WO2012161790A1 - Composition chimique concentrée et procédé d'élimination de la résine photosensible pendant une fabrication microélectronique - Google Patents

Composition chimique concentrée et procédé d'élimination de la résine photosensible pendant une fabrication microélectronique Download PDF

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Publication number
WO2012161790A1
WO2012161790A1 PCT/US2012/026480 US2012026480W WO2012161790A1 WO 2012161790 A1 WO2012161790 A1 WO 2012161790A1 US 2012026480 W US2012026480 W US 2012026480W WO 2012161790 A1 WO2012161790 A1 WO 2012161790A1
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Prior art keywords
chemical composition
concentrated chemical
composition according
approximately
solvents
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Ceased
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PCT/US2012/026480
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English (en)
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John Moore
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    • 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
    • G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
    • 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
    • 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
    • G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides

Definitions

  • Ready-to-use chemicals cannot be changed fundamentally by one or more carrier solvents or a concentration of one or more chemical additives (concentrate chemistry). Furthermore, once the ready-to-use relatively low concentration chemical additive is expired, it is typically replaced as waste.
  • liquid concentrate when initially diluted and mixed into a carrier solvent, may be used, for example, as a photoresist stripper, and during its use, additional liquid concentrate may be added to replenish the performance of the initial mixture, resulting in an extension of the working life of the original mixture and a reduction in cost.
  • the present invention generally relates to a chemical composition and method for removing photoresist during microelectronics fabrication. More specifically, the invention is a relatively highly concentrated chemical composition and method for removing photoresist during microelectronics fabrication of microelectronics devices and components.
  • the chemical composition and method is utilized as a plurality of relatively concentrated chemicals to dissolve and remove photoresist from one or more microelectronic devices or materials.
  • the chemical composition provides flexibility to a microelectronics device or material manufacturing facility by providing one or more carrier solvents, such as a suitable organic solvent or water that adjusts or customizes the chemical composition to clean the manufactured product by mixing the chemical composition at a variety of mixing ratios with the one or more carrier solvents and providing an increased working life by replenishment of an original chemical
  • composition being previously used with the relatively higher concentrated chemical composition.
  • the concentrated mixture of chemicals is in the approximate range of 10-100 times the traditional concentration of the active species of the chemical composition to conduct one or more specific photoresist or residue cleans.
  • the active species is combined with an inhibitor, a surfactant and a carrier solvent to keep the formed chemical composition and added chemicals in a liquid form.
  • the carrier solvent is chosen based on performance and selectivity in the resist removal process.
  • the carrier solvent may contain a variety of one or more organic solvents or water.
  • This replenishment effectively maintains the concentration of the active species within the resist removing medium which increases the working life of the photoresist stripper.
  • increased flexibility is offered to a manufacturing facility with one or more choices in carrier solvents existing and one or more choices in mix ratio to adjust the mixture to the needs of the product and tool and replenishment of the chemical composition to provide an increase in the product bath life.
  • microelectronics including an ability to choose a carrier solvent by which the
  • concentrated chemical composition is to be diluted within, mixing a suitable quantity of the concentrate to blend with the carrier solvent (e.g. mixing ratio) to achieve a specific performance and/or a specific selectivity (i.e. corrosion resistance) and configuring the mixtures and carrier solvents in a specific process flow defined by the number and order of steps to achieve a relatively high level of performance and selectivity.
  • a suitable quantity of the concentrate to blend with the carrier solvent e.g. mixing ratio
  • a specific selectivity i.e. corrosion resistance
  • the chemical composition includes one or more active species which exhibit acidic or alkaline chemical properties that affects the photoresist removal performance of the photoresist, one or more inhibitor or protecting agents to an underlying substrate or one or more metal features, one or more surface active agents providing sufficient wetting of the substrate without producing a foam level which prohibits sufficient tool performance and one or more solvents selected from the from the group consisting of an alcohol, an amide, an ester, an ether, a glycol ether ester, a glycol ether, a glycol, a ketone, a lactate, a sulfoxide or water.
  • the chemicals that consist of the chemical composition are present at elevated concentrations and are in a liquid form and are considered as a liquid concentrates intended to be diluted in carrier solvents at one or more points of use.
  • the chemical composition consists of an active species that is in the range of approximately 10 to 99 wt%, an inhibitor or protecting agent in the range of approximately 0.5 to 50.0 wt%, a surface active agent in the range of approximately 0.5 to 50 wt% and a solvent in the range of approximately 0.5 to 50 wt%.
  • the chemical composition is mixed as a free-flowing liquid intended to be diluted with one or more carrier solvents for use as a photoresist stripper or remover.
  • the one or more alkali active species are selected from the group consisting of ammonium hydroxide, one or more quaternary hydroxides such as tetramethyl ammonium hydroxide (TMAH), tetraethyl ammonium hydroxide (TEAH), benzyltrimethyl ammonium hydroxide (BTMAH), one or more amines such as
  • the one or more acidic active species are selected from the group of one or more alkyl-sulfonic acids such as methanesulfonic (MSA), Toluenesulfonic (TSA), dodecylbenzene sulfonic acid (DDBSA), formic acid, one or more fatty acids, sulfuric acid, nitric acid, or phosphoric acid.
  • MSA methanesulfonic
  • TSA Toluenesulfonic
  • DBSA dodecylbenzene sulfonic acid
  • formic acid one or more fatty acids, sulfuric acid, nitric acid, or phosphoric acid.
  • the one or more inhibitor or protecting agents are selected from the group consisting of one or more chelating agents, one or more complexing agents, or reducing agents such as benzylic hydroxide, catechol, triazole, imidazole, borate, one or more phosphates, and one or more alkyl or elemental silicates,
  • ethylenediaminetetraacetic acid diethylenetnaminepentaacetic acid, nitrilotriacetic acid, 2,4-pentanedione, one or more reducing sugars, one or more hydroquinones, glyoxal, salicylaldehyde, one or more fatty acids such as citric and ascorbic acid, one or more hydroxylamines, or vanillin.
  • the one or more surface active agents are selected from the group consisting of one or more nonionic, anionic, and amphoteric acting species, fluorinated, one or more nonyl-phenols, one or more nonyl-ethoxylates with a HLB (hydrophilic/lipophilic balance) ranging from 7-15, one or more alkyl-sulfonates, one or more phosphate esters, and one or more succinates.
  • HLB hydrophilic/lipophilic balance
  • the one or more solvents are selected from the group consisting of one or more ketones such as cyclohexanone, 2-heptanone, methyl propyl ketone, and methyl amyl ketone, esters such as isopropyl acetate, ethyl acetate, butyl acetate, ethyl propionate, methyl propionate, gamma- butyrolactone (BLO), ethyl 2- hydroxypropionate (ethyl lactate (EL)), ethyl 2-hydroxy-2-methyl propionate, ethyl hydroxyacetate, ethyl 2-hydroxy-3-methyl butanoate, methyl 3-methoxypropionate, ethyl 3-methoxy propionate, ethyl 3-ethoxypropionate, methyl 3-ethoxy propionate, methyl pyruvate, and ethyl pyruvate, one or more ethers and glycol ethers such as
  • the method of using the concentrated chemical composition includes diluting the concentrated chemical composition with one or more into selected carrier solvents at the point of use. Dilution may occur within a staging area or within a manufacturing lab or other suitable location.
  • the concentrated chemical composition is mixed to a desired level with one or more selected carrier solvents and then sent to the cleaning tool.
  • the mixture may be utilized at room temperature (i.e. 20 ° C). However, it is commonly heated to a predetermined temperature to achieve suitable photoresist removal performance and selectivity. Once operation begins, performance is measured by a time period allowed to completely remove the photoresist. Rinsing is conducted with DIW, typically using immersion or one or more spray methods as typically conducted by the fabrication tool operation.
  • Options utilizing the concentrated chemical composition include a plurality of variable choices and mixture of one or more carrier solvents to be added to or mixed with one or more of the carrier solvents. Additional options include using the
  • concentrated chemical composition in different formulations, such as being diluted at approximately 10% in carrier solvent X then diluting approximately 5% in carrier solvent Y or other suitable dilution percentages. Once mixed and operated over time, replenishment with the concentrated chemical composition may be performed to increase bath life.
  • the one or more carrier solvents are selected from the group consisting of one or more esters with a structure R-CO 2 Ri , one or more glycol ether esters structures, R 2 -CO 2 C 2 H 4 OC 2 H 4 -OR3, R 4 -CO 2 C 3 H 6 OC 3 H 6 -OR5 and R 6 OCO 2 R 7 , alcohols selected from structures R 8 OH, R 9 OC 2 H 4 OC 2 H 4 OH, R 10 OC 3 H 6 OC 3 H 6 OH, RiiOC 2 H 4 OH, and R-i 2 OC 3 H 6 OH, ketones selected from structures R-I 3 COR-I 4i sulfoxides selected from structure R-I 5 SOR-I 6 , and one or more amides such as N,N-dimethyl formamide, ⁇ , ⁇ -dimethyl acetamide, N-methyl pyrolidone, wherein R, R ; R 2 , R 3 , R 4 , R 5 , R 6 ,
  • the invention also comprises a method for stripping an organic substance from an inorganic substrate by bringing the composition into direct contact with the substrate, with or without heat, and for a sufficient time to dissolve the photoresist, and remove it by rinsing with water.
  • the compositions and methods have particular applicability to semiconductor wafer fabrication, for example, in the removal of photoresist and residues from semiconductor wafers. Such organic substances are present, for example, on wafers during back-end wafer-level-packaging in a wafer bumping process.
  • the compositions and methods are particularly suitable for the removal from of dry-film photoresist identified as hard-to-remove, or that material identified as resistant to conventional cleaners.
  • the present invention is to facilitate a rapid removal of photoresist without attacking (e.g. corrosion) to an underlying substrate, one or more metals, or one or more dielectrics.
  • the substrates include silicon, silicon dioxide, gallium arsenide
  • GaAs gallium arsphide
  • glass glass, sapphire, quartz, and other suitable materials.
  • features on the substrate are typically composed of metal such as copper, aluminum, nickel, titanium, and other similar layers with one or more pads, contacts, leads, and solder alloys composed of tin, lead, silver, copper, and similar materials used for conduction.
  • Other materials include dielectrics such as nitrides of silicon, polyimide, polybenzoxazole (PBO), silicone, bis- benzocyclobutene (BCB), and one or more related non-conducting films.
  • PBO polybenzoxazole
  • BCB bis- benzocyclobutene
  • the chemical composition and method teaches the ability to remove photoresist by a variety of means while achieving the desired selectivity needed to protect a wide variety of underlying materials.
  • Example #1 Photoresist stripper and detergent concentrate
  • TTA Solid 0.15% Wintrol TF-P
  • Resinall R-830 Silicon Solid 1 .45% etching inhibitor

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne une composition chimique concentrée destinée à éliminer la résine photosensible pendant une fabrication microélectronique. Selon l'invention, la composition chimique concentrée inclut une ou plusieurs substances actives qui montrent des propriétés chimiques acides ou alcalines qui affectent la performance de l'élimination de la résine photosensible, un ou plusieurs agents inhibiteurs ou de protection pour un substrat sous-jacent ou une ou plusieurs caractéristiques métalliques pour protéger le substrat et un ou plusieurs agents tensioactifs fournissant un mouillage suffisant du substrat sans produire un niveau de mousse qui empêche une performance suffisante de l'outil. La composition chimique concentrée inclut également un ou plusieurs solvants et un ou plusieurs solvants supports pour conserver la composition chimique formée sous forme liquide.
PCT/US2012/026480 2011-02-24 2012-02-24 Composition chimique concentrée et procédé d'élimination de la résine photosensible pendant une fabrication microélectronique Ceased WO2012161790A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161446210P 2011-02-24 2011-02-24
US61/446,210 2011-02-24

Publications (1)

Publication Number Publication Date
WO2012161790A1 true WO2012161790A1 (fr) 2012-11-29

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PCT/US2012/026480 Ceased WO2012161790A1 (fr) 2011-02-24 2012-02-24 Composition chimique concentrée et procédé d'élimination de la résine photosensible pendant une fabrication microélectronique

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2667254A1 (fr) * 2012-05-24 2013-11-27 Rohm and Haas Electronic Materials LLC Procédé d'enlèvement de photoréserves négatives
CN103543620A (zh) * 2013-11-11 2014-01-29 刘国政 一种印制电路板显影膜去除液
US9562211B2 (en) 2013-12-06 2017-02-07 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US9834746B2 (en) 2013-10-21 2017-12-05 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulations for removing residues on surfaces
CN111326411A (zh) * 2018-12-17 2020-06-23 许富翔 硅鳍片结构的修整方法
US11407966B2 (en) 2018-03-28 2022-08-09 Fujifilm Electronic Materials U.S.A., Inc. Cleaning compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0647884B1 (fr) * 1993-10-07 1998-04-08 MALLINCKRODT BAKER, Inc. Solution de dépouillement contenant agent réducteur pour limiter la corrosion des métaux
US6368421B1 (en) * 1998-07-10 2002-04-09 Clariant Finance (Bvi) Limited Composition for stripping photoresist and organic materials from substrate surfaces
WO2003006597A1 (fr) * 2001-07-09 2003-01-23 Mallinckrodt Baker Inc. Compositions de nettoyage de micro-elements electroniques alcalines sans ammoniac a compatibilite avec les substrats amelioree
WO2008005354A2 (fr) * 2006-06-30 2008-01-10 Fujifilm Electronic Materials U.S.A., Inc. Formulation de nettoyage pour éliminer des résidus sur des surfaces
US20090192065A1 (en) * 2005-06-16 2009-07-30 Advanced Technology Materials, Inc. Dense fluid compositions for removal of hardened photoresist, post-etch residue and/or bottom anti-reflective coating
US20100298605A1 (en) * 2008-12-26 2010-11-25 Katsutoshi Hirose process for producing a concentrated solution for a photoresist-stripping liquid having low water content

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0647884B1 (fr) * 1993-10-07 1998-04-08 MALLINCKRODT BAKER, Inc. Solution de dépouillement contenant agent réducteur pour limiter la corrosion des métaux
US6368421B1 (en) * 1998-07-10 2002-04-09 Clariant Finance (Bvi) Limited Composition for stripping photoresist and organic materials from substrate surfaces
WO2003006597A1 (fr) * 2001-07-09 2003-01-23 Mallinckrodt Baker Inc. Compositions de nettoyage de micro-elements electroniques alcalines sans ammoniac a compatibilite avec les substrats amelioree
US20090192065A1 (en) * 2005-06-16 2009-07-30 Advanced Technology Materials, Inc. Dense fluid compositions for removal of hardened photoresist, post-etch residue and/or bottom anti-reflective coating
WO2008005354A2 (fr) * 2006-06-30 2008-01-10 Fujifilm Electronic Materials U.S.A., Inc. Formulation de nettoyage pour éliminer des résidus sur des surfaces
US20100298605A1 (en) * 2008-12-26 2010-11-25 Katsutoshi Hirose process for producing a concentrated solution for a photoresist-stripping liquid having low water content

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8975008B2 (en) 2012-05-24 2015-03-10 Rohm And Haas Electronic Materials Llc Method of removing negative acting photoresists
EP2667254A1 (fr) * 2012-05-24 2013-11-27 Rohm and Haas Electronic Materials LLC Procédé d'enlèvement de photoréserves négatives
US9834746B2 (en) 2013-10-21 2017-12-05 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulations for removing residues on surfaces
CN103543620A (zh) * 2013-11-11 2014-01-29 刘国政 一种印制电路板显影膜去除液
CN103543620B (zh) * 2013-11-11 2016-07-06 深圳市星扬化工有限公司 一种印制电路板显影膜去除液
US11401487B2 (en) 2013-12-06 2022-08-02 Fujifilm Electronics Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US10253282B2 (en) 2013-12-06 2019-04-09 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US10415005B2 (en) 2013-12-06 2019-09-17 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US10696933B2 (en) 2013-12-06 2020-06-30 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US10927329B2 (en) 2013-12-06 2021-02-23 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US11286444B2 (en) 2013-12-06 2022-03-29 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US9562211B2 (en) 2013-12-06 2017-02-07 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US11618867B2 (en) 2013-12-06 2023-04-04 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US11639487B2 (en) 2013-12-06 2023-05-02 Fujifilm Electronic Materials U.S.A., Inc. Cleaning formulation for removing residues on surfaces
US11407966B2 (en) 2018-03-28 2022-08-09 Fujifilm Electronic Materials U.S.A., Inc. Cleaning compositions
CN111326411A (zh) * 2018-12-17 2020-06-23 许富翔 硅鳍片结构的修整方法

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