Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
  • C07C323/02—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C323/03—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
  • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
  • C07D327/04—Five-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
  • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
  • C07D327/06—Six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
  • C07D339/02—Five-membered rings
  • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
  • C07D339/08—Six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/22—Organic compounds
  • C11D7/34—Organic compounds containing sulfur
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
  • C11D7/5009—Organic solvents containing phosphorus, sulfur or silicon, e.g. dimethylsulfoxide
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5004—Organic solvents
  • C11D7/5018—Halogenated solvents
• • 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
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
  • C11D2111/10—Objects to be cleaned
  • C11D2111/14—Hard surfaces
  • C11D2111/16—Metals
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
  • C11D2111/10—Objects to be cleaned
  • C11D2111/14—Hard surfaces
  • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
  • Y02W30/00—Technologies for solid waste management
  • Y02W30/50—Reuse, recycling or recovery technologies
  • Y02W30/82—Recycling of waste of electrical or electronic equipment [WEEE]

Definitions

• the present disclosure relates to compositions and methods for removing electroluminescent materials from substrates.
• compositions for removing electroluminescent materials from metal substrates are described in, for example, U.S. Pat. 7,073,518.
• a composition includes a hydroflourothioether represented by the following structural formula (I):
• Rf-S-Rh (I) where Rf is a fluorinated or perfluorinated group having 2-9 carbon atoms and optionally includes one or more catenated heteroatoms or chlorine atoms, and Rh is a non-fluorinated hydrocarbon group having 1-3 carbon atoms.
• the composition further includes an electroluminescent material.
• organic light emitting diode OLED
• electroluminescent materials In the organic light emitting diode (OLED) manufacturing process, it is common for electroluminescent materials to be deposited onto (or otherwise present on) a metal mask. In order for these metal masks to be reused, the electroluminescent materials must be removed. Certain solvents, such as N-Methyl-2-pyrrolidone (NMP), N-2- butylpyrrolidone (NBP), cyclohexanone, or isopropyl alcohol (IP A), may be used to remove the electroluminescent materials from the metal masks.
• NMP N-Methyl-2-pyrrolidone
• NBP N-2-butylpyrrolidone
• IP A isopropyl alcohol
• the solvents must then be removed from the metal masks (e.g., rinsed off) using an additional solvent (e.g., hydrofluoroether fluids) because the drying time for such initial solvents is unacceptably long due to their high boiling points.
• an additional solvent e.g., hydrofluoroether fluids
• use of these solvents is undesirable, generally, due to their unfavorable environmental profiles (e.g., high GWPs), toxicity profiles, or flash points (i.e., safety concerns).
• compositions that facilitate single step electroluminescent material removal.
• the compositions are an azeotropic blend of a hydroflourocompound and an organic solvent (e.g., /ra//.s-dichloroethylene) that form an azeotrope.
• Such multi-component compositions are less than ideal because they include chlorine containing materials (e.g., Irans-d ⁇ chi oroethy 1 ene) for acceptable cleaning performance, which the industry prefers to avoid.
• compositions and methods for removing electroluminescent materials from metal masks that (i) can be carried out in a single step process (that is, a process that may not require an additional rinsing step) using a single component composition (as opposed to a blend); and/or (ii) employ materials with more favorable toxicity profiles and/or no flash points, may be desirable.
• compositions and methods for removing electroluminescent materials from metal masks including certain hydrofluorothioethers.
• these hydrofluorothioethers exhibit a unique combination of cleaning performance and accelerated drying time (i.e., enable a one-step process) while also providing favorable toxicity, non-flammability and environmental profiles.
• fluoro- for example, in reference to a group or moiety, such as in the case of "fluoroalkylene” or “fluoroalkyl” or “fluorocarbon" or “fluorinated” means partially fluorinated such that there is at least one carbon-bonded hydrogen atom
• perfluoro- for example, in reference to a group or moiety, such as in the case of "perfluoroalkylene” or “perfluoroalkyl” or “perfluorocarbon" or “perfluorinated” means completely fluorinated such that, except as may be otherwise indicated, there are no carbon-bonded hydrogen atoms replaceable with fluorine.
• the present disclosure is directed to compositions for removing electroluminescent materials from a substrate (e.g., a metal mask of the type commonly used in the OLED manufacturing process).
• the composition may include one or more hydrofluorothioether compounds.
• suitable hydrofluorothioethers are represented by the following structural formula (I):
• Rf is a partially fluorinated or perfluorinated group having 2 to 9, 2 to 6, 2 to 5, or 2 to 4 carbon atoms that is saturated or unsaturated, linear or branched, acyclic or cyclic, and optionally includes one or more catenated heteroatoms, chlorine atoms, or bromine atoms.
• Rf is partially fluorinated.
• Rf has no more than two hydrogen atoms.
• Rf is perfluorinated.
• Rf is a perfluorinated, saturated, branched group having 3 to 6 carbon atoms.
• Rh is a non-fluorinated hydrocarbon group having 1-3 or 1- 2 carbon atoms that is saturated or unsaturated, linear or branched, and optionally includes one or more catenated heteroatoms.
• Rh is CFf or CH 3 CH 2 .
• Rh is CFL.
• suitable hydrofluorothioethers are represented by the following structural formula (II):
• n is 0 or 1; x is an oxygen atom or sulfur atom; and (i) Rh’ is a partially fluorinated alkyl group having 1-4 or 1-3 carbon atoms and at least 1 hydrogen atom, and optionally includes one or more catenated heteroatoms, chlorine atoms, or bromine atoms; and Rf is a perfluoroalkyl group having 1-4 or 1-3 carbon atoms, and optionally includes one or more catenated heteroatoms, chlorine atoms, or bromine atoms; or (ii) Rh’ and Rf are bonded together to form a 5- or 6-membered fluorinated ring having at least one hydrogen atom and optionally including one or more catenated heteroatoms, chlorine atoms, or bromine atoms.
• any of the above discussed catenated heteroatoms may be secondary O heteroatoms wherein the O is bonded to two carbon atoms. In some embodiments, any of the above discussed catenated heteroatoms may be tertiary N heteroatoms wherein the N is bonded to three carbon atoms.
• the fluorine content in the hydrofluorothioether compounds of the present disclosure may be sufficient to make the compounds non-flammable according to ASTM D-3278-96 e-1 test method (“Flash Point of Liquids by Small Scale Closed Cup Apparatus”).
• representative examples of the compounds of general formula (I) include the following:
• the present disclosure is directed to a working fluid for removing electroluminescent materials from a substrate.
• the working fluids may include the above-described hydrofluorothioether compounds in an amount of at least 50 wt. %, at least 70 wt. %, at least 90 wt. %; at least 95 wt. %, or at least 99 wt. %, based on the total weight of the composition.
• the working fluids may consist essentially of the hydrofluorothioethers of the present disclosure.
• such working fluids may also include one or more additional solvents (e.g., NMP, NBP, cyclohexanone, or IP A).
• such additional solvents may be present in the working fluids, but may be present in an amount of less than 10 wt. %, less than 5 wt. %, or less than 1 wt. %, based on the total weight of the working fluid.
• compositions of the present disclosure have been discovered to adequately remove electroluminescent materials (e.g., OLED dyes) from the surface of metal substrates and are associated with significantly shorter drying times relative to the materials conventionally employed in metal mask cleaning processes (e.g, NMP, cyclohexanone, and IP A).
• electroluminescent materials e.g., OLED dyes
• the present disclosure is further directed to the above- described compositions, in their post-clean state.
• the present disclosure is directed to any of the above-described cleaning compositions that include one or more electroluminescent materials dissolved, dispersed, or otherwise contained therein.
• the electroluminescent materials may include any highly conjugated dye that responds to electric stimulation (such as those often employed in the OLED manufacturing process).
• the electroluminescent materials may include copper (II) phthalocyanine, iridium, or platinum.
• the electroluminescent materials may be present in the post-clean compositions in an amount of at least 0.001 wt. % or at least 0.01 wt. %., based on the total weight of post-clean composition.
• compositions of the present disclosure have favorable toxicity profiles. More specifically, the compositions of the present disclosure may toxicity profiles that are more favorable than those of materials commonly employed to clean electroluminescent materials from metal masks (e.g., NMP).
• the present disclosure is further directed to methods of cleaning metal substrates. More specifically, in some embodiments, the present disclosure is further directed to methods of removing electroluminescent materials from metal masks (such as those commonly used in the OLED manufacturing process).
• the method first includes providing a metallic substrate (e.g., a metal mask) having an electroluminescent material disposed on an external surface of the substrate.
• the electroluminescent material may be disposed on the external surface in a layer having a thickness of at least 10,000 Angstroms, at least 15,000 Angstroms, or at least 20,000 Angstroms.
• the method may then include contacting any of the above described hydrofluorothioethers or working fluids with the electroluminescent material carrying metal mask.
• the hydrofluorothioethers or working fluids can be used in either the gaseous or the liquid state (or both), and any of known or future techniques for “contacting” the substrate can be utilized.
• a liquid composition can be sprayed or brushed onto the substrate, a gaseous composition can be blown across the substrate, or the substrate can be immersed (partially or completely) in either a gaseous or liquid composition. Elevated temperatures, ultrasonic energy, and/or agitation can be used to facilitate the cleaning.
• the methods of the present disclosure are carried out at room temperature.
• the method may then include removing the hydrofluorothioethers or working fluids from the metal masks. Such removal may be carried out via simple evaporation as the hydrofluorothioethers of the present disclosure were found to easily evaporate leaving a clean and dry metal mask surface.
• the hydrofluorothioethers of the present disclosure may also be used in combination with one or more of the commonly employed solvents for removing electroluminescent materials from metal masks (e.g., NMP, NBP, cyclohexanone, or IP A).
• the method may include, first, contacting the electroluminescent material carrying metal mask with any one or more of the commonly employed solvents.
• the commonly employed solvents can be characterized as the primary mechanism for displacing the electroluminescent materials from the metal masks. It is to be appreciated that following displacement of the electroluminescent material, some amount of the solvent will remain on the metal mask.
• the methods of the present disclosure may then include removing the solvents by contacting the solvent carrying metal mask with any of the above described hydrofluorothioethers or working fluids.
• the hydrofluorothioethers of the present disclosure efficiently wet and displace the commonly employed solvents, and rapidly evaporate.
• the hydrofluorothioethers exhibit exceptional stability in the presence of the amine containing solvents (NMP and NBP). In this embodiment, such stability may be important in that instability would lead to fluoride generation which significantly reduces the efficacy of the fluorinated solvent for cleaning.
• the method may then include removing the hydrofluorothioethers or working fluids from the metal masks (e.g., via evaporation).
• the crude material was collected as a pale yellow oil (117g, 93% desired product by GC-fid). This material was purified by distillation at ambient pressure to give the perfluoroisopropyl methyl thioether (98g, 45% yield, b.p. 65 °C).
• Solubility of organic luminescent material in hydrofluoroether and comparative solvents Test mixtures were prepared by adding 0.01 g (grams) of one of the electroluminescent materials (ALQ3, or FIrPic) to 3 g of one of the fluids (NMP, NBP, CHO, NOVEC 73DE, or HFTE1). Each mixture was agitated for 5 minutes, and the resulting material was observed with the unaided eye for haziness and undissolved particulate matter. A qualitative solubility rating was assigned to each mixture as described in Table 2. Results are in Table 3. A solubility rating of 1 or 2 was interpreted to mean that the fluid would be useful for cleaning electroluminescent materials from substrates such as metal mesh.
• Boiling points of the single-component fluid solvents are summarized in Table 4.
• a relatively low boiling point is interpreted as an indication of a relatively lower drying time.
• the boiling point of HFTE1 is much lower than the boiling points of NMP, NBP, and CHO, indicating that HFTE1 will dry more quickly than the comparative compounds.

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• 2020
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