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WO2025123268A1 - Compositions de solvant eutectique profond pour applications électroniques - Google Patents

Compositions de solvant eutectique profond pour applications électroniques Download PDF

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Publication number
WO2025123268A1
WO2025123268A1 PCT/CN2023/138692 CN2023138692W WO2025123268A1 WO 2025123268 A1 WO2025123268 A1 WO 2025123268A1 CN 2023138692 W CN2023138692 W CN 2023138692W WO 2025123268 A1 WO2025123268 A1 WO 2025123268A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
urea
solvent
des
glycerine
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.)
Pending
Application number
PCT/CN2023/138692
Other languages
English (en)
Inventor
Qinyuan GUI
Cheng Shen
Hua Ren
Jongcheol Kim
Tsukishima SHIN
Jitao CHEN
Meijia HE
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.)
Dow Chemical Korea Ltd
Dow Global Technologies LLC
Original Assignee
Dow Chemical Korea Ltd
Dow Global Technologies LLC
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
Application filed by Dow Chemical Korea Ltd, Dow Global Technologies LLC filed Critical Dow Chemical Korea Ltd
Priority to PCT/CN2023/138692 priority Critical patent/WO2025123268A1/fr
Publication of WO2025123268A1 publication Critical patent/WO2025123268A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
    • C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain

Definitions

  • Embodiments relate to solvent compositions containing a mixture of two or more deep eutectic solvents and a glycol ether solvent for use in electronic and photolithography applications.
  • Photosensitive materials are used extensively, for example in the electronics industry in the fabrication of integrated circuits.
  • One useful class of photosensitive materials is the class of photosensitive polyimides (PSPI) .
  • PSPI photosensitive polyimides
  • Polyimides in general, are usually the reaction products of one or more dianhydride monomer with one or more diamine monomer.
  • one or more of the monomers has one or more substituent groups, such that the substituent group is capable of reacting with a photon to form a group that initiates a crosslinking reaction and/or is capable of participating in a crosslinking reaction.
  • a layer that contains a photosensitive polyimide or photoresist is present on a surface. Some portions of the layer are exposed to radiation (such as, for example, ultraviolet light) , while other portions are not. The portions exposed to radiation present different dissolving performance in developers compared with the unexposed portions.
  • the layer is then contacted with an alkaline solution, which degrades the non-crosslinked polyimide or photoresist to produce monomeric moieties; the layer is then washed with one or more solvents to dissolve the monomeric moieties; and then the layer is washed with water to remove the solvent along with the dissolved monomeric moieties.
  • Solvents suitable for dissolving photoresists or PSPI-forming monomers prioritize a number of factors, such as selecting solvents that are relatively non-volatile, have a melting point of 65°C or lower, non-halogenated, and low toxicity. While N-Methyl-2-Pyrrolidone (NMP) has been widely used to fill the role as solvent for photoresists or PSPI-forming monomers, the solvent has been identified as a threat to human reproductive health and alternatives are needed.
  • NMP N-Methyl-2-Pyrrolidone
  • embodiments disclosed herein are directed to methods that include dissolving one or more photosensitive polyimide-forming monomers with a solvent composition containing a mixture of: a deep eutectic solvent (DES) composition containing: urea, glycerine, and optionally betaine or triethanolamine; and a glycol ether according to the formula:
  • DES deep eutectic solvent
  • R1 is hydrogen or a C1 to C4 alkyl chain
  • R2 is hydrogen or methyl
  • n ranges from 1 to 4.
  • compositions consisting essentially of a DES composition containing: urea, glycerine, and optionally betaine or triethanolamine; and a glycol ether according to the formula:
  • R1 is hydrogen or a C1 to C4 alkyl chain
  • R2 is hydrogen or methyl
  • n ranges from 1 to 4
  • the solvent composition has a viscosity determined according to ASTM D445 of 80 cP or less.
  • Embodiments relate to solvent compositions containing a mixture of two or more deep eutectic solvents and a glycol ether solvent for use in electronic and photolithography applications.
  • Solvent compositions may include a DES composition and one or more glycol ether solvents to modify various properties including viscosity and solubilizing effectiveness for various highly polar materials, including PSPI-forming (co) monomers.
  • Solvent compositions may be used as a bio-friendly alternative to replace NMP for the application of electronic processing, such as dissolving monomers for PSPI synthesis, photoresist stripping, and the like.
  • Solvent compositions disclosed herein may meet the criteria for minimal toxicity, including safety in reproductive risk as outlined in the 2012 publication "Hazard Communication Standard, " published by the US Occupational Health and Safety Administration in US Federal Regulations publication 29 CFR 1910.1200.
  • Solvent compositions disclosed herein may be essentially free of halogen atoms.
  • the amount of halogen atoms present in the solvent composition may be present at a percent by weight (wt%) of less than 0.1 wt%, less than 0.01 wt%, or 0.001 wt%.
  • Solvent compositions may include mixtures containing a DES composition, one or more glycol ether solvents, and optionally one or more polyglycols.
  • the term “deep eutectic solvent” means a mixture of two or more materials that are capable of self-association, such as through hydrogen bond interactions, to form a eutectic mixture with a melting point lower than that of each individual component.
  • the DES composition may include two or more chemicals.
  • the DES composition may be a binary composition containing urea and glycerin; or a ternary composition containing betaine, urea, and glycerin, or triethanolamine, urea, and glycerine.
  • Binary DES compositions may include a mixture of urea and glycerine at a molar ratio ranging from 1 ⁇ 50 to 1 ⁇ 1, or 1 ⁇ 50 to 1 ⁇ 4.
  • the molar ratio of betaine ⁇ urea ⁇ glycerine may range from 0.11 ⁇ 0.44 ⁇ 0.44 to 0.16 ⁇ 0.33 ⁇ 0.5, or 0.28 ⁇ 0.14 ⁇ 0.57 to 0.16 ⁇ 0.33 ⁇ 0.5.
  • the molar ratio of triethanolamine ⁇ urea ⁇ glycerin may range from 0.01 ⁇ 0.03 ⁇ 0.95 to 0.95 ⁇ 0.03 ⁇ 0.01.
  • Solvent compositions may include one or more glycol ethers that are used to control viscosity and solubilization of PSPI monomers. Suitable glycol ethers may be described according to the formula:
  • Suitable glycol ethers may include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, tripropylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol n-propyl ether, propylene glycol t-butyl ether, propylene glycol n-butyl ether, dipropylene glycol methyl ether, dipropylene glycoln-propyl ether, dipropylene glycol t-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-propyl ether, tripropylene glycol t-butyl ether, tripropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, tripropylene glycol n-butyl ether
  • Solvent compositions may include a mass ratio of a DES composition and one or more glycol ethers ranging from 4 ⁇ 1 to 1 ⁇ 4, 3 ⁇ 1 to 1 ⁇ 4, or 2 ⁇ 1 to 1 ⁇ 4.
  • Solvent compositions may also include one or more polyglycols such as triethylene glycol and tetraethylene glycol. Solvent compositions may include a polyglycol at a percent by weight (wt%) of 80 wt%or less, 70 wt%or less, or 60 wt%or less, such as in a range of 1.5 wt%to 60 wt%.
  • wt% percent by weight
  • Solvent compositions containing mixtures of DES compositions, glycol ethers and optional polyglycol may have a viscosity determined according to ASTM D445 of 80 cP or less, 75 cP or less, or 60 cP or less, such as in a range of 15 cP to 80 cP.
  • Solvent compositions may have suitable properties for a number of electronic manufacturing applications, such as solubilizing PSPI (co) monomers for synthesis or removal, photoresist stripping, photolithography, and the like.
  • Methods may include dissolving one or more photosensitive polyimide-forming monomers with a solvent composition comprising a mixture of: a DES composition containing urea, glycerine, and optionally betaine or triethanolamine; and a glycol ether according to the formula:
  • R1 is hydrogen or a C1 to C4 alkyl chain
  • R2 is hydrogen or methyl
  • n ranges from 1 to 4.
  • Solvent compositions disclosed herein may be capable of solubilizing PSPI-forming monomers at percent by weight (wt%) of at least 0.5 wt%.
  • PSPI monomers include dianhydrides including bisphenol-A dianhydride, oxydiphthalic anhydride such as 4, 4’-Oxydiphthalic anhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, pyromellitic dianhydride, and mixtures thereof; and diamines such as meta-phenylenediamine, para-phenylenediamine, oxydianiline, diaminodiphenylsulfone, 1, 3-bis (3-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 4, 4′-bis (3-aminophenoxy) biphenyl, 4, 4′-bis (4-aminophenoxy) biphenyl, bis (aminophen
  • Methods may also include photoresist stripping and photolithography processes that include providing a surface having a photoresist layer; and stripping at least a portion of the photoresist layer from the surface with the solvent mixture of the present disclosure.
  • Photoresist layers may be selected from those formed by a photosensitive polyimide layer, a phenolic resin layer, an acrylic layer or combination thereof.
  • formulation components and properties have been disclosed individually, it is envisioned that component elements may be included, excluded, or combined in any manner or subcombination utilizing any of the above concentration ranges and nested subranges therein. Further, that the recited formulation properties may be similarly achieved through various combinations of the recited components within the recited ranges.
  • CE1 is selected as NMP and CE2 is CARBITOL TM Solvent.
  • CEs and IEs they are the combination of DES and glycol ether solvent.
  • the DES is formulated by combining different ratio of betaine, urea and glycerin. The formulations are summarized in Tables 2 and 3.
  • the DES was prepared with heating and stirring methods. Specifically, the designed amount of betaine, urea, and glycerin were put into a glass beaker and heated to 80 °C with continuous stirring at 300 rpm. After 2 hours of stirring, a transparent DES was obtained. The DES composition was then cooled to room temperature. Solvent samples were prepared by combining the DES composition with the desired amount of glycol ether solvent, and left at room temperature until any generated bubbles disappeared.
  • glycol ether solvent in IE1 to IE7 improves photoresist stripping performance.
  • the higher concentration of glycol ether solvent possesses better performance to photoresist stripping, which is attributed to a reduction in viscosity and enhanced penetration and stripping performance.
  • samples containing betaine or TEA exhibit increased monomer dissolution properties. Similar results are demonstrated for glycerin. Compared with glycol ether alone, the combination of DES has a significant increase in monomer dissolving performance.
  • Viscosity measurements were conducted on a Hamilton Microlab Star (Hamilton Robotics, Inc. ) under room temperature (22 °C) .
  • This is a kind of high throughput liquid handlers with 8 independent channels that uses air displacement to aspirate and dispense fluids and differential pressure sensors to continuously monitor the pressure inside the pipet tips.
  • 1.00 gram of each solvent mixture was transferred into a glass vial and placed in 96-well plates. The samples were then sent for testing on Hamilton Microlab Star. After 20 minutes of testing, the results can be read on the screen. Viscosity testing results are shown in Tables 8 and 9.
  • inventive samples IE1 to IE7 containing DES and glycol ether solvent form a complementary system in which the DES composition functions as a high polar solvent, while the glycol ether solvent reduces the viscosity of the mixture without affecting polarity or solubilizing performance.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des procédés qui comprennent la dissolution d'un ou de plusieurs monomères photosensibles formant un polyimide avec une composition de solvant contenant un mélange de : une composition de solvant eutectique profond (DES) contenant : de l'urée, de la glycérine, et éventuellement de la bétaïne ou de la triéthanolamine; et un éther de glycol selon la formule (I). Dans la mesure où R1 représente un atome d'hydrogène ou une chaîne alkyle en C1 à C4, R2 représente un atome d'hydrogène ou un groupe méthyle, n est compris entre 1 et 4. Les compositions peuvent consister essentiellement en une composition de solvant eutectique profond (DES) contenant : de l'urée, de la glycérine et éventuellement de la bétaïne ou de la triéthanolamine; et un éther de glycol.
PCT/CN2023/138692 2023-12-14 2023-12-14 Compositions de solvant eutectique profond pour applications électroniques Pending WO2025123268A1 (fr)

Priority Applications (1)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0532953A2 (fr) * 1991-08-28 1993-03-24 Unitika Ltd. Solution de précurseur de polyimide, son procédé de préparation, masses à mouler et revêtement obtenus à partir de cette solution
WO2007047365A2 (fr) * 2005-10-13 2007-04-26 Advanced Technology Materials, Inc. Composition d'enlevement de photoresine et/ou de revetement antireflet sacrificiel, compatible avec les metaux
JP2019203120A (ja) * 2018-05-16 2019-11-28 旭化成株式会社 ポリイミド前駆体樹脂組成物
US20210088903A1 (en) * 2019-01-23 2021-03-25 Microcosm Technology Co., Ltd. Photosensitive polyimide resin composition and polyimide film thereof
KR102260889B1 (ko) * 2018-04-25 2021-06-04 엘티씨 주식회사 가용성 폴리이미드 수지 및 이를 포함하는 포지티브 감광성 수지 조성물
WO2022076252A1 (fr) * 2020-10-05 2022-04-14 Entegris, Inc. Composition de nettoyage de dispositifs microélectroniques
EP4105261A1 (fr) * 2021-06-14 2022-12-21 Evonik Fibres GmbH Nouvelles solutions de polyimide non toxiques

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0532953A2 (fr) * 1991-08-28 1993-03-24 Unitika Ltd. Solution de précurseur de polyimide, son procédé de préparation, masses à mouler et revêtement obtenus à partir de cette solution
WO2007047365A2 (fr) * 2005-10-13 2007-04-26 Advanced Technology Materials, Inc. Composition d'enlevement de photoresine et/ou de revetement antireflet sacrificiel, compatible avec les metaux
KR102260889B1 (ko) * 2018-04-25 2021-06-04 엘티씨 주식회사 가용성 폴리이미드 수지 및 이를 포함하는 포지티브 감광성 수지 조성물
JP2019203120A (ja) * 2018-05-16 2019-11-28 旭化成株式会社 ポリイミド前駆体樹脂組成物
US20210088903A1 (en) * 2019-01-23 2021-03-25 Microcosm Technology Co., Ltd. Photosensitive polyimide resin composition and polyimide film thereof
WO2022076252A1 (fr) * 2020-10-05 2022-04-14 Entegris, Inc. Composition de nettoyage de dispositifs microélectroniques
EP4105261A1 (fr) * 2021-06-14 2022-12-21 Evonik Fibres GmbH Nouvelles solutions de polyimide non toxiques

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