) can be measured by various known methods, for example, it can be measured by the Ring Method at 25 degrees.
  • the encapsulant composition according to an embodiment may have a liquid dielectric constant of 4.20 or less measured at 25 degrees Celsius. Under the above conditions, the encapsulant composition having a liquid dielectric constant of 4.20 or less does not cause a driving defect in the light emitting device even if external static electricity flows into the coating film, and can effectively protect the coating film from oxygen, moisture, and ultraviolet rays even without an additional encapsulant.
  • the liquid dielectric constant of the conventionally mass-produced composition is in the range of about 4.50 or more and 6.20 or less, which is not suitable for generating parasitic capacitance between electrodes or preventing capacitance disturbance sufficiently.
  • the encapsulant composition formed of the above configuration may have a dielectric constant of 4.20 or less, 2.90 to 4.45, or 3.00 to 3.75.
  • the lower limit is not particularly limited because lowering the dielectric constant is advantageous in preventing capacitance disturbance.
  • the encapsulant composition according to one embodiment has a curing characteristic of 95% or more measured at 1000 mJ under a wavelength of 395 nm and an N2 atmosphere because it is possible to effectively produce a coating film with improved physical properties of the light emitting device.
  • the encapsulant composition provided according to an aspect of the present invention has an optical characteristic of 95% or more measured using a UV-Vis spectrometer, since it is possible to improve the light emitting characteristic together with the physical properties of the light emitting device.
  • the encapsulant composition comprises the step of irradiating a laser or plasma having an intensity of 400 mW/cm 2 or less to the encapsulant composition, wherein the surface hardening degree is increased by the action of radicals generated by the light irradiation. It provides a method for photopolymerization of a compound containing an ethylenically unsaturated double bond.
  • the solid-state dielectric constant measured in the cured film by curing the encapsulant composition according to one embodiment to the state of an organic cured film may be 2.70 or less.
  • the encapsulant composition having a dielectric constant of 2.70 or less measured as a solid phase upon curing is suitable for protecting the coating film from external static electricity to prevent malfunction of the light emitting device.
  • an organic cured film including a cured product of the above-described composition.
  • the thickness of the organic cured film for the encapsulant may be 0.5 ⁇ 100um, 1 ⁇ 90um, or 5 ⁇ 70um.
  • the organic cured film for the encapsulant may have a transmittance of 97.0% or more measured at a wavelength of 400 nm.
  • the organic cured film for the encapsulant is positioned close to the organic light emitting device in the screen display device, and when the transmittance is satisfied, clear visibility can be provided to the user.
  • an encapsulant may include an organic cured film for the encapsulant; and an inorganic layer including a metal.
  • the inorganic layer may include a metal component.
  • the inorganic layer may also be a thin metal film.
  • the inorganic layer may include one or more oxides or nitrides selected from the group consisting of Al, Zr, Ti, Hf, Ta, In, Sn, Zn, Ce, and Si.
  • the inorganic layer may be formed by vapor deposition. In this case, a specific deposition process is not particularly limited.
  • the inorganic layer may have a SiNx thin film and/or an SiOx thin film.
  • a light emitting device having at least one surface of the organic cured film of the encapsulant composition.
  • the configuration of the light emitting device is not particularly limited, and may have a configuration known to those of ordinary skill in the art.
  • the cured film is, for example, printing ink, printing plate, encapsulant, photoresist for electronic devices, electroplating resist, etching resist, liquid and dry film, solder resist, resist for manufacturing a color filter for various display applications, plasma- Magnetic as a resist for creating structures in the manufacturing process of display panels, electroluminescent displays and LCDs, compositions for making spacers for LCDs, compositions for holographic data storage (HDS), compositions for encapsulating electrical and electronic components, Recording materials, micromechanical components, waveguides, optical switches, plating masks, etching masks, color correction systems, fiberglass cable coatings, for producing screen printing stencils, for producing three-dimensional objects by stereolithography, image recording materials Sequential of printed circuit boards as photoresist material for holographic recording, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules, as photoresist materials for UV and visible laser induced imaging systems It can be used as a photoresist
  • the transmittance of the cured film was measured using a UV-Vis spectrometer in accordance with ASTM D1003, and showed a value of 95% or more, and it can be seen that the surface hardening degree shows a significantly improved curing difference compared to the existing one.
  • an electronic device in which the cured film is an encapsulation film material or an overcoat material.
  • Non-limiting examples of the substrate of the cured film include a substrate for electronic components, a substrate having a predetermined wiring pattern formed thereon, and the like.
  • the substrate include a glass or plastic substrate or a glass or plastic substrate coated with silicon, silicon nitride, silicon oxide, titanium, tantalum, palladium, titanium tungsten, copper, chromium, aluminum, AlNd, ITO, IGZO, etc. have.
  • compositions of Examples and Comparative Examples were prepared by using the photocurable monomers shown in Table 1 to vary the content as shown in Table 2 below. 3 to 4 parts by weight of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide as an initiator based on 100 parts by weight of the total of the first and second monomer groups were blended.
  • Short-wavelength UV light (UV LED light source, total irradiation time: 400mW/cm 2 , light quantity: 1,000mJ/cm 2 ) was irradiated at room temperature to cure the composition to a thickness of 8um.
  • Tables 1 to 3 below show physical properties measured using the following evaluation items for raw materials, encapsulant compositions, or cured products.
  • Liquid permittivity The dielectric constant at 10 KHz was measured at room temperature using a Dielectric Constant Meter model 871, and C values are shown in Tables 1 and 3 below.
  • the solid-state dielectric constant sample was cured by spin-coating the composition on a Cr glass (Cr thickness 1600 ⁇ ) substrate (thickness 8.0um, exposure dose 1000mJ/cm2), and then Al (Al thickness 1000 ⁇ , Al size 3.0*3.0mm2) was applied on the organic cured film. deposited.
  • Jetting spreadability of organic composition When the encapsulant composition was jetted at an inkjet head temperature of 35 degrees and a volume of 13 picoliter, spreadability was evaluated through the drop size change after curing for 5 minutes compared to the initial drop size. For reference, when the spreadability is about 110 ⁇ 130%, the coating surface formation is good. If the spreadability is low, the drop does not spread and the surface cannot be formed properly. If the spreadability is too high, the encapsulant composition flows down before UV curing to form a normal surface. I can't do it, so it's not advisable
  • Example 1 A2 40 B1 50 B4 10 - - 4.56 8.5
  • Example 2 A2 40 B1 55 B5 5 - - 4.56 8.7
  • Example 3 A2 60 B2 35 B11 5 - - 4.76 10.0
  • Example 4 A4 65 B2 25 B4 10 - - 4.76 9.4
  • Example 5 A4 65 B2 20 B5 15 - - 4.76 9.7
  • Example 6 A6 50 B1 45 B4 5 - - 4.56 7.9
  • Example 7 A6 60 B2 35 B5 10 - - 4.76 8.3
  • Example 8 A1 80 B2 15 B4 5 - - 4.76 12.1
  • Example 9 A1 80 B1 15 B5 5 - - 4.56 12.3 Comparative
  • Example 9 A1 80 B1 15 B5 5 - - 4.56 12.3 Comparative
  • Example 9 A1 80 B1 15 B5 5 - - 4.56 12.3 Comparative
  • Example 9 A1 80 B1 15 B5 5 - - 4.56
  • the [C]/[O] ratio in Table 2 is the ratio of the total number of carbons to the total number of oxygen in the composition calculated from carbon and oxygen of the monomer of the first monomer group and carbon and oxygen of the monomer of the second monomer group. , means the calculated value of a/c in the formula C a H b O c .
  • the dielectric constant of the encapsulant compositions according to Examples 1 to 9 which includes a composition appropriately formulated in consideration of compatibility characteristics between curing characteristics and dielectric constant, is unblended or improperly formulated composition It can be seen that a value smaller than the dielectric constant of the encapsulant compositions according to Comparative Examples 1 to 12 is included. Specifically, Examples 1 to 9 showed a dielectric constant value within a range of 3.39 to 4.03, whereas Comparative Examples 1 to 12 showed a dielectric constant value within a range of 4.22 to 5.71.
  • the encapsulant composition according to Examples 1 to 9 which includes a composition appropriately formulated in consideration of the compatibility between curing characteristics and dielectric constant, has a low dielectric constant was found to be improved by more than 12% and up to 26% compared to the reference value (D, 4.56).
  • Equation 1 of Table 3 above is related to the C/O ratio item of Table 2, and in the encapsulant composition according to Examples 1 to 9, the C/O ratio is in the range of 7.9 or more and 12.3 or less. While the calculated value of 1 suggests 12% or more and a maximum of 26%, in the encapsulant compositions according to Comparative Examples 1 to 12, wherein the C/O ratio is within a relatively low range of 4.1 to 6.8, the calculated value of Formula 1 is 7% or less It can be confirmed from the fact that

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  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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Abstract

La présente invention concerne une composition d'encapsulation et une diode électroluminescente comprenant un film dur organique de la composition d'encapsulation, la composition d'encapsulation comprenant : un premier groupe monomère ; un second groupe monomère ; et un initiateur, le premier groupe monomère comprenant au moins un premier composé monomère, le premier composé monomère ayant un groupe terminal acrylique et comprenant un composé hydrocarboné insaturé à base d'éthylène représenté par la formule 2, le second groupe de monomères comprenant deux ou plus de deux seconds composés monomères, les seconds composés monomères ayant chacun un groupe terminal acrylique et un composé hydrocarboné insaturé à base d'éthylène représenté par la formule 3, le premier groupe de monomères ayant une première permittivité de 2,90 à 4,45 et le second groupe de monomères ayant une seconde permittivité de 4,46 à 8,20.
PCT/KR2021/007436 2020-06-15 2021-06-15 Composition d'encapsulation et diode électroluminescente WO2021256814A1 (fr)

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