US20180309089A1 - Compositions and Techniques for Forming Organic Thin Films - Google Patents

Compositions and Techniques for Forming Organic Thin Films Download PDF

Info

Publication number
US20180309089A1
US20180309089A1 US15/955,303 US201815955303A US2018309089A1 US 20180309089 A1 US20180309089 A1 US 20180309089A1 US 201815955303 A US201815955303 A US 201815955303A US 2018309089 A1 US2018309089 A1 US 2018309089A1
Authority
US
United States
Prior art keywords
meth
mol
acrylate monomer
ink composition
curable ink
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.)
Abandoned
Application number
US15/955,303
Other languages
English (en)
Inventor
Elena Rogojina
Teresa A. Ramos
Citra Yuwono
Lorenza Moro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kateeva Inc
Original Assignee
Kateeva Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to TW107113054A priority Critical patent/TWI841527B/zh
Priority to US15/955,303 priority patent/US20180309089A1/en
Application filed by Kateeva Inc filed Critical Kateeva Inc
Assigned to KATEEVA, INC. reassignment KATEEVA, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MORO, LORENZA, YUWONO, CITRA, RAMO, TERESA A., ROGOJINA, ELENA
Assigned to KATEEVA, INC. reassignment KATEEVA, INC. CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR LAST NAME PREVIOUSLY RECORDED AT REEL: 045686 FRAME: 0574. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Assignors: MORO, LORENZA, YUWONO, CITRA, RAMOS, TERESA A., ROGOJINA, ELENA
Publication of US20180309089A1 publication Critical patent/US20180309089A1/en
Assigned to EAST WEST BANK reassignment EAST WEST BANK SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KATEEVA, INC.
Assigned to KATEEVA, INC. reassignment KATEEVA, INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: EAST WEST BANK, A CALIFORNIA BANKING CORPORATION
Assigned to SINO XIN JI LIMITED reassignment SINO XIN JI LIMITED SECURITY AGREEMENT Assignors: KATEEVA, INC.
Assigned to SINO XIN JI LIMITED reassignment SINO XIN JI LIMITED SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KATEEVA CAYMAN HOLDING, INC., KATEEVA, INC.
Assigned to HB SOLUTION CO., LTD. reassignment HB SOLUTION CO., LTD. SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KATEEVA CAYMAN HOLDING, INC.
Priority to US17/809,243 priority patent/US11844234B2/en
Priority to US18/497,917 priority patent/US20240081096A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • 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
    • H01L51/5253—
    • 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
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/34—Nitrides
    • C23C16/345—Silicon nitride
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
    • C23C16/40—Oxides
    • C23C16/403—Oxides of aluminium, magnesium or beryllium
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/50—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating using electric discharges
    • H01L51/004—
    • H01L51/0043—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/873—Encapsulations
    • 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
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • 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
    • H10K85/151—Copolymers
    • 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

  • OLED organic light-emitting diode
  • OLED optoelectronic devices are fabricated from inorganic and organic materials, including various organic thin film emissive materials. Such materials can be susceptible to degradation by water, oxygen and other chemical species in the environment.
  • OLED devices have been encapsulated in order to provide protection against degradation.
  • encapsulation stacks that include alternating inorganic barrier layers and organic planarizing layers have been used to isolate the moisture- and/or oxygen-sensitive materials in OLEDs.
  • inkjet printing can provide several advantages. First, a range of vacuum processing operations can be eliminated because inkjet-based fabrication can be performed at atmospheric pressure. Additionally, during an inkjet printing process, an organic planarizing layer can be localized to cover portions of an OLED substrate over and proximal to an active region, to effectively encase an active region, including lateral edges of the active region.
  • the targeted patterning using inkjet printing results in eliminating material waste, as well as eliminating the need for masks and therefore challenges presented with the alignment and fouling thereof, as well as eliminating additional processing typically required to achieve patterning of an organic layer when utilizing, for example, various vapor deposition processes.
  • compositions of the present teachings can be deposited on a substrate and cured to form an organic layer on a substrate.
  • inkjet deposition can be used for the deposition of an organic thin film composition on a substrate, followed by a curing process to form an organic layer on a substrate.
  • FIG. 1 is a schematic section view of an optoelectronic device, illustrating various aspects of a fabrication.
  • FIG. 2 is a graph of viscosity versus temperature for various embodiments of a first organic monomer composition of the present teachings.
  • FIG. 3 is a graph of viscosity as a function of temperature for various embodiments of a second organic monomer composition of the present teachings.
  • FIG. 4 is a graph of transmission as a function of wavelength for thin films formed from each of an exemplary composition of the present teachings in comparison to the transmission of a glass reference material.
  • FIG. 5 illustrates generally examples of a gas enclosure system for integrating and controlling gas sources such as can be used to establish a controlled process environment, as well as providing a pressurized gas and at least partial vacuum for use with a floatation table.
  • FIG. 6 illustrates generally an isometric view of at least a portion of a system, such as including an enclosed printing system and an enclosed curing system.
  • FIG. 7 is a flow diagram that illustrates generally a process for the fabrication of an organic thin films on various device substrates.
  • the present teachings relate to various embodiments of curable ink compositions, which once deposited and cured, provide a polymeric film over at least a portion of a substrate in an electronic device.
  • Electronic devices on which the polymeric films may be formed include electronic devices having one or more components that are moisture- and/or oxygen-sensitive—that is, one or more components whose performance is negatively affected by reactions with water and/or oxygen in the atmosphere.
  • the polymeric film may be included as a planarizing layer in a multi-layered encapsulation stack, as described in greater detail below.
  • the polymeric films may also be used to improve light extraction for a light-emitting optoelectronic device, to provide thermal dissipation for a heat-generating device, and/or to provide protection from mechanical damage for an electronic device that is susceptible to breaking, including electronic devices that have glass components, such as glass screens.
  • Electronic devices over which the polymeric films can be formed include optoelectronic devices, such as OLEDs, as well as lithium batteries, capacitors, and touch screen devices. Because the polymeric films are flexible, they are suited for use with flexible electronic devices.
  • the polymeric films are disposed over a light-emitting active region of an OLED device substrate.
  • the light-emitting active region of an OLED device can include various materials that degrade in the presence of various reactive species, such as, but not limited by, water vapor, oxygen, and various solvent vapors from device processing. Such degradation can impact the stability and reliability of an OLED device.
  • a multilayered encapsulation stack can be used to protect the OLED, wherein the encapsulation stack includes a film of an inorganic barrier layer adjacent to a polymeric planarizing layer.
  • An encapsulation stack will include at least one such inorganic barrier layer/polymeric planarizing layer pair (“dyad”), but can include multiple stacked dyads.
  • the lowermost layer in the encapsulation stack, which is in contact with at least one substrate of the electronic device can be either an inorganic barrier layer or a polymeric planarizing layer.
  • a polymeric film that is disposed over a light-emitting active region need not be formed directly on the light-emitting active region.
  • the polymeric film can be formed on one of the electrodes between which the light-emitting active region is disposed, on an inorganic barrier layer that forms part of an encapsulation stack, and/or on the surface of an OLED support substrate.
  • a deposition system such as an industrial inkjet printing system, that can be housed in an enclosure configured to provide a controlled process environment can be used.
  • Inkjet printing for the deposition of the curable ink compositions described herein can have several advantages. First, a range of vacuum processing operations can be eliminated, as inkjet-based fabrication can be performed at atmospheric pressure. Additionally, during an inkjet printing process, an ink composition can be localized to cover portions of an electronic device substrate, including portions that are over and proximal to an active region, to effectively encapsulate an active region, including the lateral edges of the active region.
  • the targeted patterning using inkjet printing results in eliminating material waste, as well as eliminating additional processing typically required to achieve patterning of an organic layer, as required, for example, by various masking techniques.
  • curable ink compositions of the present teachings can be deposited by printing over a wide number of OLED devices, such as OLED display devices and OLED lighting devices, to form a uniform planarizing layer.
  • OLED devices such as OLED display devices and OLED lighting devices
  • Such ink compositions can be cured using thermal processing (e.g. bake), by exposure to optical energy, (e.g., UV cure), or electron-beam curing.
  • Some embodiments of the ink compositions can be cured by UV radiation, including UV radiation in the wavelength range of between about 365 nm to about 420 nm.
  • electronic device 50 can be fabricated on substrate 52 .
  • a substrate can include a thin silica-based glass, as well as any of a number of flexible polymeric materials.
  • substrate 52 can be transparent, such as for use in a bottom-emitting optoelectronic device (e.g. OLED) configuration.
  • OLED optoelectronic device
  • One or more layers associated with an electronic device stack, such as various organic or other material can be deposited, inkjet printed, or otherwise formed upon the substrate to provide an active region 54 , such as an electroluminescent region in an OLED. Note that active region 54 in FIG.
  • electronic device 50 is an OLED device, in can include an emissive layer, or other layers, coupled to an anode electrode and a cathode electrode.
  • An anode electrode or a cathode electrode can be coupled to or can include electrode portion 56 that is laterally offset along the substrate 52 from the active region 54 .
  • an inorganic barrier layer 60 A can be provided on electronic device 50 over active region 54 .
  • the inorganic barrier layer can be blanket coated (e.g., deposited) over an entirety, or substantially an entirety of a surface of the substrate 52 , including active region 54 , using, by way of a non-limiting example, plasma enhanced chemical vapor deposition (PECVD).
  • PECVD plasma enhanced chemical vapor deposition
  • examples of inorganic materials useful for fabricating inorganic barrier layer 60 A can include various inorganic oxides, such as one or more of Al 2 O 3 , TiO 2 , HfO 2 , SiO X N Y , inorganic nitrides, such as silicon nitride, or one or more other materials.
  • Adjacent to inorganic barrier layer 60 A is polymeric film 62 A.
  • polymeric film 62 A can be deposited using for example, inkjet printing of a curable ink composition and then curing the ink composition to form the polymeric film.
  • Polymeric film 62 A can serve as a planarizing layer to planarize and mechanically protect the active region 54 , as part of an encapsulation stack that collectively serves to suppress or inhibit moisture or gas permeation into the active region 54 .
  • FIG. 1 illustrates generally a multilayered encapsulation stack configuration having inorganic barrier layer 60 A polymeric film 62 A, a second inorganic barrier layer 60 B, and a second polymeric film 62 B.
  • planarizing layers in an encapsulation stack can serve to prevent the propagation of defects from one inorganic barrier layer into an adjacent inorganic barrier layer.
  • various embodiments of encapsulation stacks can be created to provide the mechanical and sealing properties desired for an electronic device.
  • the order of the fabrication of the layers in the encapsulation stack depicted in FIG. 1 could be reversed, so that a polymeric planarizing layer is first fabricated, followed by the fabrication of an inorganic barrier layer. Additionally, greater or fewer numbers of dyads can be present. For example, a stack having inorganic barrier layers 60 A and 60 B as shown, and a single polymeric planarizing layer 62 A can be fabricated.
  • curable ink compositions that can be used to form polymeric films that remain stable throughout the electronic device fabrication processes, as well as providing long-term stability and function as part of a protective layer for various electronic devices.
  • Curable ink compositions of the present teachings can be readily deposited as a liquid material on a substrate and then cured to form a polymeric thin film thereupon.
  • Various embodiments of such curable ink compositions can include diacrylate monomers, dimethacrylate monomers, monoacrylate monomers, monomethacrylate monomers and combinations thereof as base monomers, as well as various multifunctional crosslinking agents.
  • the phrase “(meth)acrylate” indicates that the recited component may be an acrylate, methacrylate, or a combination thereof.
  • the term “(meth)acrylate monomer” refers to both methacrylate monomers and acrylate monomers.
  • Various embodiments of the curable ink compositions further include cure initiators, such as photoinitiators.
  • compositions described herein are referred to as “ink compositions” because various embodiments of the compositions can be applied using techniques, including printing techniques, by which conventional inks have been applied to substrates.
  • printing techniques include, for example, inkjet printing, screen printing, thermal transfer printing, flexographic printing, and/or offset printing.
  • various embodiments of the ink compositions can also be applied using other coating techniques, such as, for example, spray coating, spin coating, and the like.
  • the ink compositions need not contain colorants, such as dyes and pigments, which are present in some conventional ink compositions.
  • Precision deposition techniques are techniques that apply the ink compositions to a substrate with a high degree of precision and accuracy with respect to the quantity, location, shape, and/or dimensions of the printed ink compositions and the cured polymeric films that are formed therefrom.
  • the precision deposition techniques are able to form blanket coatings of the ink compositions or patterned coatings of the ink compositions that, once cured, form thin polymeric films with highly uniform thicknesses and well-defined edges.
  • the precision deposition coating techniques are able to provide thin polymeric films that meet the requirements of a variety of organic electronic and organic optoelectronic device applications.
  • the required quantity, location, shape, and dimensions for a given precision deposited ink composition and the cured film formed therefrom, will depend on the intended device application.
  • various embodiments of the precision deposition techniques are able to form blanket or patterned films having a thickness of no greater than 10 ⁇ m with a thickness variation of no more than 5% across the film.
  • Inkjet printing in one example of a precision deposition technique is possible.
  • Cured polymeric films made from the ink compositions are stable and flexible.
  • the ink compositions can be formulated to provide cured polymeric films with glass transition temperatures (T g ) that allow them to be subjected to various post-processing techniques. Having a sufficiently high T g is desirable for certain applications, such as applications where the polymeric films are exposed to high temperature conditions.
  • T g glass transition temperatures
  • the devices may be subjected to testing at 60° C. and 90% relative humidity (RH) or at 85° C. and 85% RH.
  • the T g of the polymeric films should be sufficiently high to withstand any high temperature post-processing steps that are used to fabricate the electronic devices into which they are incorporated. For example, if a layer of material, such as an inorganic barrier layer, is deposited over the polymeric film the polymeric film should be stable enough to withstand the maximum deposition temperature for the inorganic material.
  • inorganic barrier layers can be deposited over polymeric planarizing layers using plasma enhanced chemical vapor deposition (PECVD), which can require deposition temperatures of 80° C. or higher.
  • PECVD plasma enhanced chemical vapor deposition
  • the polymeric film should have a T g that is higher than the testing or processing temperatures.
  • the curable ink compositions can be formulated to provide cured polymers having a T g of 80° C. or greater. This includes embodiments of ink compositions that are formulated to provide cured polymers having a T g of 85° C. or greater, and further includes embodiments of the ink compositions that are formulated to provide cured polymers having a T g of 90° C. or greater. Because the T g of a polymeric material can be measured from the bulk cured polymer or from a polymeric film of the polymer, various embodiments of the ink compositions, the preceding Tg values may apply to the bulk cured polymer or the cured polymeric film. For the purposes of this disclosure, T g measurements for the bulk cured polymers can be performed via Thermomechanical Analysis [TMA], as described in greater detail in the examples.
  • TMA Thermomechanical Analysis
  • Some embodiments of the curable ink compositions include a di(meth)acrylate monomer, such as an alkyl di(meth)acrylate monomer, where the generalized structure of an alkyl di(meth)acrylate is given by:
  • the alkyl chain of an alkyl di(meth)acrylate monomer can have between 3 to 21 carbon atoms and in various compositions, moreover between 3 to 14 carbon atoms.
  • Various embodiments of curable ink compositions of the present teachings can utilize an alkyl di(meth)acrylate monomer that can have an alkyl chain with between 6 to 12 carbon atoms.
  • factors that can guide the selection of an alkyl di(meth)acrylate monomer can include the resulting viscosity of a formulation at a selected deposition temperature, as well as falling within the range of a target surface tension.
  • An exemplary alkyl di(meth)acrylate monomer according to the present teachings is 1, 12 dodecanediol dimethacrylate, having the structure as shown below:
  • curable ink compositions of the present teachings can include between about 57 mol. % to about 97 mol. % of an alkyl di(meth)acrylate monomer, such as 1, 12 dodecanediol dimethacrylate (DDMA) monomer, further can include curable ink compositions that comprise about 71 mol. % to 93 mol. % of an alkyl di(meth)acrylate monomer, and still further can include curable ink compositions that comprise about 75 mol. % to 89 mol. % of an alkyl di(meth)acrylate monomer.
  • an alkyl di(meth)acrylate monomer such as 1, 12 dodecanediol dimethacrylate (DDMA) monomer
  • curable ink compositions that comprise about 71 mol. % to 93 mol. % of an alkyl di(meth)acrylate monomer
  • curable ink compositions that comprise about 75 mol. % to 89
  • the curable ink compositions of the present teachings can have a diurethane di(meth)acrylate monomer component in the in the formulation.
  • a generalized diurethane di(meth)acrylate monomer structure is given by:
  • urethane di(meth)acrylate monomers include diurethane dimethacrylates (DUDMA) and urethane dimethacylate, having the generalized structures shown below:
  • DMDMA diurethane dimethacrylates
  • urethane dimethacylate having the generalized structures shown below:
  • DUDMA can be a mixture of isomers in which R can be hydrogen (H) or methyl (CH 3 ) in essentially equal proportion.
  • the concentration of the DUDMA can be between about 1 mol. % to about 20 mol. %. This includes embodiments of the curable ink compositions having a DUDMA concentration in the range from 10 mol. % to 14 mol. %.
  • the curable ink compositions include monofunctional (meth)acrylates, such as an alkyl monoacrylates and/or alkyl monomethacrylate.
  • monofunctional (meth)acrylates such as an alkyl monoacrylates and/or alkyl monomethacrylate.
  • the use of monofunctional (meth)acrylates in the ink compositions can reduce the viscosity of the ink compositions and may also provide the cured polymeric films formed from the ink compositions with a lower elastic modulus and, therefore, a higher flexibility.
  • Examples of mono(meth)acrylates include long alkyl chain (C8-C12) (meth)acrylates, such as lauryl (meth)acrylate (C12), decyl (meth)acrylate (C10) and octyl (meth)acrylate (C8), and shorter alkyl chain (C4-C6) (meth)acrylates.
  • longer chain (meth)acrylates such as stearyl (meth)acrylate
  • Other examples include di(ethylene glycol) methyl ether (meth)acrylate (DEGME(M)A), diethylene glycol monoethyl ether acrylate, and ethylene glycol methyl ether (meth)acrylate (EGME(M)A).
  • Still other suitable (meth)acrylate monomers include, but are not limited to: alkyl (meth)acrylates, such as methyl (meth)acrylate and ethyl (meth)acrylate; cyclic (meth)acrylates, such as tetrahydrofurfuryl methacrylate, alkoxylated tetrahydrofurfuryl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate; and aromatic (meth)acrylates, such as benzyl (meth)acrylate and phenoxyalkyl (meth)acrylates, including 2-phenoxyethyl (meth)acrylate and phenoxymethyl (meth)acrylate.
  • alkyl (meth)acrylates such as methyl (meth)acrylate and ethyl (meth)acrylate
  • cyclic (meth)acrylates such as tetrahydrofurfuryl methacrylate, alkoxylated tetrahydrofurfur
  • multifunctional crosslinking agents can be included in the curable ink compositions of the present teachings.
  • the term multifunctional crosslinking agent refers to a crosslinking agent having at least three reactive crosslinkable groups.
  • multifunctional (meth)acrylate crosslinking agents can be, for example, tri(meth)acrylates, tetra(meth)acrylates, as well as higher functionality (meth)acrylates.
  • curable ink compositions of the present teachings can include trimethylolpropane tri(meth)acrylate or pentaerythritol tetra(meth)acrylate, as well as combinations thereof.
  • tetrafunctional and higher functionality (meth)acrylates is advantageous for applications where a high T g polymer film is desired because the tetra- and higher-functionality (meth)acrylates increase the T g of the polymer film, relative to a polymer film made from an ink composition without the tetra- and higher-functionality (meth)acrylates.
  • curable ink compositions of the present teachings can include multifunctional crosslinking agents at concentration in the range from, for example, 1 mol. % to 15 mol. %.
  • concentrations outside of these ranges can be used.
  • each multifunctional crosslinking agent can have a concentration falling within the above-references ranges.
  • an ink composition can include a trimethylolpropane tri(meth)acrylate at a concentration in a range of between about 1-15 mol. %.
  • a pentaerythritol tetra(meth)acrylate monomer can be included at a concentration in a range of between about 1-15 mol. % of a composition.
  • trimethylolpropane tri(meth)acrylate for various embodiments of a curable ink composition of the present teachings is trimethylolpropane triacrylate, the structure of which is given below:
  • pentaerythritol tetra(meth)acrylate is shown below:
  • Suitable cure initiators include photoinitiators (PIs), thermal initiators, and initiators that induce polymerization using other types of energy, such as electron beam initiators.
  • photoinitiators are used.
  • the initiators may be present in amounts in the range from about 1 mol. % to about 10 mol. %. This includes embodiments in which the initiators are present in amounts in the range from about 2 mol. % to about 6 mol. %. However, amounts outside of these ranges can also be used.
  • the photoinitiator may be a Type I or a Type II photoinitiator.
  • Type I photoinitiators undergo radiation-induced cleavage to generate two free radicals, one of which is reactive and initiates polymerization.
  • photoinitiator fragments may be present in the cured polymeric films made from the ink compositions.
  • Type II photoinitiators undergo a radiation-induced conversion into an excited triplet state. The molecules in the excited triplet state then react with molecules in the ground state to produce polymerization initiating radicals.
  • the photoinitiator may be present in the cured polymeric films made from the ink compositions.
  • the specific photoinitiators used for a given curable ink composition are desirably selected such that they are activated at wavelengths that are not damaging to the OLED materials.
  • various embodiments of the curable ink compositions include photoinitiators that have a primary absorbance with a peak in the range from about 365 nm to about 420 nm.
  • the light source used to activate the photoinitiators and induce the curing of the curable ink compositions is desirably selected such that the absorbance range of the photoinitiator matches or overlaps with the output of the light source, whereby absorption of the light creates free radicals that initiate polymerization.
  • Suitable light sources may include mercury arc lamps and light emitting diodes.
  • An acylphosphine oxide photoinitiator can be used, though it is to be understood that a wide variety of photoinitiators can be used. For example, but not limited by, photoinitiators from the ⁇ -hydroxyketone, phenylglyoxylate, and ⁇ -aminoketone classes of photoinitiators can also be considered. For initiating a free-radical based polymerization, various classes of photoinitiators can have an absorption profile of between about 200 nm to about 400 nm.
  • an acylphosphine oxide photoinitiator can be about 0.1-5 mol. % of a formulation.
  • acylphosphine photoinitiators include Omnirad® TPO (also previously available under the tradename Lucirin® TPO) initiators for curing with optical energy in the wavelength range of about 365 nm to about 420 nm sold under the tradenames Omnirad® TPO, a type I hemolytic initiator which; with absorption @ 380 nm; Omnirad® TPO-L, a type I photoinitiator that absorbs at 380 nm; and Omnirad® 819 with absorption at 370 nm.
  • Omnirad® TPO also previously available under the tradename Lucirin® TPO
  • Omnirad® TPO a type I hemolytic initiator which; with absorption @ 380 nm
  • Omnirad® TPO-L a type I photoinitiator that absorbs at 380 nm
  • Omnirad® 819 with absorption at 370 nm.
  • a light source emitting at a nominal wavelength in the range from 350 nm to 395 nm at a radiant energy density of up to 2.0 J/cm 2 could be used to cure a curable ink composition comprising a TPO photoinitiator.
  • high levels of curing can be achieved.
  • some embodiments of the cured films have a degree of curing of 90% or greater, as measured by Fourier Transform Infrared (FTIR) spectroscopy.
  • FTIR Fourier Transform Infrared
  • Table 1 and Table 2 shown below summarize various components, as well as ranges for the components, for two non-limiting exemplary organic polymer compositions of the present teachings.
  • composition for Formulation I including component ranges Mol. % Component (Range) 1,12 Dodecanediol Dimethacrylate (DDMA) 57-97 Diurethane Dimethacrylate (DUDMA) 1-20 Trimethylolpropane Triacrylate (TMPTA) 1-13 Ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (TPO) 1-10 Total
  • curable ink compositions of the present teachings are formulated to provide stability during processing of the formation of a complete encapsulation stack fabricated upon an OLED device, as well as long-term stability for the effective sealing of the device over its useful lifetime. Additionally, curable ink compositions of the present teachings are formulated to provide function, such as flexibility, and optical properties, such as to enhance the use of an OLED device. For example, in Formulation I, and Formulation II of an alkyl di(meth)acrylate monomer, such as DDMA, in conjunction with a selection of cross-linking agents, such as PET and TMPTA, can provide an organic planarizing layer with a hydrophobic property and high cross-linking density.
  • an alkyl di(meth)acrylate monomer such as DDMA
  • cross-linking agents such as PET and TMPTA
  • DUDMA diurethane di(meth)acrylate monomer
  • a mixture of trifunctional and tetra-functional crosslinking agents can be used to provide for mechanical strength and desired degree of polymer crosslinking, and at the same time render sufficient segment mobility within the polymer network to provide for targeted polymer film flexibility.
  • the surface tension, viscosity and wetting properties of the curable ink compositions should be tailored to allow the compositions to be dispensed through an inkjet printing nozzle without drying onto or clogging the nozzle at the temperature used for printing (e.g., room temperature; ca. 25° C.).
  • various embodiments of the curable ink compositions can have a viscosity of between about 10 cP and about 28 cP (including, for example, between about 15 cP and about 26 cP) at 25° C.
  • FIG. 2 illustrates generally a graph of viscosity as a function of temperature for Formulation I
  • FIG. 3 illustrates generally a graph of viscosity as a function of temperature for Formulation II
  • Jetting temperatures can be between about 20° C. to about 50° C., including temperatures between 22° C. to about 40° C.
  • various embodiments of organic polymer formulations can have a viscosity of between about 7-25 cP; including, for example, between about 9 cP and about 19 cP.
  • curable ink compositions can be prepared to prevent exposure to light.
  • the compositions in order to ensure the stability of various compositions, can be prepared in a dark or very dimly lit room or in a facility in which the lighting is controlled to exclude wavelengths that would induce polymerization. Such wavelengths generally include those below about 500 nm.
  • the lid of a clean amber vial for example, Falcons, VWR trace clean
  • the lid of a clean amber vial for example, Falcons, VWR trace clean
  • a desired amount of a photoinitiator can be weighed into the vial.
  • the di(meth)acrylate can be weighed into the vial.
  • the mono(meth)acrylate monomer can be weighed into the vial.
  • the crosslinking agent can be weighed into the vial.
  • a Teflon® coated magnetic stir bar can be inserted into the vial and the cap of vial secured. The solution can then be stirred, for example, for 30 minutes at temperatures in the range from room temperature to 50° C. and 600-1000 rpm.
  • the curable ink compositions can be dehydrated by mixing in the presence of a 10 wt. % 3A molecular sieve beads for a period of several hours or more to yield ⁇ 100 ppm moisture and then stored under a dry atmosphere, such as a compressed dry air atmosphere. Thereafter, the curable ink composition can be filtered, for example, through a 0.1 ⁇ m or 0.45 ⁇ m PTFE syringe filter or vacuum or pressure filter, followed by sonication for 30 minutes at ambient temperature to remove residual gases. The curable ink composition is then ready for use and should be stored away in a dark cool environment.
  • an organic thin film organic polymer preparation as described can have a viscosity of between about 10 cps and about 30 cP at 25° C. and a surface tension of between about 30 dynes/cm and about 40 dynes/cm at 25° C.
  • the curable ink compositions can be stable for long periods of time, as determined by the lack of precipitation or gelation under visual inspection and the stabilities in their room temperature viscosities and surface tensions. No significant changes were recorded in viscosity and surface tension of the curable ink compositions of Formulations I and II; any changes are deemed to be within measurement errors for at least 160 days at room temperature under compressed dry air atmosphere in the dark.
  • TMA Thermal Mechanical Analysis
  • film shrinkage is evaluated using a UV rheometer designed to follow the curing progress from onset of irradiation of the sample to a fully cured state, and the degree of curing is determined using FTIR analysis.
  • shrinkage of less than about 12% and degree of curing of between about 85%-90% are target values for those properties.
  • Optical properties of films formed from curable ink composition of the present teachings for various OLED devices include haze, percent optical transmission through a desired wavelength range, and color.
  • haze is a measure of the fraction of transmitted wide angle scattered light from a source that is transmitted through a film
  • a low percent haze is desirable for a polymeric planarizing layer.
  • a target for haze not to exceed 0.10% is clearly met by films formed from Formulation I and Formulation II.
  • the percent transmission of light in a wavelength range of between about 350 nm to about 750 nm for films formed from Formulation I and Formulation II is comparable to that of a glass reference.
  • a controlled process environment of the present teachings can include a process environment that is non-reactive to materials that are used in the fabrication of, for example, various OLED devices, as well as being a substantially low-particle process environment. Patterned printing of an organic thin film on an OLED device substrate in such a controlled environment can provide for high-volume, high yield processes for a variety of OLED devices, such as OLED display and lighting devices.
  • Curable ink compositions of the present teachings can be printed using a printing system, such as described in U.S. Pat. No. 9,343,678, issued May 17, 2016, which is incorporated herein in its entirety.
  • Various embodiments of the present organic polymer compositions can be inkjet printed into thin films that are continuous and have well-defined edges on such substrates as glass, plastics, silicon, and silicon nitride.
  • the organic polymer compositions can be used to print thin films having thicknesses in the range from about 2 ⁇ m to about 10 ⁇ m, or thicker, including thin films having thicknesses in the range from about 2 ⁇ m to about 8 ⁇ m. These thin films can be achieved with film thickness variation of, for example, 5% or lower.
  • Gas enclosure system 500 of FIG. 5 can include gas enclosure 1000 for housing printing system 2000 .
  • Printing system 2000 can be supported by printing system base 2150 , which can be a granite stage.
  • Printing system base 2150 can support a substrate support apparatus, such as a chuck, for example, but not limited by, a vacuum chuck, a substrate floatation chuck having pressure ports, and a substrate floatation chuck having vacuum and pressure ports.
  • a substrate support apparatus can be a substrate floatation table, such as substrate floatation table 2250 .
  • Substrate floatation table 2250 can be used to float a substrate during frictionless transport of the substrate.
  • printing system 2000 can have a Y-axis motion system utilizing air bushings.
  • FIG. 5 illustrates generally an example of gas enclosure system 500 of manufacturing system 3000 A configured with external gas loop 3200 for integrating and controlling gas sources, such as a source of CDA and a source of a non-reactive gas such as can be used to establish a controlled process environment for various enclosed manufacturing systems of the present teachings, as well as providing a source of gas for operating various pneumatically controlled devices.
  • a non-reactive gas can be any gas that does not undergo a chemical reaction with materials used in the manufacture of OLED devices, such as display and lighting devices, under process conditions.
  • a non-reactive gas can be a non-oxidizing gas.
  • blower loop 3280 can provide pressurized gas and at least partial vacuum for use with a floatation table 2250 .
  • gas enclosure system 500 can be generally configured so that a pressure of gas inside the gas enclosure 1000 can be maintained within a desired or specified range, such as using a valve coupled to a pressure monitor, P.
  • Gas enclosure system 500 can also be configured with various embodiments of a gas purification system that can be configured for purifying various reactive species from a non-reactive process gas.
  • a gas purification system according to the present teachings can maintain levels for each species of various reactive species, such as water vapor, oxygen, ozone, as well as organic solvent vapors, for example, at 100 ppm or lower, at 10 ppm or lower, at 1.0 ppm or lower, or at 0.1 ppm or lower.
  • Gas enclosure system 500 can also be configured with various embodiments of a circulation and filtration system for maintaining a substantially particle free environment.
  • a particle filtration system can maintain a low particle environment within a gas enclosure meeting the standards of International Standards Organization Standard (ISO) 14644-1:1999, “Cleanrooms and associated controlled environments—Part 1: Classification of air cleanliness,” as specified by Class 1 through Class 5.
  • ISO International Standards Organization Standard
  • Blower loop 3280 can include blower housing 3282 , which can enclose first blower 3284 for supplying a pressurized source of gas to substrate floatation table 2250 via line 3286 , and second blower 3290 , acting as a vacuum source for substrate floatation table 2250 via line 3292 , providing at least partial vacuum to substrate floatation table 2250 .
  • blower loop 3280 can be, configured with heat exchanger 3288 for maintaining gas from blower loop 3280 to substrate floatation table 2250 at a defined temperature.
  • non-reactive gas source 3201 can be in flow communication with low consumption manifold line 3212 via non-reactive gas line 3210 .
  • Low consumption manifold line 3212 is shown in flow communication with low consumption manifold 3215 .
  • Cross-line 3214 extends from a first flow juncture 3216 , which is located at the intersection of non-reactive gas line 3210 , low consumption manifold line 3212 , and cross-line 3214 .
  • Cross-line 3214 extends to a second flow juncture 3226 .
  • CDA line 3222 extends from a CDA source 3203 and continues as high consumption manifold line 3224 , which is in fluid communication with high consumption manifold 3225 .
  • CDA can be used during, for example, maintenance procedures.
  • non-reactive gas source 3201 can be in flow communication with low consumption manifold 3215 and high consumption manifold 3225 .
  • non-reactive gas source can be routed through external gas loop 3200 to provide non-reactive gas to gas enclosure 1000 , as well as providing non-reactive gas for operating various pneumatically operated apparatuses and devices used during the operation of printing system 2000 .
  • high consumption manifold 3225 can provide non-reactive gas from gas source 3201 during processing for the operation of various components for printing system 2000 housed in gas enclosure 1000 , such as, but not limited by, one or more of a pneumatic robot, a substrate floatation table, an air bearing, an air bushing, a compressed gas tool, a pneumatic actuator, and combinations thereof.
  • second flow juncture 3226 is positioned at the intersection of a cross-line 3214 , clean dry air line 3222 , and high consumption manifold line 3224 , which is in flow communication with high consumption manifold 3225 .
  • Cross-line 3214 extends from a first flow juncture 3216 , which is in flow communication with non-reactive gas line 3210 , which flow communication can be controlled by valve 3208 .
  • valve 3208 can be closed to prevent flow communication between non-reactive gas source 3201 and high consumption manifold 3225 , while valve 3206 can be opened thereby allowing flow communication between CDA source 3203 and high consumption manifold 3225 . Under such conditions, various components that are high consumption can be supplied CDA during maintenance.
  • such regulation can assist in maintaining a slight positive internal pressure of a gas enclosure system, which can be between about 2-12 mbar above the pressure in the environment external a gas enclosure. Maintaining the internal pressure of a gas enclosure at a desired slightly positive pressure versus an external pressure is necessary given that pressurized gas is also contemporaneously introduced into the gas enclosure system.
  • Variable demand of various devices and apparatuses can create an irregular pressure profile for various gas enclosure assemblies and systems of the present teachings.
  • the internal pressure of a gas enclosure can be maintained within a desired or specified range, by using a control system configured with a valve coupled to a pressure monitor, P, where the valve allows gas to be exhausted to another enclosure, system, or a region surrounding the gas enclosure 1000 using information obtained from the pressure monitor. Exhausted gas can be recovered and re-processed through gas circulation and purification systems as previously described herein.
  • FIG. 6 illustrates generally an isometric view of a manufacturing system 3000 B, such as including a first printing system 2000 A, a second printing system 2000 B and first curing system 1300 A and second curing system 1300 B as well other enclosed modules, that can be used in manufacturing various optoelectronic devices (e.g., an organic light emitting diode (OLED) device).
  • First and second curing systems 1300 A and 1300 B of the present teachings can be used for one or more of holding a substrate (e.g., to facilitate flowing or dispersing the deposited material layer, such as to achieve a more planar or uniform film), as well as curing (e.g.
  • a layer of material such as deposited by one or more of the first or second printing systems 2000 A and 2000 B.
  • a material layer that flows or disperses, or is cured, using the first and second processing systems 1300 A and 1300 B can include a portion of an encapsulation stack (such as a thin film layer comprising an organic thin film material that can cured or treated via exposure to optical energy).
  • the first or second processing systems 1300 A or 1300 B can be configured for holding substrates, such as in a stacked configuration.
  • the first and second printers 2000 A and 2000 B can be used, for example, to deposit the same layers on a substrate or printers 2000 A and 2000 B can be used to deposit different layers on a substrate.
  • Manufacturing system 3000 B can include an input or output module 1101 (e.g., a “loading module”), such as can be used as a load-lock or otherwise in a manner that allows transfer of a substrate into or out of an interior of one or more chambers of manufacturing system 3000 B in a manner that substantially avoids disruption of a controlled environment maintained within one or more enclosures of manufacturing system 3000 B.
  • a loading module e.g., a “loading module”
  • substantially avoids disruption can refer to avoiding raising a concentration of a reactive species by a specified amount, such as avoiding raising such a species by more than 10 parts per million, 100 parts per million, or 1000 parts per million within the one or more enclosures during or after a transfer operation of a substrate into or out the one or more enclosures.
  • a transfer module such as can include a handler, can be used to manipulate a substrate before, during, or after various operations.
  • a gas enclosure system can be referred to as a “gas enclosure system” and such enclosure assemblies can be constructed in a contoured fashion that reduces or minimizes an internal volume of a gas enclosure assembly, and at the same time provides a working volume for accommodating various footprints of a manufacturing system of the present teachings, such as the deposition (e.g., printing), holding, loading, curing systems or modules described herein.
  • a contoured gas enclosure assembly according to the present teachings can have a gas enclosure volume of between about 6 m 3 to about 95 m 3 for various examples of a gas enclosure assembly of the present teachings covering, for example, substrate sizes from Gen 3.5 to Gen 10.
  • a contoured gas enclosure assembly can have a gas enclosure volume of, for example, but not limited by, of between about 15 m 3 to about 30 m 3 , which might be useful for printing of, for example, Gen 5.5 to Gen 8.5 substrate sizes above, or other substrate sizes that can readily be derived therefrom.
  • FIG. 7 depicts flow diagram 100 that illustrates generally a process for the fabrication of an organic thin films on various device substrates.
  • FIG. 7 illustrates techniques, such as methods, that can include forming an organic thin-film planarizing layer over the active area a light emitting device (e.g., an of a OLED lighting or display device) formed on a substrate, such as for providing a mura-free organic thin film layer.
  • a substrate can be transferred onto a substrate support system of an enclosed printing system configured to provide a controlled process environment as previously described herein.
  • a substrate can be transferred to an enclosed printing system from, for example, an inorganic thin film encapsulation system.
  • a substrate support system can be configured to provide uniform support of the substrate at least in one or more active regions of the substrate.
  • a substrate support system can include a floatation table configuration, such as having various floatation control zones including one or more of a pneumatically-supplied gas cushion, or a combination of pneumatic and at least partial vacuum supplied regions to provide a gas cushion supporting the substrate.
  • a curable ink composition can be printed over a target deposition region of a substrate.
  • the substrate can be transferred from an enclosed printing system to an enclosed curing system configured to provide a controlled process environment as previously described herein.
  • a curing system can provide an apparatus that can uniformly illuminate a substrate or portion or a substrate with optical energy in a wavelength range from about 365 nm to about 420 nm.
  • a curing system can have a substrate support system that can provide a pneumatically supplied gas cushion, or a combination of pneumatic and at least partial vacuum supplied regions to provide a gas cushion supporting the substrate uniformly in a manner that can suppress or inhibit mura formation during one or more of a holding operation or curing operation.
  • the substrate can be held for a specified duration after printing and before curing, such as before an optical curing process is initiated.
  • the liquid organic polymer layer can be cured, for example, using an optical treatment provided within an enclosed curing system, such as to provide a mura-free organic thin film encapsulation layer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Metallurgy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mechanical Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Plasma & Fusion (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Electroluminescent Light Sources (AREA)
  • Laminated Bodies (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
US15/955,303 2017-04-21 2018-04-17 Compositions and Techniques for Forming Organic Thin Films Abandoned US20180309089A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
TW107113054A TWI841527B (zh) 2017-04-21 2018-04-17 用於形成有機薄膜的組成物和技術
US15/955,303 US20180309089A1 (en) 2017-04-21 2018-04-17 Compositions and Techniques for Forming Organic Thin Films
US17/809,243 US11844234B2 (en) 2017-04-21 2022-06-27 Compositions and techniques for forming organic thin films
US18/497,917 US20240081096A1 (en) 2017-04-21 2023-10-30 Curable compositions and techniques for forming organic thin films

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762488401P 2017-04-21 2017-04-21
US201862653035P 2018-04-05 2018-04-05
US15/955,303 US20180309089A1 (en) 2017-04-21 2018-04-17 Compositions and Techniques for Forming Organic Thin Films

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US17/809,243 Continuation US11844234B2 (en) 2017-04-21 2022-06-27 Compositions and techniques for forming organic thin films

Publications (1)

Publication Number Publication Date
US20180309089A1 true US20180309089A1 (en) 2018-10-25

Family

ID=63854158

Family Applications (3)

Application Number Title Priority Date Filing Date
US15/955,303 Abandoned US20180309089A1 (en) 2017-04-21 2018-04-17 Compositions and Techniques for Forming Organic Thin Films
US17/809,243 Active US11844234B2 (en) 2017-04-21 2022-06-27 Compositions and techniques for forming organic thin films
US18/497,917 Pending US20240081096A1 (en) 2017-04-21 2023-10-30 Curable compositions and techniques for forming organic thin films

Family Applications After (2)

Application Number Title Priority Date Filing Date
US17/809,243 Active US11844234B2 (en) 2017-04-21 2022-06-27 Compositions and techniques for forming organic thin films
US18/497,917 Pending US20240081096A1 (en) 2017-04-21 2023-10-30 Curable compositions and techniques for forming organic thin films

Country Status (6)

Country Link
US (3) US20180309089A1 (zh)
EP (1) EP3613091A4 (zh)
JP (2) JP7144864B2 (zh)
KR (2) KR102607711B1 (zh)
CN (1) CN111788265B (zh)
WO (1) WO2018195066A2 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019203120A1 (ja) * 2018-04-20 2019-10-24 積水化学工業株式会社 有機ｅｌ表示素子用封止剤
US11793021B2 (en) 2019-11-22 2023-10-17 Samsung Display Co., Ltd. Method of fabricating display device

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4303924A (en) * 1978-12-26 1981-12-01 The Mead Corporation Jet drop printing process utilizing a radiation curable ink
US4680368A (en) * 1985-06-05 1987-07-14 Mitsubishi Rayon Company Limited Ultraviolet curable ink composition
US20050197419A1 (en) * 2004-03-03 2005-09-08 Graziano Louis C. Radiation curable aqueous binders for ink jet inks
US20080045618A1 (en) * 2006-06-27 2008-02-21 Nagvekar Devdatt S Low viscosity UV curable ink formulations
US20090324970A1 (en) * 2008-06-30 2009-12-31 Shigehide Ito Barrier laminate, gas barrier film, device and method for producing barrier laminate
US20110318595A1 (en) * 2009-03-30 2011-12-29 Evonik Roehm Gmbh Coating composition, (meth)acrylic polymer and monomer mixture for producing the (meth)acrylic polymer
US20120083569A1 (en) * 2009-06-10 2012-04-05 Kunststoff-Und Farben-Gesellschaft Mbh Polymerizable Compounds, Curable Compositions And Methods
US20140178675A1 (en) * 2012-12-20 2014-06-26 Kyoung Jin Ha Composition for encapsulation and encapsulated apparatus including the same
US20160329524A1 (en) * 2014-01-16 2016-11-10 Hunet Plus Organic electronic device and fabrication method thereof
US20170145231A1 (en) * 2014-05-13 2017-05-25 Sericol Limited Inks
US20180339500A1 (en) * 2015-12-22 2018-11-29 3M Innovative Properties Company Acrylic polyvinyl acetal graphic films

Family Cites Families (88)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07169567A (ja) 1993-12-16 1995-07-04 Idemitsu Kosan Co Ltd 有機ｅｌ素子
US5607789A (en) 1995-01-23 1997-03-04 Duracell Inc. Light transparent multilayer moisture barrier for electrochemical cell tester and cell employing same
DE19603746A1 (de) 1995-10-20 1997-04-24 Bosch Gmbh Robert Elektrolumineszierendes Schichtsystem
US5690722A (en) 1996-10-28 1997-11-25 Hewlett-Packard Company Use of tetrafluoropropanol as co-solvent in ink-jet ink vehicles
US5952778A (en) 1997-03-18 1999-09-14 International Business Machines Corporation Encapsulated organic light emitting device
JP3290375B2 (ja) 1997-05-12 2002-06-10 松下電器産業株式会社 有機電界発光素子
JP3747127B2 (ja) 1997-07-28 2006-02-22 キヤノン株式会社 カラーフィルタの製造方法及び表示装置の製造方法及び表示装置を備えた情報処理装置の製造方法
US6146225A (en) 1998-07-30 2000-11-14 Agilent Technologies, Inc. Transparent, flexible permeability barrier for organic electroluminescent devices
EP1524708A3 (en) 1998-12-16 2006-07-26 Battelle Memorial Institute Environmental barrier material and methods of making.
US6268695B1 (en) 1998-12-16 2001-07-31 Battelle Memorial Institute Environmental barrier material for organic light emitting device and method of making
IL145317A0 (en) 1999-04-28 2002-06-30 Du Pont Flexible organic electronic device with improved resistance to oxygen and moisture degradation
US20090191342A1 (en) 1999-10-25 2009-07-30 Vitex Systems, Inc. Method for edge sealing barrier films
US6866901B2 (en) 1999-10-25 2005-03-15 Vitex Systems, Inc. Method for edge sealing barrier films
US6413645B1 (en) 2000-04-20 2002-07-02 Battelle Memorial Institute Ultrabarrier substrates
US6623861B2 (en) 2001-04-16 2003-09-23 Battelle Memorial Institute Multilayer plastic substrates
US7198832B2 (en) 1999-10-25 2007-04-03 Vitex Systems, Inc. Method for edge sealing barrier films
US6492026B1 (en) 2000-04-20 2002-12-10 Battelle Memorial Institute Smoothing and barrier layers on high Tg substrates
US6550906B2 (en) 2001-01-02 2003-04-22 3M Innovative Properties Company Method and apparatus for inkjet printing using UV radiation curable ink
US6664137B2 (en) 2001-03-29 2003-12-16 Universal Display Corporation Methods and structures for reducing lateral diffusion through cooperative barrier layers
KR100413450B1 (ko) 2001-07-20 2003-12-31 엘지전자 주식회사 표시소자의 보호막 구조
US7074501B2 (en) 2001-08-20 2006-07-11 Nova-Plasma Inc. Coatings with low permeation of gases and vapors
US6597111B2 (en) 2001-11-27 2003-07-22 Universal Display Corporation Protected organic optoelectronic devices
US7307119B2 (en) 2002-08-01 2007-12-11 Electronics And Telecommunications Research Institute Thin film material using pentaerythritol acrylate for encapsulation of organic or polymeric light emitting device, and encapsulation method for LED using the same
US7012363B2 (en) 2002-01-10 2006-03-14 Universal Display Corporation OLEDs having increased external electroluminescence quantum efficiencies
US7109653B2 (en) 2002-01-15 2006-09-19 Seiko Epson Corporation Sealing structure with barrier membrane for electronic element, display device, electronic apparatus, and fabrication method for electronic element
KR100475849B1 (ko) 2002-04-17 2005-03-10 한국전자통신연구원 습식 공정에 의하여 형성된 엔캡슐레이션 박막을 갖춘유기 전기발광 소자 및 그 제조 방법
US20030203210A1 (en) 2002-04-30 2003-10-30 Vitex Systems, Inc. Barrier coatings and methods of making same
US6949389B2 (en) 2002-05-02 2005-09-27 Osram Opto Semiconductors Gmbh Encapsulation for organic light emitting diodes devices
GB0221894D0 (en) * 2002-09-20 2002-10-30 Avecia Ltd Compositions
CN1176565C (zh) 2002-11-25 2004-11-17 清华大学 一种有机电致发光器件的封装层及其制备方法和应用
US6945647B2 (en) 2002-12-20 2005-09-20 Eastman Kodak Company Method for increasing the diameter of an ink jet ink dot
US7297460B2 (en) * 2003-02-26 2007-11-20 Agfa-Gevaert Radiation curable ink compositions suitable for ink-jet printing
US7018713B2 (en) 2003-04-02 2006-03-28 3M Innovative Properties Company Flexible high-temperature ultrabarrier
US7510913B2 (en) 2003-04-11 2009-03-31 Vitex Systems, Inc. Method of making an encapsulated plasma sensitive device
KR101035850B1 (ko) 2003-11-17 2011-05-19 삼성전자주식회사 박막 형성용 프린팅 설비
US20050137282A1 (en) 2003-12-19 2005-06-23 Cagle Phillip C. Liquid vehicle systems for improving latex ink-jet ink frequency response
US20050238846A1 (en) 2004-03-10 2005-10-27 Fuji Photo Film Co., Ltd. Gas barrier laminate film, method for producing the same and image display device utilizing the film
US7279506B2 (en) 2004-05-05 2007-10-09 Xerox Corporation Ink jettable overprint compositions
JP4159525B2 (ja) * 2004-08-23 2008-10-01 株式会社石井表記 配向膜形成方法およびインクジェット式プリントヘッド噴出検査装置
US8342636B2 (en) 2004-08-23 2013-01-01 Kabushiki Kaisha Ishiihyoki Discharge rate control method for ink-jet printer, ink spread inspecting method, and oriented film forming method
KR100736531B1 (ko) * 2005-03-16 2007-07-06 주식회사 엘지화학 단차 조절이 가능한 잉크
US7687119B2 (en) 2005-04-04 2010-03-30 Henkel Ag & Co. Kgaa Radiation-curable desiccant-filled adhesive/sealant
US20060223937A1 (en) 2005-04-04 2006-10-05 Herr Donald E Radiation curable cycloaliphatic barrier sealants
CN100368490C (zh) 2005-07-28 2008-02-13 中国印钞造币总公司 Uv固化隐形荧光变频油墨
US7767498B2 (en) * 2005-08-25 2010-08-03 Vitex Systems, Inc. Encapsulated devices and method of making
US7621794B2 (en) 2005-11-09 2009-11-24 International Display Systems, Inc. Method of encapsulating an organic light-emitting device
US7955700B2 (en) 2006-03-29 2011-06-07 Fujifilm Corporation Gas-barrier laminate film and method for producing same, and image display device
JP2007277467A (ja) 2006-04-10 2007-10-25 Sony Chemical & Information Device Corp 硬化性樹脂組成物
US8039739B1 (en) 2006-05-05 2011-10-18 Nanosolar, Inc. Individually encapsulated solar cells and solar cell strings
JP5315629B2 (ja) * 2006-08-11 2013-10-16 Ｊｎｃ株式会社 光硬化性インクジェットインク
JP2008087163A (ja) 2006-09-29 2008-04-17 Fujifilm Corp ガスバリア性積層フィルム、およびそれを用いた画像表示素子
JP2008106165A (ja) * 2006-10-26 2008-05-08 Chisso Corp インクジェット用インクおよび当該インクにより得られる硬化膜
US8101288B2 (en) 2007-06-11 2012-01-24 Fujifilm Corporation Gas barrier film and organic device using the same
JP5296343B2 (ja) 2007-07-31 2013-09-25 住友化学株式会社 バリア層つき基板、表示素子および表示素子の製造方法
JP4932758B2 (ja) 2008-02-06 2012-05-16 富士フイルム株式会社 発光デバイス及びその製造方法
KR100934752B1 (ko) 2008-04-10 2009-12-30 주식회사 잉크테크 광전자 소자용 잉크 조성물
JP5320167B2 (ja) 2008-05-30 2013-10-23 富士フイルム株式会社 バリア性積層体、ガスバリアフィルム、デバイスおよび積層体の製造方法
US8899171B2 (en) 2008-06-13 2014-12-02 Kateeva, Inc. Gas enclosure assembly and system
JP5281964B2 (ja) 2008-06-26 2013-09-04 富士フイルム株式会社 バリア性積層体、ガスバリアフィルム、デバイスおよび積層体の製造方法
US20100055407A1 (en) 2008-09-04 2010-03-04 Xerox Corporation Ultra-Violet Curable Gellant Inks For Creating Tactile Text And Images For Packaging Applications
FR2936651B1 (fr) 2008-09-30 2011-04-08 Commissariat Energie Atomique Dispositif optoelectronique organique et son procede d'encapsulation.
JP5594147B2 (ja) 2008-12-05 2014-09-24 旭硝子株式会社 光硬化性組成物および表面に微細パターンを有する成形体の製造方法
US9337446B2 (en) 2008-12-22 2016-05-10 Samsung Display Co., Ltd. Encapsulated RGB OLEDs having enhanced optical output
US9184410B2 (en) 2008-12-22 2015-11-10 Samsung Display Co., Ltd. Encapsulated white OLEDs having enhanced optical output
WO2010083236A1 (en) 2009-01-14 2010-07-22 Dow Corning Corporation Flexible barrier film, method of forming same, and organic electronic device including same
JP2010198735A (ja) 2009-02-20 2010-09-09 Fujifilm Corp 光学部材及び該光学部材を備えた有機エレクトロルミネッセンス表示装置
US8329306B2 (en) 2009-03-03 2012-12-11 Fujifilm Corporation Barrier laminate, gas barrier film, and device using the same
US8342669B2 (en) 2009-09-18 2013-01-01 Xerox Corporation Reactive ink components and methods for forming images using reactive inks
US9379323B2 (en) 2010-04-12 2016-06-28 Merck Patent Gmbh Composition having improved performance
KR101913870B1 (ko) 2010-07-02 2018-10-31 쓰리엠 이노베이티브 프로퍼티즈 컴파니 배리어 조립체
WO2012054037A1 (en) 2010-10-21 2012-04-26 Hewlett-Packard Development Company, L.P. Controlling ink deposition during printing
KR101199064B1 (ko) 2011-01-21 2012-11-07 엘지이노텍 주식회사 광 변환 부재, 이를 포함하는 표시장치 및 이의 제조방법
US8851649B2 (en) * 2011-05-13 2014-10-07 Eckart Gmbh UV ink jet printing ink composition
KR101424346B1 (ko) 2011-11-18 2014-08-01 주식회사 엘지화학 유기전자장치 봉지용 광경화형 점접착 필름, 유기전자장치 및 그의 봉지 방법
TWI582202B (zh) 2011-11-18 2017-05-11 Ｌｇ化學股份有限公司 用於封裝有機電子裝置之光可硬化壓感性黏著膜、有機電子裝置及用於封裝有機電子裝置之方法
TWI477824B (zh) 2011-12-27 2015-03-21 Asahi Kasei E Materials Corp Optical substrate and light emitting device
JP5803746B2 (ja) 2012-03-02 2015-11-04 株式会社リコー 光重合性インクジェットインク、インクカートリッジ
US8771787B2 (en) 2012-05-17 2014-07-08 Xerox Corporation Ink for digital offset printing applications
KR102108867B1 (ko) * 2012-07-19 2020-05-12 바스프 코팅스 게엠베하 수분 제거층용 방사선 경화성 조성물, 및 이의 제조 방법
WO2014021941A1 (en) 2012-07-30 2014-02-06 Unipixel Displays, Inc. Ink formulations for flexographic printing of high-resolution conducting patterns
TWI610806B (zh) 2012-08-08 2018-01-11 ３Ｍ新設資產公司 障壁膜，製造該障壁膜之方法，及包含該障壁膜之物件
KR101847229B1 (ko) * 2013-09-27 2018-05-29 주식회사 엘지화학 도너 필름용 광경화성 수지 조성물 및 도너 필름
KR101802574B1 (ko) * 2014-03-28 2017-12-01 삼성에스디아이 주식회사 유기발광소자 봉지용 조성물 및 이로부터 제조된 유기발광소자 표시장치
KR101712700B1 (ko) 2014-06-12 2017-03-07 제일모직주식회사 유기발광소자 봉지용 조성물 및 이를 사용한 유기발광소자 표시장치
US9909022B2 (en) * 2014-07-25 2018-03-06 Kateeva, Inc. Organic thin film ink compositions and methods
WO2016096937A1 (en) 2014-12-18 2016-06-23 Rolic Ag Radiation curable composition comprising hydrophilic nanoparticles
CN107925010B (zh) * 2015-08-17 2020-11-06 3M创新有限公司 阻挡膜构造
EP3344712A4 (en) * 2015-08-31 2019-05-15 Kateeva, Inc. INK COMPOSITIONS FOR ORGANIC THIN FILM BASED ON DI AND MONO (METH) ACRYLATE

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4303924A (en) * 1978-12-26 1981-12-01 The Mead Corporation Jet drop printing process utilizing a radiation curable ink
US4680368A (en) * 1985-06-05 1987-07-14 Mitsubishi Rayon Company Limited Ultraviolet curable ink composition
US20050197419A1 (en) * 2004-03-03 2005-09-08 Graziano Louis C. Radiation curable aqueous binders for ink jet inks
US20080045618A1 (en) * 2006-06-27 2008-02-21 Nagvekar Devdatt S Low viscosity UV curable ink formulations
US20090324970A1 (en) * 2008-06-30 2009-12-31 Shigehide Ito Barrier laminate, gas barrier film, device and method for producing barrier laminate
US20110318595A1 (en) * 2009-03-30 2011-12-29 Evonik Roehm Gmbh Coating composition, (meth)acrylic polymer and monomer mixture for producing the (meth)acrylic polymer
US20120083569A1 (en) * 2009-06-10 2012-04-05 Kunststoff-Und Farben-Gesellschaft Mbh Polymerizable Compounds, Curable Compositions And Methods
US20140178675A1 (en) * 2012-12-20 2014-06-26 Kyoung Jin Ha Composition for encapsulation and encapsulated apparatus including the same
US20160329524A1 (en) * 2014-01-16 2016-11-10 Hunet Plus Organic electronic device and fabrication method thereof
US20170145231A1 (en) * 2014-05-13 2017-05-25 Sericol Limited Inks
US20180339500A1 (en) * 2015-12-22 2018-11-29 3M Innovative Properties Company Acrylic polyvinyl acetal graphic films

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019203120A1 (ja) * 2018-04-20 2019-10-24 積水化学工業株式会社 有機ｅｌ表示素子用封止剤
US11793021B2 (en) 2019-11-22 2023-10-17 Samsung Display Co., Ltd. Method of fabricating display device

Also Published As

Publication number Publication date
KR20230167139A (ko) 2023-12-07
US11844234B2 (en) 2023-12-12
KR102607711B1 (ko) 2023-11-28
KR20190141149A (ko) 2019-12-23
WO2018195066A3 (en) 2020-03-26
TW201839070A (zh) 2018-11-01
EP3613091A4 (en) 2021-08-04
EP3613091A2 (en) 2020-02-26
WO2018195066A2 (en) 2018-10-25
JP7144864B2 (ja) 2022-09-30
JP2020520043A (ja) 2020-07-02
CN111788265B (zh) 2024-04-23
US20220328788A1 (en) 2022-10-13
US20240081096A1 (en) 2024-03-07
CN111788265A (zh) 2020-10-16
JP2022191227A (ja) 2022-12-27

Similar Documents

Publication Publication Date Title
US20240081096A1 (en) Curable compositions and techniques for forming organic thin films
US10190018B2 (en) Di- and mono(meth)acrylate based organic thin film ink compositions
US9909022B2 (en) Organic thin film ink compositions and methods
JP5441406B2 (ja) カプセル化されたデバイスおよび製造方法
US20180026234A1 (en) Methods of forming a polymeric thin film layer on an organic light-emitting diode substrate
KR20190118156A (ko) 향상된 광 아웃커플링을 갖는 발광 소자를 위한 잉크젯 인쇄 시스템 및 기술
US11732074B2 (en) Compositions and techniques for forming organic thin films
US10533104B2 (en) Two-step process for forming cured polymeric films for electronic device encapsulation
TWI841527B (zh) 用於形成有機薄膜的組成物和技術
TW202417582A (zh) 用於形成有機薄膜的組成物和技術
US20170358775A1 (en) Highly Spreading Polyethylene Glycol Di(meth)acrylate-Based Organic Thin Film Ink Compositions
KR101860095B1 (ko) 플렉시블 oled용 자외선 경화형 조성물 및 이의 용도
CN114686122A (zh) 有机el元件用密封剂、密封膜、有机el元件及有机el元件的制造方法
TW201742897A (zh) 基於聚乙二醇二（甲基）丙烯酸酯之高度展開有機薄膜的油墨組成物

Legal Events

Date Code Title Description
AS Assignment

Owner name: KATEEVA, INC., CALIFORNIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ROGOJINA, ELENA;RAMO, TERESA A.;YUWONO, CITRA;AND OTHERS;SIGNING DATES FROM 20180425 TO 20180426;REEL/FRAME:045686/0574

AS Assignment

Owner name: KATEEVA, INC., CALIFORNIA

Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE SECOND INVENTOR LAST NAME PREVIOUSLY RECORDED AT REEL: 045686 FRAME: 0574. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT;ASSIGNORS:ROGOJINA, ELENA;RAMOS, TERESA A.;YUWONO, CITRA;AND OTHERS;SIGNING DATES FROM 20180425 TO 20180426;REEL/FRAME:045791/0782

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

AS Assignment

Owner name: EAST WEST BANK, CALIFORNIA

Free format text: SECURITY INTEREST;ASSIGNOR:KATEEVA, INC.;REEL/FRAME:048806/0639

Effective date: 20190402

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

AS Assignment

Owner name: KATEEVA, INC., CALIFORNIA

Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:EAST WEST BANK, A CALIFORNIA BANKING CORPORATION;REEL/FRAME:051664/0802

Effective date: 20200121

AS Assignment

Owner name: SINO XIN JI LIMITED, HONG KONG

Free format text: SECURITY AGREEMENT;ASSIGNOR:KATEEVA, INC.;REEL/FRAME:051682/0212

Effective date: 20200120

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE AFTER FINAL ACTION FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

STCV Information on status: appeal procedure

Free format text: NOTICE OF APPEAL FILED

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE AFTER FINAL ACTION FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE AFTER FINAL ACTION FORWARDED TO EXAMINER

AS Assignment

Owner name: SINO XIN JI LIMITED, HONG KONG

Free format text: SECURITY INTEREST;ASSIGNORS:KATEEVA, INC.;KATEEVA CAYMAN HOLDING, INC.;REEL/FRAME:059382/0053

Effective date: 20220307

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

AS Assignment

Owner name: HB SOLUTION CO., LTD., KOREA, REPUBLIC OF

Free format text: SECURITY INTEREST;ASSIGNOR:KATEEVA CAYMAN HOLDING, INC.;REEL/FRAME:059727/0111

Effective date: 20220414

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION