WO2019066605A1 - 유기전자소자의 봉지 방법 - Google Patents

유기전자소자의 봉지 방법 Download PDF

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Publication number
WO2019066605A1
WO2019066605A1 PCT/KR2018/011618 KR2018011618W WO2019066605A1 WO 2019066605 A1 WO2019066605 A1 WO 2019066605A1 KR 2018011618 W KR2018011618 W KR 2018011618W WO 2019066605 A1 WO2019066605 A1 WO 2019066605A1
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WO
WIPO (PCT)
Prior art keywords
ink composition
organic electronic
electronic device
present application
organic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2018/011618
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English (en)
French (fr)
Korean (ko)
Inventor
최국현
김준형
우유진
유미림
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LG Chem Ltd
Original Assignee
LG Chem Ltd
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Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to US16/651,102 priority Critical patent/US12096648B2/en
Priority to EP18862640.2A priority patent/EP3683854B1/en
Priority to CN201880062751.2A priority patent/CN111164779B/zh
Priority to JP2020517975A priority patent/JP7055282B2/ja
Publication of WO2019066605A1 publication Critical patent/WO2019066605A1/ko
Anticipated expiration legal-status Critical
Priority to JP2022010977A priority patent/JP2022048249A/ja
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • 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
    • C09D11/30—Inkjet printing inks
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
    • H10K71/421—Thermal treatment, e.g. annealing in the presence of a solvent vapour using coherent electromagnetic radiation, e.g. laser annealing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/351—Thickness

Definitions

  • the present invention relates to an organic electronic device encapsulation method and an organic electronic device.
  • An organic electronic device refers to an apparatus that includes an organic material layer that generates holes and electrons to generate an alternating current. Examples thereof include a photovoltaic device, a rectifier, A transmitter and an organic light emitting diode (OLED).
  • OLEDs Organic light emitting diodes
  • OLEDs are expected to be applied in various fields covering various portable devices, monitors, notebooks, and televisions because of their excellent space utilization.
  • OLEDs In commercialization of OLEDs and expansion of applications, the main problem is durability. Organic materials and metal electrodes contained in OLEDs are very easily oxidized by external factors such as moisture. Thus, products containing OLEDs are highly sensitive to environmental factors. Accordingly, various methods have been proposed to effectively block penetration of oxygen or moisture from the outside into organic electronic devices such as OLEDs.
  • the present invention relates to a sealing method of an organic electronic device, which is capable of effectively blocking moisture or oxygen introduced from an outside to an organic electronic device, has excellent flatness of the sealing film, has excellent durability reliability, A method of sealing an organic electronic device is provided.
  • the present application relates to an encapsulating method of an organic electronic device.
  • the encapsulation method includes forming a sealing film on the organic electronic device.
  • the sealing film may have the same meaning as the organic layer described later, and may be encapsulated so as to cover the entire surface of the organic electronic device formed on the substrate.
  • An exemplary encapsulation method can include applying an ink composition on a substrate on which the organic electronic device is formed and applying vibration to the applied ink composition.
  • the encapsulating film described above can be formed by the ink composition.
  • the vibration is 0.5 to 150 KHz.
  • the sealing film by applying vibration to the ink composition applied on the element, the sealing film can be formed with excellent flatness without a space between the pattern printed by the ink composition and the pattern.
  • the present application provides a method for realizing excellent reliability even when the nozzle is slipped or clogged.
  • the application of the present application can prevent line unevenness caused by clogging of a coating nozzle when applying an ink composition, and can remove minute bubbles in the ink composition.
  • the present application can prevent a dark spot that may occur in an organic electronic device due to the above-described effect, and can prevent display defects due to stains.
  • the step of applying the vibration is performed in the range of 0.001 to 300 seconds, 0.005 to 290 seconds, 0.01 to 280 seconds, 1 to 270 seconds, 30 to 260 seconds, 50 to 250 seconds, or 150 to 245 seconds .
  • the present application can maintain the flatness of the applied ink composition to be excellent, reduce the time and cost of the process, and increase the efficiency.
  • the step of applying the ink composition may proceed in the range of 50 dpi to 1000 dpi. That is, the ink composition of the present application is used as an ink for inkjet printing so that 50 to 1000 dots per inch can be printed. By adjusting the above-described numerical value, the present application can precisely print an ink composition on a substrate.
  • the applied ink composition may have a thickness of 2 to 15 ⁇ ⁇ or 5 to 13 ⁇ ⁇ .
  • the thickness is a thickness range in which the sealing film formed on the device can sufficiently block the moisture and realize the flatness of the sealing film in the planarization process. Further, it may be a thickness in which optimum flatness is realized at the above-described vibration intensity and / or vibration time.
  • the step of applying the ink composition may include forming two or more print patterns extending in one direction.
  • the ink composition may form two or more print patterns by inkjet printing, and the print pattern may include a primary print pattern 1 and a secondary print pattern 1 as shown in Fig. 1 .
  • Fig. 1 shows an illustrative drawing in which seven print patterns are formed although not shown separately.
  • the print pattern may be formed of two or more ink composition dots, wherein the pitch of the dots is 10 to 250 ⁇ ⁇ , 12 to 230 ⁇ ⁇ , 15 to 180 ⁇ ⁇ , 18 to 140 ⁇ ⁇ , 22 to 110 ⁇ ⁇ , or Mu] m to 35 [mu] m to 90 [mu] m. That is, the print pattern 1 may be formed by collecting two or more dots, and the pitch between the dot and the dot may be the above range.
  • the interval (I) of 10 to 250 mu m, 50 to 230 mu m, 80 to 210 mu m, 110 to 190 mu m, or 130 to 185 mu m may exist between the printed patterns extending in the one direction.
  • the spacing may be an interval that exists prior to applying the vibration after the applying step.
  • two or more print patterns extending in one direction may be formed due to the characteristics of ink-jet printing, and there may be a dot pitch required for forming the one print pattern.
  • the above-mentioned vibration By adjusting the strength, it is possible to manufacture a sealing film having excellent durability and reliability.
  • the sealing method may further comprise curing the applied ink composition.
  • the curing step may include irradiating light.
  • the curing is 250nm to 450nm, 300nm to 450nm, 320 nm to 425 nm, 355 nm to 400 nm, or 380nm to the light of one wavelength from 0.3 to 6, the amount of light or 0.5 J / cm 2 of the 398nm range Lt; 2 > to 5 J / cm < 2 >.
  • the present application can prevent the device from being damaged by light in curing the ink composition applied on the organic electronic device.
  • the sealing method may further comprise applying heat to the applied ink composition.
  • the step of applying heat may proceed before and / or after the curing of the applied ink composition. That is, the step of applying heat may proceed before or after the applied ink composition is cured, and may proceed more than two times before and after curing. Further, in one example, the step of applying heat may be performed simultaneously with the step of applying vibration to the applied ink composition, or may be carried out separately.
  • the present application includes a step of heating the applied ink composition for encapsulation of an organic electronic device before or after curing, thereby minimizing the outgassing generated from the ink composition while improving the flatness of the sealing film formed on the organic electronic device can do. By minimizing the outgassing, the present application is able to prevent physical and chemical damage to the device resulting from the ink composition applied directly onto the organic electronic device.
  • the step of applying the heat may be carried out at a temperature in the range of 20 ° C to 230 ° C, 23 ° C to 200 ° C, or 24 ° C to 164 ° C.
  • the step of applying heat may be carried out for any one of 1 to 40 minutes or 3 to 29 minutes.
  • by adjusting the temperature or the time it is possible to reduce the amount of outgass while realizing excellent flatness when the ink composition applied on the element forms an encapsulating film, and the element is damaged by the heating step .
  • the step of applying heat may be performed only once before curing of the ink composition, or may be conducted twice or more before and after curing.
  • the step of applying heat may be performed at a temperature of 80 to 150 DEG C, 88 to 142 DEG C, 92 to 137 DEG C, or 96 to 123 DEG C for 1 to 40 minutes or 2 to 35 minutes Time.
  • the step of applying heat may be performed at a temperature within a range of 20 to 110 ⁇ ⁇ , 22 to 98 ⁇ ⁇ , 23 to 68 ⁇ ⁇ , 24 to 58 ⁇ ⁇ , or 28 to 37 ⁇ ⁇ , 40 minutes, 2 to 35 minutes, or 6 to 15 minutes.
  • the heating temperature before the curing is somewhat high, partial curing of the ink composition may proceed or a side reaction may occur and it may be difficult to form a sealing film of desired physical properties.
  • the curing of the ink composition may proceed, and after the curing step, the ink composition may be cured at a temperature ranging from 50 ⁇ to 230 ⁇ , 55 ⁇ to 180 ⁇ , 58 ⁇ to 178 ⁇ , 60 ⁇ to 172 ⁇ , 62 ⁇ to 167 ⁇ , 156 DEG C for 1 minute to 40 minutes, 2 minutes to 35 minutes, or 2 minutes to 20 minutes.
  • the ratio (T2 / T1) of the temperature (T2) at which heat is applied after curing to the temperature (T1) to which heat is applied before curing is 1.15 to 8, 1.3 to 7.8, 1.8 to 7.2, 2.1 to 6.8, To 6.3 or 3.6 to 5.8.
  • the application of the present application can control the heating temperature and / or the time according to the timing of applying the heat as described above, so that when the ink composition applied on the device forms an encapsulating film, the outgassing amount can be reduced while realizing excellent flatness , It is possible to prevent the element from being damaged by the heating step, and to prevent some curing or side reaction of the applied composition.
  • the sealing method in the present application is a method of forming a reflective electrode or a reflective electrode on a substrate such as a glass or polymer film, for example, by vacuum evaporation or sputtering, Forming a transparent electrode, and forming an organic material layer on the reflective electrode to form an organic electronic device.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron injecting layer, and / or an electron transporting layer.
  • a second electrode is further formed on the organic material layer.
  • the second electrode may be a transparent electrode or a reflective electrode.
  • the manufacturing method of the present application may further include forming an inorganic layer on the first electrode, the organic material layer, and the second electrode formed on the substrate. Thereafter, as described above, an ink composition is applied to cover the organic electronic device on the substrate to form a sealing film (organic layer).
  • an ink composition is applied to cover the organic electronic device on the substrate to form a sealing film (organic layer).
  • the step of forming the organic layer is not particularly limited, and the ink composition may be applied to the entire surface of the substrate by inkjet printing, gravure, spin coating, screen printing or reverse offset printing Can be used.
  • applying the ink composition may include ejecting the ink composition using an inkjet apparatus.
  • the inkjet process can be applied to encapsulating or encapsulating an organic electronic device such as, for example, an OLED or the like.
  • the term " organic electronic device " refers to an article or apparatus having a structure including an organic material layer that generates alternating electric charges using holes and electrons between a pair of electrodes facing each other, but are not limited to, photovoltaic devices, rectifiers, transmitters, and organic light emitting diodes (OLEDs).
  • the organic electronic device may be an OLED.
  • the ink composition may be of a non-solvent type.
  • the ink composition may be a photocurable composition.
  • the material of the ink composition applied to the sealing method in the present application is not particularly limited. However, considering the flatness characteristics, the outgas characteristics, the ink spreadability, and the reliability of the printing pattern of the present application, With the above specific composition, a sealing film having excellent durability can be formed by the sealing method described above.
  • Exemplary ink compositions may include compounds having an epoxy compound and an oxetane group.
  • the epoxy compound may be a photocurable or thermosetting compound.
  • the oxetane group-containing compound may be contained in an amount of 45 to 145 parts by weight, 48 to 143 parts by weight or 63 to 132 parts by weight based on 100 parts by weight of the epoxy compound.
  • the present application can form an organic layer by an ink-jet method on an organic electronic device, the applied ink composition has excellent spreadability in a short time, and has excellent curing sensitivity after curing Can be provided.
  • the ink composition may include a photoinitiator.
  • the ink composition together with the above-mentioned epoxy compound and oxetane group-containing compound can realize excellent adhesion strength and curing sensitivity as well as fairness as an ink composition.
  • the epoxy compound may be at least bifunctional. That is, two or more epoxy functional groups may be present in the compound.
  • the epoxy compound realizes excellent heat resistance at high temperature and high humidity by realizing a suitable degree of crosslinking in a sealing material.
  • the epoxy compound may include a compound having a cyclic structure in the molecular structure and / or a linear or branched aliphatic compound. That is, the ink composition of the present application may contain at least one of a compound having a cyclic structure in the molecular structure and a linear or branched aliphatic compound as an epoxy compound, and may be included together.
  • a compound having a cyclic structure in the molecular structure may have a ring constituent atom within the molecular structure in the range of 3 to 10, 4 to 8, or 5 to 7, and the cyclic structure in the compound is present in the molecule in an amount of 2 or more, .
  • the linear or branched aliphatic compound is used in an amount of 20 parts by weight or more, less than 205 parts by weight, or less than 23 parts by weight based on 100 parts by weight of the compound having a cyclic structure
  • the ink composition is applied to the ink composition in a range of from 40 to 20 parts by weight, from 30 to 203 parts by weight, 34 to 202 parts by weight, 40 to 201 parts by weight, 60 to 200 parts by weight or 100 to 173 parts by weight, .
  • the linear or branched aliphatic compound may have an epoxy equivalent of from 120 g / eq to 375 g / eq or from 120 g / eq to 250 g / eq.
  • the present invention can prevent the viscosity of the composition from becoming too high, making the inkjet process impossible, while improving the degree of completion of curing after curing of the sealing material.
  • the epoxy compound may have an epoxy equivalent of 50 to 350 g / eq, 73 to 332 g / eq, 94 to 318 g / eq, or 123 to 298 g / eq.
  • the oxetane group-containing compound or epoxy compound has a weight average molecular weight of 150 to 1,000 g / mol, 173 to 980 g / mol, 188 to 860 g / mol, 210 to 823 g / mol, 330 to 780 g / / mol.
  • the present application provides an excellent printing property when applied to inkjet printing, and also provides moisture barrier property and excellent curing sensitivity by controlling the epoxy equivalent of the epoxy compound to a low level or controlling the weight average molecular weight of the compound having the oxetane group to a low level can do.
  • the weight average molecular weight may mean a value converted to standard polystyrene measured by GPC (Gel Permeation Chromatograph).
  • the epoxy equivalent is grams (g / eq) of the resin containing one gram equivalent of epoxy group, and can be measured according to the method defined in JIS K 7236.
  • the oxetane group-containing compound may have a boiling point in the range of 90 to 300 ⁇ ⁇ , 98 to 270 ⁇ ⁇ , 110 to 258 ⁇ ⁇ , or 138 to 237 ⁇ ⁇ .
  • the present invention can provide a sealing material which is excellent in water resistance from the outside while suppressing outgas and preventing damage to the device while realizing excellent printing property even at high temperature in an inkjet process Can be provided.
  • the boiling point may be measured at 1 atm, unless otherwise specified.
  • the compound having a cyclic structure in the molecular structure may be exemplified by an alicyclic epoxy compound.
  • the compound may be selected from 3,4-epoxycyclohexylmethyl 3 ', 4'-epoxycyclohexanecarboxylate (EEC) and derivatives, dicyclopentadiene dioxide and derivatives, vinylcyclohexene dioxide and derivatives, 1,4 -Cyclohexanedimethanol bis (3,4-epoxycyclohexanecarboxylate) and derivatives, but are not limited thereto.
  • EEC 3,4-epoxycyclohexylmethyl 3 ', 4'-epoxycyclohexanecarboxylate
  • dicyclopentadiene dioxide and derivatives vinylcyclohexene dioxide and derivatives
  • 1,4 -Cyclohexanedimethanol bis (3,4-epoxycyclohexanecarboxylate) and derivatives, but are not limited thereto
  • the oxetane group-containing compound is not limited in its structure as long as it has the oxetane functional group.
  • the straight chain or branched aliphatic epoxy compound may be aliphatic glycidyl ether, 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, Propyleneglycol diglycidyl ether, diethylene glycol diglycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, or neopentyl glycol diglycidyl ether. But is not limited thereto.
  • the ink composition may further comprise a photoinitiator.
  • the photoinitiator may be a cationic photoinitiator. Further, the photoinitiator may be a compound absorbing a wavelength in the range of 200 nm to 400 nm.
  • cationic photopolymerization initiator known materials can be used in the art, and examples thereof include a cation moiety including an aromatic sulfonium, an aromatic iodonium, an aromatic diazonium or an aromatic ammonium, and a cation moiety including AsF 6 - , SbF 6 - , PF 6 - , or a tetrakis (pentafluorophenyl) borate.
  • onium salt or organometallic salt series ionized cationic initiators or organosilanes or latent sulfonic acid series or nonionic cationic photopolymerization initiators may be used.
  • diaryliodonium salt, triarylsulfonium salt or aryldiazonium salt can be exemplified, and the initiation of the organometallic salt series
  • the initiator of the organosilane series include o-nitrobenzyl triaryl silyl ether, triaryl silyl peroxide, and the like.
  • an acyl silane, and examples of the initiator of the latent sulfuric acid series include, but are not limited to,? -Sulfonyloxy ketone or? -Hydroxymethylbenzoin sulfonate, and the like .
  • the sealing material composition of the present application may include a photoinitiator containing an iodonium salt or a sulfonium salt as a photoinitiator in the specific composition described above, so as to be suitable for use in sealing an organic electronic device by an inkjet method.
  • a photoinitiator containing an iodonium salt or a sulfonium salt as a photoinitiator in the specific composition described above, so as to be suitable for use in sealing an organic electronic device by an inkjet method.
  • the sealing material composition according to the above composition is sealed directly on the organic electronic device, it is possible to prevent chemical damage from being applied to the device due to a small amount of generated outgas.
  • the photoinitiator is also excellent in solubility and can be suitably applied to an inkjet process.
  • the photoinitiator may be included in an amount of 1 to 15 parts by weight, 2 to 13 parts by weight, or 3 to 11 parts by weight based on 100 parts by weight of the epoxy compound.
  • the ink composition may further comprise a surfactant.
  • the ink composition contains a surfactant, and thus can be provided as a liquid ink having improved spreadability.
  • the surfactant may comprise a polar functional group.
  • the polar functional group may include, for example, a carboxyl group, a hydroxyl group, a phosphate, an ammonium salt, a carboxylate group, a sulfate or a sulfonate.
  • the surfactant may be a non-silicone surfactant or a fluorine surfactant.
  • the non-silicone surfactant or the fluorine surfactant is applied together with the above-mentioned compound having an epoxy compound and an oxetane group to provide excellent coating properties on the organic electronic device.
  • a surfactant containing a polar reactive group since the affinity of the surfactant with other components of the ink composition is high, it is possible to participate in the curing reaction, thereby realizing an excellent effect in terms of adhesion.
  • a hydrophilic fluorosurfactant or a non-silicon surfactant may be used to improve the coating property of the substrate.
  • the surfactant may be a polymer type or an oligomer type fluorine type surfactant.
  • Glide 110, Glide 130, Glide 460, Glide 440, Glide 450 or RAD 2500 from TEGO, Megaface F-251, F-281 from DaiNippon Ink & Chemicals, F-562, F-562, F-570 and F-571, or Surflon S-111 and S-112 of Asahi Glass Co., , Fluorad FC-93, FC-95, FC-98, FC-129 and FC-135 of Sumitomo 3M, S-113, S-121, S- FSK, FSN-100 and FSO from BYK, and BYK-350, BYK-354, BYK-355, BYK-356, BYK-358N, BYK-354, BYK- -359, BYK-361N, BYK-381, BYK-388, BYK-392, BYK
  • the surfactant is used in an amount of 0.1 to 10 parts by weight, 0.05 to 10 parts by weight, 0.1 to 10 parts by weight, 0.5 to 8 parts by weight or 1 to 4 parts by weight based on 100 parts by weight of the epoxy compound .
  • the present application allows the ink composition to be applied to an inkjet method to form an organic layer of a thin film.
  • the ink composition may further comprise a photosensitizer to compensate for curing at a long wavelength activation energy line of 300 nm or more.
  • the photosensitizer may be a compound that absorbs a wavelength in the range of 200 nm to 400 nm.
  • the photosensitizer examples include anthracene compounds such as anthracene, 9,10-dibutoxyanthracene, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene and 2-ethyl-9,10-dimethoxyanthracene; Benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl- Benzophenone-based compounds such as dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Acetophenone; Ketone-based compounds such as dimethoxyacetophenone, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one and propanone; Perylene; Fluorene-based compounds such as 9-fluorenone, 2-ch
  • Thioxanthone compounds such as xanthone and 2-methylxanthone;
  • Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; (9-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds;
  • Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone;
  • Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide;
  • the photosensitizer may be contained in the range of 28 to 40 parts by weight, 31 to 38 parts by weight or 32 to 36 parts by weight based on 100 parts by weight of the photoinitiator described later.
  • the present invention can prevent the photosensitizer from dissolving and lowering the adhesion force while realizing a synergistic effect of curing sensitivity at a desired wavelength.
  • the ink composition of the present application may further comprise a coupling agent.
  • the present application can improve the adhesion of the cured product of the ink composition to an adherend or the moisture permeability of the cured product.
  • the coupling agent may include, for example, a titanium-based coupling agent, an aluminum-based coupling agent, and a silane coupling agent.
  • silane coupling agent examples include 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxypropyl Epoxy silane coupling agents such as methyl silane and 2- (3,4-epoxycyclohexyl) ethyl trimethoxy silane; Mercapto-based silane coupling agents such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane and 11-mercaptoundecyltrimethoxysilane; Aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxymethylsilane, N-phenyl-3-aminopropyltrimethoxysilane, N-methylaminopropyltrimethoxysilane, N
  • the coupling agent may be contained in an amount of 0.1 to 10 parts by weight or 0.5 to 5 parts by weight based on 100 parts by weight of the epoxy compound. Within the above range, the present application can achieve the effect of improving the adhesion by the addition of the coupling agent.
  • the ink composition of the present application may, if necessary, contain a moisture adsorbent.
  • a moisture adsorbent may be used to mean a component capable of adsorbing or removing moisture or moisture introduced from the outside through physical or chemical reaction or the like. Means a water-reactive adsorbent or a physical adsorbent, and mixtures thereof are also usable.
  • the specific kind of the moisture adsorbent that can be used in the present application is not particularly limited.
  • P 2 O 5 phosphorus pentoxide
  • zeolite, zirconia or montmorillonite may be mentioned.
  • the ink composition of the present application may contain the moisture adsorbent in an amount of 5 to 100 parts by weight, 5 to 80 parts by weight, 5 to 70 parts by weight or 10 to 30 parts by weight based on 100 parts by weight of the epoxy compound have.
  • the ink composition of the present application can preferably control the content of the moisture adsorbent to 5 parts by weight or more so that the ink composition or the cured product thereof exhibits excellent moisture and moisture barrier properties.
  • the present application can control the content of the moisture adsorbent to 100 parts by weight or less to provide a thin film encapsulation structure.
  • the ink composition may further comprise an inorganic filler, if desired.
  • an inorganic filler that can be used in the present application is not particularly limited, and for example, clay, talc, alumina, calcium carbonate, silica, or the like, or a mixture of two or more species may be used.
  • the ink composition of the present application may contain 0 to 50 parts by weight, 1 to 40 parts by weight, 1 to 20 parts by weight, or 1 to 10 parts by weight of inorganic filler per 100 parts by weight of the epoxy compound have.
  • the present application can provide an encapsulating structure having excellent moisture or moisture barrier properties and mechanical properties by controlling the inorganic filler to preferably 1 part by weight or more. Further, by controlling the content of the inorganic filler to 50 parts by weight or less, the present invention can provide a cured product exhibiting excellent moisture barrier properties even when formed into a thin film.
  • the ink composition according to the present application may contain various additives in addition to the above-mentioned composition within the range not affecting the effects of the above-described invention.
  • the ink composition may contain an antifoaming agent, a tackifier, a UV stabilizer, or an antioxidant in an appropriate amount depending on the intended physical properties.
  • the ink composition may be in a liquid state at room temperature, for example, at 15 ⁇ ⁇ to 35 ⁇ ⁇ or at about 25 ⁇ ⁇ .
  • the ink composition may be in liquid form in the form of a solvent.
  • the ink composition may be applied to encapsulate an organic electronic device, and specifically, the ink composition may be an ink composition that can be applied to encapsulate the front surface of an organic electronic device.
  • the ink composition has a liquid phase at room temperature, so that the composition can be sealed on the side of the organic electronic device by the ink jet method.
  • the ink composition may have a viscosity of less than or equal to 50 cPs, 1 to 46 cPs, 3 to 44 cPs, as measured by Brookfield DV-3 at 25 ° C, 90% torque and a shear rate of 100 rpm cPs, 4 to 38 cPs, 5 to 33 cPs, or 14 to 24 cPs.
  • the present application can provide a sealing material for a thin film by controlling the viscosity of the composition within the above range, thereby improving the coating property at the time of application to the organic electronic device.
  • the ink composition may have a light transmittance of 90% or more, 92% or more, or 95% or more in the visible light region after curing.
  • the present application provides an organic electronic device of high resolution, low power consumption, and long life by applying an ink composition to a top emission type organic electronic device.
  • the ink composition may not contain the above-described moisture adsorbent or inorganic filler.
  • the ink composition of the present application may have a contact angle to glass of no more than 30, no more than 25, no more than 20, or no more than twelve degrees.
  • the lower limit is not particularly limited, but may be 1 deg. Or 3 deg. Or more.
  • the contact angle may be measured by applying a drop of the ink composition onto glass using a Sessile Drop measurement method, and may be an average value measured after 5 times of application.
  • An exemplary organic electronic device 3 as shown in Fig. 3, comprises a substrate 31; An organic electronic device 32 formed on the substrate 31; And an organic layer 33 sealing the front surface of the organic electronic device 32.
  • the organic electronic device may be manufactured by the sealing method described above, but is not limited thereto.
  • Fig. 2 is an enlarged sectional view of Fig. 1.
  • the organic electronic device includes, on a substrate on which an organic electronic device is formed, a primary pattern 1 extending in one direction and a primary pattern 1 extending in one direction,
  • the ratio h / H of the height h of the groove portion between the primary pattern and the secondary pattern with respect to the organic layer thickness H in the state that the ink composition is cured in the form of an organic layer including the adjacent secondary pattern 1 100 may be less than 30%, less than 29%, or less than 28%.
  • the lower limit of the ratio is not particularly limited and may be 0%, 1%, or 5%.
  • forming adjacent to each other means to be located in contact with each other in a direction perpendicular to the direction extending in one direction in the primary pattern extending in one direction.
  • one direction of the primary pattern and the secondary pattern may be in the same direction.
  • the present application can realize excellent flatness of a sealing film formed of an ink composition by controlling the above ratio, and such sealing film can be also excellently adhered to an inorganic layer to be attached to an upper part to be described later.
  • the primary and secondary patterns may be formed by printing one droplet of the ink composition to form two or more dot lines. More specifically, the ink composition dot may be printed in a straight line or a rectangular shape extending in one direction And the shape of the pattern is not particularly limited.
  • the present application can form the above primary and secondary patterns simultaneously or separately.
  • the primary pattern and the secondary pattern are names designated arbitrarily in order to distinguish patterns from patterns, and do not mean the order or number of patterns.
  • the distance between the formation point of the primary pattern and the formation point of the secondary pattern may be in the range of 10 ⁇ to 500 ⁇ , 20 ⁇ to 430 ⁇ , 30 ⁇ to 390 ⁇ or 60 ⁇ to 250 ⁇ .
  • the point at which the printing pattern is formed may refer to a point at which the ink composition dot is applied in the inkjet printing.
  • the formation point may mean the center of the primary printing pattern and the center of the secondary printing pattern in consideration of forming a printing pattern in which the plurality of dots spread to extend in one direction, It can mean the center in the direction perpendicular to the extending direction.
  • " center &quot may mean a substantial center, and may have an error of +/- 10 mu m, +/- 5 mu m, or +/- 1 mu m.
  • " vertical &quot may mean substantially vertical, and may also have an error of +/- 10 degrees, +/- 5 degrees, or +/- 1 degree.
  • the organic electronic device may include a first electrode layer, an organic layer formed on the first electrode layer and including at least a light emitting layer, and a second electrode layer formed on the organic layer.
  • the first electrode layer may be a transparent electrode layer or a reflective electrode layer
  • the second electrode layer may also be a transparent electrode layer or a reflective electrode layer.
  • the organic electronic device may include a reflective electrode layer formed on a substrate, an organic layer formed on the reflective electrode layer and including at least a light emitting layer, and a transparent electrode layer formed on the organic layer.
  • the organic electronic device in the present application may be an organic light emitting diode.
  • the organic electronic device according to the present application may be of a top emission type, but is not limited thereto, and may be applied to a bottom emission type.
  • the organic electronic device may further include an electrode of the organic electronic device and an inorganic layer for protecting the light emitting layer.
  • the inorganic layer may be an inorganic protective film.
  • the inorganic layer 35 may be present between the organic electronic device 32 and the organic layer 33 described above.
  • the inorganic layer may be a protective layer by chemical vapor deposition (CVD), and a known inorganic material may be used as the material.
  • CVD chemical vapor deposition
  • the organic electronic device may further include an inorganic layer 34 formed on the organic layer 33.
  • the inorganic layer may be at least one metal oxide, nitride or oxynitride selected from the group consisting of Al, Zr, Ti, Hf, Ta, In, Sn, Zn and Si.
  • the thickness of the inorganic layer may be 0.01 ⁇ to 50 ⁇ or 0.1 ⁇ to 20 ⁇ or 1 ⁇ to 10 ⁇ .
  • the inorganic layer of the present application may be an inorganic material without a dopant, or it may be an inorganic material containing a dopant.
  • the dopant that can be doped is at least one element selected from the group consisting of Ga, Si, Ge, Al, Sn, Ge, B, In, Tl, Sc, V, Cr, Mn, Fe, Co, But is not limited thereto.
  • the thickness of the organic layer may be in the range of 2 ⁇ to 20 ⁇ , 2.5 ⁇ to 15 ⁇ , and 2.8 ⁇ to 9 ⁇ .
  • the present application can provide a thin organic electronic device by providing a thin thickness of the organic layer.
  • the organic electronic device of the present application may include an encapsulation structure 36 comprising the organic layer 33 and the inorganic layers 34 and 35 as described above and the encapsulation structure may include at least one organic layer and at least one inorganic layer And the organic layer and the inorganic layer may be repeatedly laminated.
  • the organic electronic device may have a structure of substrate / organic electronic device / inorganic layer / (organic layer / inorganic layer) n, and n may be a number within a range of 1 to 100.
  • the organic electronic device of the present application may further comprise a cover substrate present on the organic layer.
  • the material of the substrate and / or the cover substrate is not particularly limited, and materials known in the art can be used.
  • the substrate or cover substrate may be a glass, metal substrate, or polymer film.
  • the polymer film may be, for example, a polyethylene terephthalate film, a polytetrafluoroethylene film, a polyethylene film, a polypropylene film, a polybutene film, a polybutadiene film, a polyvinyl chloride film, a polyurethane film, -Propylene copolymer film, an ethylene-ethyl acrylate copolymer film, an ethylene-methyl acrylate copolymer film, or a polyimide film.
  • the sealing film 37 which is present between the cover substrate 38 and the substrate 31 on which the organic electronic device 32 is formed, May be further included.
  • the sealing film 37 may be used for attaching the substrate 31 on which the organic electronic device 32 is formed and the cover substrate 38.
  • the sealing film 37 may be a solid adhesive film or an adhesive film at room temperature But is not limited thereto.
  • the sealing film 37 can seal the front surface of the sealing structure 36 of the above-described organic layer and inorganic layer stacked on the organic electronic device 32.
  • the cover substrate may be a glass, a polymer resin film, or a metal layer.
  • the present invention relates to a sealing method of an organic electronic device using an ink composition, which can effectively block moisture or oxygen introduced into the organic electronic device from the outside, has excellent flatness of the sealing film formed of the ink composition,
  • the present invention provides a method of encapsulating an organic electronic device, which prevents streaking caused by clogging of a coating nozzle when applying an ink composition, removes minute bubbles in the composition, and increases the efficiency of the sealing process.
  • FIG. 1 is a plan view showing a print pattern according to one example of the present invention.
  • FIG. 2 is a cross-sectional view showing a print pattern according to one example of the present invention.
  • Figures 3 and 4 are cross-sectional views illustrating organic electronic devices according to one example of the present invention.
  • a uniform ink composition ink was prepared using the planetary mixer (Kurabo KK-250s).
  • the ink composition was inkjetted on a substrate having an organic electronic device formed thereon using Unijet UJ-200 (Inkjet head-Dimatix 10Pl 256) to form a print pattern.
  • An average pitch of the dots of the ink composition was 40 ⁇ ⁇ to form a print pattern, and an average interval between the print patterns was 180 ⁇ ⁇ to form an organic layer pattern.
  • the printed pattern applied on the substrate was subjected to vibration for 0.01 seconds at an intensity of 40 KHz using a vibrating device.
  • the applied print pattern was subjected to heat treatment at 100 DEG C for 3 minutes.
  • the ink composition was irradiated with UV of 1 J / cm < 2 > at an intensity of 1000 mW / cm < 2 > under a relative humidity of 5% to cure the organic electronic device.
  • An organic electronic device was prepared in the same manner as in Example 1, except that the applied printing pattern was subjected to vibration for 10 seconds.
  • An organic electronic device was prepared in the same manner as in Example 1, except that the applied printing pattern was subjected to vibration for 40 seconds.
  • An organic electronic device was prepared in the same manner as in Example 1, except that the applied printing pattern was subjected to vibration for 240 seconds.
  • An organic electronic device was prepared in the same manner as in Example 1, except that the oscillation intensity was changed to 100 KHz.
  • An organic electronic device was prepared in the same manner as in Example 2, except that the vibration intensity was changed to 100 KHz.
  • An organic electronic device was prepared in the same manner as in Example 3, except that the oscillation intensity was changed to 100 KHz.
  • An organic electronic device was prepared in the same manner as in Example 4, except that the oscillation intensity was changed to 100 KHz.
  • a uniform ink composition ink was prepared using the planetary mixer (Kurabo KK-250s).
  • ink-jetting was carried out in the same manner as in Example 4 to encapsulate the organic electronic device to produce an organic electronic device.
  • a uniform ink composition ink was prepared using the planetary mixer (Kurabo KK-250s).
  • ink-jetting was carried out in the same manner as in Example 4 to encapsulate the organic electronic device to produce an organic electronic device.
  • An organic electronic device was manufactured in the same manner as in Example 1, except that no vibration was applied and UV was irradiated after a waiting time of 0.01 seconds after the formation of a print pattern.
  • An organic electronic device was produced in the same manner as in Example 1, except that no vibration was applied and UV was irradiated after a waiting time of 10 seconds after the formation of the print pattern.
  • An organic electronic device was prepared in the same manner as in Example 1, except that no vibration was applied and UV was irradiated after a waiting time of 40 seconds after the formation of the print pattern.
  • An organic electronic device was manufactured in the same manner as in Example 1, except that no vibration was applied and UV was irradiated after a waiting time of 240 seconds after the formation of the print pattern.
  • the ratio h / H x 100 of the height h of the groove between the primary pattern and the secondary pattern to the thickness H of the organic layer was measured and calculated for the cured organic layer prepared in Examples and Comparative Examples .
  • the average thickness of the organic layer was measured.
  • the thickness H and the height h of the groove were measured using an Alpha step (KLA-Tencor).

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Photovoltaic Devices (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/KR2018/011618 2017-09-29 2018-10-01 유기전자소자의 봉지 방법 Ceased WO2019066605A1 (ko)

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US16/651,102 US12096648B2 (en) 2017-09-29 2018-10-01 Method for encapsulating organic electronic element
EP18862640.2A EP3683854B1 (en) 2017-09-29 2018-10-01 Method for encapsulating organic electronic element
CN201880062751.2A CN111164779B (zh) 2017-09-29 2018-10-01 用于封装有机电子元件的方法
JP2020517975A JP7055282B2 (ja) 2017-09-29 2018-10-01 有機電子素子の封止方法
JP2022010977A JP2022048249A (ja) 2017-09-29 2022-01-27 有機電子素子の封止方法

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CN117940265A (zh) * 2021-12-01 2024-04-26 株式会社Lg化学 制造封装膜的方法

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CN111164779B (zh) 2022-12-02
TW201931636A (zh) 2019-08-01
EP3683854B1 (en) 2024-11-27
KR102126702B1 (ko) 2020-06-25
TWI800534B (zh) 2023-05-01
JP2022048249A (ja) 2022-03-25
JP2020535615A (ja) 2020-12-03
EP3683854A1 (en) 2020-07-22
US12096648B2 (en) 2024-09-17
CN111164779A (zh) 2020-05-15
JP7055282B2 (ja) 2022-04-18
KR20190038455A (ko) 2019-04-08
US20200280022A1 (en) 2020-09-03
EP3683854A4 (en) 2020-10-28

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