WO2023008356A1 - シンナー組成物、及び該シンナー組成物を用いた半導体デバイスの製造方法 - Google Patents

シンナー組成物、及び該シンナー組成物を用いた半導体デバイスの製造方法 Download PDF

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Publication number
WO2023008356A1
WO2023008356A1 PCT/JP2022/028578 JP2022028578W WO2023008356A1 WO 2023008356 A1 WO2023008356 A1 WO 2023008356A1 JP 2022028578 W JP2022028578 W JP 2022028578W WO 2023008356 A1 WO2023008356 A1 WO 2023008356A1
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Prior art keywords
solvent
photoresist
mass
thinner composition
methyl
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Ceased
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PCT/JP2022/028578
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English (en)
French (fr)
Japanese (ja)
Inventor
拓巳 岡田
良輔 星野
英之 佐藤
誠之 片桐
周 鈴木
雅敏 越後
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Publication date
Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc
Priority to US18/580,370 priority Critical patent/US20240361693A1/en
Priority to CN202280052673.4A priority patent/CN117716297A/zh
Priority to JP2023538508A priority patent/JPWO2023008356A1/ja
Priority to KR1020237042751A priority patent/KR20240041281A/ko
Publication of WO2023008356A1 publication Critical patent/WO2023008356A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • 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
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates
    • 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
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising layers
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • 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
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • 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
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/325—Non-aqueous compositions
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P50/00—Etching of wafers, substrates or parts of devices
    • H10P50/20—Dry etching; Plasma etching; Reactive-ion etching
    • H10P50/28—Dry etching; Plasma etching; Reactive-ion etching of insulating materials
    • H10P50/286—Dry etching; Plasma etching; Reactive-ion etching of insulating materials of organic materials
    • H10P50/287—Dry etching; Plasma etching; Reactive-ion etching of insulating materials of organic materials by chemical means
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P52/00—Grinding, lapping or polishing of wafers, substrates or parts of devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P70/00—Cleaning of wafers, substrates or parts of devices
    • H10P70/50—Cleaning of wafers, substrates or parts of devices characterised by the part to be cleaned
    • H10P70/54—Cleaning of wafer edges
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P76/00—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P76/00—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
    • H10P76/20—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials
    • H10P76/204—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials of organic photoresist masks
    • H10P76/2041—Photolithographic processes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P76/00—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
    • H10P76/20—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials
    • H10P76/204—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography of masks comprising organic materials of organic photoresist masks
    • H10P76/2041—Photolithographic processes
    • H10P76/2042—Photolithographic processes using lasers

Definitions

  • the present invention relates to a thinner composition and a method for manufacturing a semiconductor device using the thinner composition, and particularly to a thinner composition for removing a photoresist film or a photoresist underlayer film.
  • microfabrication is performed by lithography using photoresist materials.
  • lithography process a photosensitive resin composition is coated on a wafer, a designed pattern is transferred, and then a fine circuit pattern like a semiconductor integrated circuit is formed through an etching process.
  • This consists of a method of fabricating a desired fine circuit pattern through coating, exposure, development, etching and stripping steps.
  • further miniaturization of pattern dimensions is demanded in recent years as LSIs become more highly integrated and operate at higher speeds.
  • the light source for lithography used for resist pattern formation is changed from KrF excimer laser (248 nm) to ArF excimer laser (193 nm), EUV (extreme ultraviolet) light source (13 .5 nm), it is sensitive to contamination sources. Therefore, residues and contaminants of photoresist, BARC, SOC, and SOG applied to the substrate in the coating process can become a source of contamination in the exposure process, and must be removed in advance. (edge bead removing) process.
  • thinner compositions for use in various EBR processes and RRC processes have been developed, but no thinner composition has been developed that can realize them at a high level.
  • the thinner composition used in manufacturing various devices such as the EBR process and the RRC process can be sufficiently applied to the EBR process for a wide variety of photoresists and their underlying films, and the manufacturing cost is reduced. Development of a thinner composition with high RRC efficiency is required for reduction.
  • a thinner composition containing a solvent containing a compound having a specific structure is as follows.
  • R 1 is an alkyl group having 1 to 10 carbon atoms.
  • R 1 in the general formula (b-1) is a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, or t -The thinner composition according to [1] above, which is a butyl group.
  • R 1 in the general formula (b-1) is an ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, or t-butyl group
  • the thinner composition according to any one of [1] to [3] above, wherein the solvent (B) contains a solvent (B2) other than the compound (B1).
  • the solvent (B) is selected from the group consisting of methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, and methyl 3-hydroxyisobutyrate as the solvent (B2).
  • the thinner composition according to [4] above containing one or more selected.
  • a semiconductor comprising the step of coating the substrate with the thinner composition according to any one of [1] to [9] before coating the substrate with a photoresist film material or a photoresist underlayer film material. How the device is manufactured. [11] After coating a substrate with a photoresist film material or a photoresist underlayer film material, the thinner composition according to any one of the above [1] to [9] is coated on the substrate before the exposure step.
  • a method of manufacturing a semiconductor device comprising steps. [12] forming a photoresist film or a photoresist underlayer film on a substrate; and removing the photoresist film or the photoresist underlayer film using the thinner composition according to any one of [1] to [9] above.
  • R 1 is an alkyl group having 1 to 10 carbon atoms.
  • the solvent (B) is selected from the group consisting of methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, and methyl 3-hydroxyisobutyrate as the solvent (B2).
  • thinner composition of the present invention substrate processing suitable for manufacturing various devices (especially semiconductor devices) and removal of photoresist and underlying films are possible.
  • FIG. 1 is a photograph of rework performance evaluation using the thinner composition of Example A5-1a.
  • FIG. 2 is a photograph of the rework performance evaluation using the thinner composition of Comparative Example A5-1b.
  • the thinner composition of the present invention contains a solvent (B) containing a compound (B1) represented by general formula (b-1) (hereinafter also referred to as "component (B)").
  • a thinner composition of one embodiment of the present invention contains a solvent (B) containing a compound (B1) represented by the following general formula (b-1).
  • Compound (B1) may be used alone, or two or more of them may be used in combination.
  • R 1 is an alkyl group having 1 to 10 carbon atoms.
  • the said alkyl group may be a linear alkyl group, and may be a branched alkyl group.
  • the alkyl group that can be selected as R 1 includes, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, or t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group and the like.
  • R 1 in the general formula (b-1) is a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group. , s-butyl group, or t-butyl group is preferred, and ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, or t-butyl group is more preferred.
  • n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, or t-butyl group is more preferable, i-propyl group, n-butyl group, or i-butyl group is even more preferred.
  • the thinner composition of one embodiment of the present invention may contain a solvent (B2) other than the compound (B1) as the component (B).
  • the solvent (B2) include lactones such as ⁇ -butyrolactone; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl-n-pentyl ketone, methyl isopentyl ketone and 2-heptanone; ethylene glycol, diethylene glycol and propylene glycol.
  • polyhydric alcohols such as dipropylene glycol; compounds having an ester bond such as ethylene glycol monoacetate, diethylene glycol monoacetate, propylene glycol monoacetate, dipropylene glycol monoacetate; the above polyhydric alcohols or compounds having an ester bond monomethyl ether, monoethyl ether, monopropyl ether, compounds having an ether bond such as monoalkyl ether or monophenyl ether such as monobutyl ether; cyclic ethers such as dioxane, methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methyl ⁇ -methoxyisobutyrate, methyl ⁇ -methoxyisobutyrate, ethyl 2-ethoxyisobutyrate, methyl methoxypropionate, ethyl ethoxypropionate
  • the content ratio of the compound (B1) in the component (B) is adjusted to the content of the component (B ) with respect to the total amount (100% by mass), preferably 20 to 100% by mass, more preferably 30 to 100% by mass, even more preferably 50 to 100% by mass, even more preferably 60 to 100% by mass, particularly preferably is 70 to 100% by mass.
  • the component (B) used in one aspect of the present invention contains methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, and methyl 3-hydroxyisobutyrate as the solvent (B2). Containing one or more selected from the group consisting of, the solubility of the acid generator is excellent, the viewpoint of EBR performance and rework performance, and the in-plane uniformity of the coating film obtained when used as a prewetting liquid and is preferable from the viewpoint of improving the production yield of semiconductor devices.
  • methyl ⁇ -methoxyisobutyrate is preferable from the viewpoint of the solubility of the resin, that is, the removability.
  • the inclusion of methyl ⁇ -formyloxyisobutyrate and methyl ⁇ -acetyloxyisobutyrate is preferable from the viewpoint of excellent resin solubility, EBR performance and rework performance, small contact angle, and RRC performance. .
  • the inclusion of methyl 3-hydroxyisobutyrate is preferable from the viewpoint of RRC performance because the contact angle is small.
  • the method for mixing methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, or methyl 3-hydroxyisobutyrate is not particularly limited. It can be contained by either a method of adding methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate or methyl 3-hydroxyisobutyrate, or a method of mixing as a by-product or mixed in the production process of compound (B1). .
  • the content of the solvent (B2) is not limited, but is less than 112.5% by mass based on the total amount (100% by mass) of the compound (B1) from the viewpoint of improving productivity by shortening the drying time of the thinner composition. , preferably less than 100% by mass, 70% by mass or less, from the viewpoint of increasing the dissolving power of the solvent while ensuring an appropriate drying time, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20 % by mass or less, 10% by mass or less, 5% by mass or less, or 1% by mass or less is more preferable, 0.1% by mass or less is more preferable, and 0.01% by mass or less is particularly preferable.
  • the content of methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, or methyl 3-hydroxyisobutyrate is not particularly limited, but is based on the total amount (100% by mass) of the thinner composition. From the viewpoint of improving productivity by shortening the drying time of the thinner composition, it is preferably less than 100% by mass. % by mass or less, 10% by mass or less, 5% by mass or less, or 1% by mass or less is more preferable, 0.1% by mass or less is more preferable, and 0.01% by mass or less is particularly preferable.
  • the content of methyl ⁇ -methoxyisobutyrate, methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, or methyl 3-hydroxyisobutyrate is based on the total amount (100% by mass) of compound (B1) in the thinner composition.
  • Less than 112.5% by mass preferably 100% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass from the viewpoint of improving productivity by shortening the drying time of objects % or less, 20 mass % or less, 10 mass % or less, 5 mass % or less, or 1 mass % or less, more preferably 0.1 mass % or less, and particularly preferably 0.01 mass % or less. It is preferably 0.0001% by mass or more, more preferably 0.001% by mass or more, more preferably 0.01% by mass, from the viewpoint of improving the in-plane uniformity of the coating film obtained by using it as a prewetting liquid and improving the production yield of semiconductor devices. % by mass or more is more preferable. On the other hand, from the viewpoint of applicability under high-temperature conditions, it is preferable to contain more than 125% by mass based on the total amount (100% by mass) of compound (B1).
  • the solvent (B2) is one selected from the group consisting of methyl ⁇ -formyloxyisobutyrate, methyl ⁇ -acetyloxyisobutyrate, and methyl 3-hydroxyisobutyrate. Embodiments including more than one are also preferred.
  • the content of the component (B) is appropriately set according to the application, and is 50% by mass or more, 54% by mass or more, based on the total amount (100% by mass) of the thinner composition. , 58% by mass or more, 60% by mass or more, 65% by mass or more, 69% by mass or more, 74% by mass or more, 77% by mass or more, 80% by mass or more, 82% by mass or more, 84% by mass or more, 88% by mass or more , 90% by mass or more, 94% by mass or more, or 97% by mass or more.
  • the upper limit of the content of component (B) is appropriately set, but based on the total amount (100% by mass) of the thinner composition, 99% by mass or less, 98% by mass or less, 96% by mass or less, 93% by mass or less. % by mass or less, 91% by mass or less, 86% by mass or less, 81% by mass or less, 76% by mass or less, 71% by mass or less, 66% by mass or less, or 61% by mass or less.
  • the content of the component (B) can be appropriately selected from the options for the upper limit and the lower limit described above, and can be defined by any combination.
  • the thinner composition of the present invention may contain other components in addition to the above component (B) depending on the application.
  • Other components include, for example, one or more selected from surfactants and antioxidants.
  • the content of each of these other components is appropriately selected depending on the type of component, but 0.000000001 to 1 part by mass is added to 1 part by mass of component (B) contained in the thinner composition. It is preferably 0.000001 to 0.1 parts by mass, and still more preferably 0.00001 to 0.001 parts by mass.
  • ethylene glycol methyl ether ethylene glycol dimethyl ether, ethylene glycol ethyl ether, ethylene glycol methyl ethyl ether, ethylene glycol diethyl ether, diethylene glycol methyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, diethylene glycol propyl ether, diethylene glycol methyl propyl ether, diethylene glycol ethyl propyl ether, diethylene glycol dipropyl ether and the like. These can be used singly or in combination of two or more.
  • Antioxidants used in one embodiment of the present invention can be those known in the art without particular limitation, such as tocopherol-based antioxidants, phenol-based antioxidants, hindered amine-based antioxidants, and phosphorus-based antioxidants. , sulfur-based antioxidants, benzotriazole-based antioxidants, benzophenone-based antioxidants, hydroxylamine-based antioxidants, salicylate-based antioxidants, triazine-based antioxidants, and the like.
  • Tocopherol-based antioxidants are generally vitamin E, and are also naturally occurring chemical substances. Therefore, the safety is high and the environmental load is small. In addition, since it is oil-soluble and liquid at room temperature, it is also excellent in compatibility with thinner compositions and the like, and in precipitation resistance.
  • tocopherol compounds include tocopherol and its derivatives, tocotrienols and their derivatives. It is known that tocopherols and tocotrienols are classified into natural compounds (d-form), non-natural compounds (l-form), and racemic forms (dl-form) which are equivalent mixtures thereof. ing. Natural compounds (d-form) and racemic forms (dl-form) are preferred because some of them are used as food additives.
  • tocopherols include d- ⁇ -tocopherol, dl- ⁇ -tocopherol, d- ⁇ -tocopherol, dl- ⁇ -tocopherol, d- ⁇ -tocopherol, dl- ⁇ -tocopherol, dl- ⁇ -tocopherol, dl- ⁇ -tocopherol.
  • tocotrienols include d- ⁇ -tocotrienol, dl- ⁇ -tocotrienol, d- ⁇ -tocotrienol, dl- ⁇ -tocotrienol, d- ⁇ -tocotrienol, dl- ⁇ -tocotrienol, dl- ⁇ -tocotrienol, dl- ⁇ -tocotrienol.
  • tocopherol derivatives include acetates, nicotinates, linoleates, and succinates of the above tocopherols.
  • tocotrienol derivatives include acetate esters of the above tocotrienols.
  • phenol-based antioxidants include hindered phenol-based antioxidants.
  • hindered phenol antioxidants include 2,4-bis[(laurylthio)methyl]-o-cresol, 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl ), 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl), 2,4-bis-(n-octylthio)-6-(4-hydroxy-3,5 -di-t-butylanilino)-1,3,5-triazine, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,6-di-t-butyl -4-nonylphenol, 2,2'-isobutylidene-bis-(4,6-dimethyl-phenol), 4,4'-butyliden
  • oligomer type and polymer type compounds having a hindered phenol structure can also be used.
  • the phenolic antioxidants include dibutylhydroxytoluene (BHT) and hydroquinone.
  • Hindered amine antioxidants include bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis(N-methyl-2,2,6,6-tetramethyl- 4-piperidyl) sebacate, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexamethylenediamine, 2-methyl-2-(2,2,6, 6-tetramethyl-4-piperidyl)amino-N-(2,2,6,6-tetramethyl-4-piperidyl)propionamide, tetrakis(2,2,6,6-tetramethyl-4-piperidyl) ( 1,2,3,4-butanetetracarboxylate, poly[ ⁇ 6-(1,1,3,3-tetramethylbutyl)imino-1,3,5-triazine-2,4-diyl ⁇ (2 ,2,6,6-tetramethyl-4-piperidyl)imino ⁇ hexamethyl ⁇ (2,2,2,6,6-te
  • Phosphorus-based antioxidants include tris(isodecyl)phosphite, tris(tridecyl)phosphite, phenylisooctylphosphite, phenylisodecylphosphite, phenyldi(tridecyl)phosphite, and diphenylisooctyl.
  • Phosphite diphenyl isodecyl phosphite, diphenyl tridecyl phosphite, triphenyl phosphite, tris(nonylphenyl) phosphite, 4,4'-isopropylidenediphenol alkyl phosphite, trisnonylphenyl phosphite, trisdinonyl Phenylphosphite, tris(2,4-di-t-butylphenyl)phosphite, tris(biphenyl)phosphite, distearylpentaerythritol diphosphite, di(2,4-di-t-butylphenyl)pentaerythritol Diphosphite, di(nonylphenyl) pentaerythritol diphosphite, phenylbisphenol A pentaerythritol diphos
  • Sulfur-based antioxidants include 2,2-thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,4-bis[ (octylthio)methyl]-o-cresol, 2,4-bis[(laurylthio)methyl]-o-cresol, didodecyl 3,3′-thiodipropionate, dioctadecyl 3,3′-thiodipropionate, and and ditetradecyl 3,3' thiodipropionate.
  • oligomer type and polymer type compounds having a thioether structure can also be used.
  • Benzotriazole-based antioxidant As the benzotriazole-based antioxidant, an oligomer-type or polymer-type compound having a benzotriazole structure can be used.
  • Benzophenone-based antioxidants include 2-hydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, and 4-dodecyloxy-2-hydroxybenzophenone.
  • 2-hydroxy-4-octadecyloxybenzophenone 2,2'dihydroxy-4-methoxybenzophenone, 2,2'dihydroxy-4,4'-dimethoxybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone , 2-hydroxy-4-methoxy-5-sulfobenzophenone, 2-hydroxy-4-methoxy-2′-carboxybenzophenone, and 2-hydroxy-4-chlorobenzophenone.
  • oligomer type and polymer type compounds having a benzophenone structure can also be used.
  • hydroxylamine-based antioxidants examples include hydroxylamine, hydroxylamine nitrate, hydroxylamine sulfate, hydroxylamine phosphate, hydroxylamine hydrochloride, hydroxylamine citrate, and hydroxylamine oxalate. etc.
  • Salicylic acid ester antioxidants include phenyl salicylate, p-octylphenyl salicylate, and p-tertbutylphenyl salicylate.
  • oligomer type and polymer type compounds having a salicylate structure can also be used.
  • Triazine antioxidants include 2,4-bis(allyl)-6-(2-hydroxyphenyl)1,3,5-triazine and the like.
  • oligomer type and polymer type compounds having a triazine structure can also be used.
  • Such a thinner composition of the present invention can be used for various photoresist films, photoresist underlayer films (films applied to the underlayer of photoresist such as bottom antireflection plate (BARC) and spin-on carbon films) and photoresist overlayer films ( It has excellent solubility for top anti-reflective coating (TARC), and can improve EBR characteristics, rework characteristics, and coating performance of photoresist film, photoresist underlayer film, and photoresist overlayer film. Also, the RRC characteristics are excellent.
  • One embodiment of the present invention is a method of manufacturing a semiconductor device using the thinner composition of the present invention. More specifically, in one embodiment of the present invention, the thinner composition of the present invention is applied onto a substrate before the substrate is coated with a photoresist film material, a photoresist upper layer film material, or a photoresist lower layer film material.
  • a method of manufacturing a semiconductor device comprising: In another embodiment of the present invention, after coating a substrate with a photoresist film material or a photoresist underlayer film material and before the exposure step, the above-mentioned thinner composition of the present invention is applied onto the substrate.
  • a method of manufacturing a semiconductor device comprising:
  • another embodiment of the present invention comprises the steps of forming a photoresist film or a photoresist underlayer film on a substrate, and removing the photoresist film or the photoresist underlayer film using the thinner composition of the present invention.
  • a method of manufacturing a semiconductor device comprising: In this embodiment, the edge and/or back surface of the substrate on which the photoresist film or photoresist underlayer film is formed is brought into contact with the thinner composition to remove the photoresist film or photoresist underlayer film. is preferred.
  • the thinner composition is sprayed onto the edge and/or the back surface of the substrate to remove the photoresist film.
  • a mode in which the photoresist underlayer film is removed is also preferable.
  • the method further includes a step of drying the thinner composition remaining on the substrate after the step of removing the photoresist film or the photoresist underlayer film. Also, the steps of soft baking the photoresist film, partially exposing the soft baked photoresist film using a mask, and developing the exposed photoresist film with a developer to produce a An aspect further comprising a step of forming a pattern is also preferred.
  • a photoresist film or a photoresist underlayer film is formed on the edge and/or the back surface of the substrate, after forming the photoresist film or the photoresist underlayer film on the substrate, / Or an aspect further including a step of removing the photoresist film or the photoresist underlayer film on the back surface is also preferable.
  • the substrate By applying a photoresist or a photoresist underlayer film after treating the substrate with the thinner composition, the substrate can be coated with a small amount of the photoresist or the photoresist underlayer film. Cost and productivity are improved.
  • the method for manufacturing a semiconductor device of the present invention includes the step of treating the substrate with the thinner composition, then applying a photoresist or a photoresist underlayer film, and further treating the substrate with the thinner composition before the exposure step. can be provided.
  • the substrate is further treated with a thinner composition to quickly and effectively remove unnecessary photoresist and photoresist underlayer film applied to the peripheral edge portion or rear surface portion of the substrate before the exposure step. can be done.
  • Solvents used in the following examples and comparative examples are as follows.
  • iBHIB isobutyl 2-hydroxyisobutyrate, a compound in which R 1 is an i-butyl group in the general formula (b-1).
  • Acid generators used in the following examples and comparative examples are as follows.
  • Acid generator (iii): triphenylsulfonium nonafluorobutanesulfonate manufactured by Sigma-Aldrich
  • Acid generator iv): TPS-C1 (manufactured by Heraeus) ⁇ Acid generator (v): TPS-N3 (manufactured by Heraeus)
  • Resins (i) to (viii) were added to a solvent so that the resin concentration was 15 wt %, and the state after stirring at room temperature for 24 hours was visually evaluated according to the following criteria.
  • the acid generators (i) to (vii) were added to the solvent so that the concentration of the acid generator was 10 wt %, and the state after stirring at room temperature for 1 hour was visually evaluated according to the following criteria.
  • Evaluation C insoluble (visually confirm cloudy solution) The results are shown in Tables 3-6.
  • the thinner composition of the present invention When the thinner composition of the present invention is used, the solubility in resins (i) to (viii) and acid generators (i) to (vii) is excellent. It was confirmed that it was useful as a product. On the other hand, when the thinner compositions of Comparative Examples were used, some of the resins (i) to (viii) and the acid generators (i) to (vii) were found to be insoluble. It was confirmed that it was not useful as a composition.
  • HBM methyl 2-hydroxyisobutyrate (manufactured by Mitsubishi Gas Chemical Company)
  • MBM methyl ⁇ -methoxyisobutyrate (synthesized with reference to “US2014/0275016”)
  • FBM methyl ⁇ -formyloxyisobutyrate (synthesized with reference to “WO2020/004467”)
  • WO2020/004466 methyl ⁇ -acetyloxyisobutyrate (synthesized with reference to “WO2020/004466”)
  • 3HBM methyl 3-hydroxyisobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.)
  • iPHIB isopropyl 2-hydroxyisobutyrate (manufactured by Mitsubishi Gas Chemical Company, Inc.)
  • ⁇ Resin> A resin having the following composition (molecular weight) was synthesized by the above method.
  • a resin of the type shown in Table 7 was added to the thinner composition shown in Table 7 so that the resin concentration was 15 wt%, and an acid generator of the type shown in Table 7 was added so that the acid generator concentration was 1 wt%. put in.
  • the state after stirring at room temperature for 24 hours was visually evaluated according to the following criteria.
  • Evaluation S dissolution (visually confirm clear solution)
  • Evaluation A Almost dissolved (visually confirm almost clear solution)
  • Evaluation C insoluble (visually confirm cloudy solution)
  • a resin shown in Table 8 was added to the thinner composition shown in Table 8 so that the resin concentration was 40 wt %, and an acid generator of the type shown in Table 8 was added so that the acid generator concentration reached a predetermined concentration. bottom. After stirring for 1 hour at room temperature, the state was visually evaluated according to the following criteria. Evaluation S: 5 wt% dissolved (visually confirm clear solution) Evaluation A: 1 wt% dissolved (visually confirm clear solution) Evaluation C: 1 wt% insoluble (visually confirm cloudy solution) The results are shown in Tables 7 and 8.
  • the thinner compositions prepared in Examples A1-1 to A1-4 have better solubility in resins than the thinner composition of Comparative Example A1-1.
  • a thinner composition containing ⁇ FBM as the solvent (B2) in the solvent (B) exhibits high solubility in any resin and is preferably used.
  • the thinner compositions prepared in Examples A2-1a to A2-4 are superior to the thinner composition of Comparative Example A2-1 in solubility in the acid generator.
  • a thinner composition in which the solvent (B) contains ⁇ MBM, ⁇ FBM, or 3HBM as the solvent (B2) is preferably used because it exhibits high solubility in any acid generator.
  • the thinner compositions prepared in Examples A3-1a to A3-4 had a smaller contact angle than the thinner compositions in Comparative Examples A3-1a to A3-1b, and a small amount of photoresist and its underlying layer. Even a film alone can be uniformly applied to the entire surface of the substrate as a pre-wet liquid, and is suitably used in the RRC process. In other words, when the thinner composition of the present invention is used as the prewetting liquid, the contact angle becomes small when the photoresist composition or the underlayer film composition is added thereafter. As a result, a smaller amount of the photoresist composition and its underlayer film composition can be uniformly coated on the front surface of the substrate (referred to as RRC process).
  • the thinner composition containing ⁇ FBM or 3HBM as the solvent (B2) in the solvent (B) has a smaller contact angle, so that even a small amount of the photoresist or its underlying film can be uniformly applied to the entire surface of the substrate, more preferably used.
  • a thinner composition was prepared so as to have the composition shown in Table 10.
  • In-plane uniformity was evaluated. The in-plane uniformity was evaluated by measuring the thickness of the film at a total of 25 points at intervals of 3 mm apart from the center of the wafer and excluding 3 mm from the edge, and obtaining the 3 ⁇ . In-plane uniformity: Evaluation A: Less than 2.0% Evaluation B: 2.0% or more and less than 2.5% Evaluation C: 2.5% or more
  • the thinner compositions prepared in Examples A4-1a to A4-5 can form good resist films with small in-plane uniformity, and are suitably used as prewet liquids in the RRC process.
  • a thinner composition in which the solvent (B) contains ⁇ MBM, ⁇ FBM, ⁇ ABM, or 3HBM as the solvent (B2) is more preferably used because it can form a good resist film with smaller in-plane uniformity.
  • the thinner composition of the present invention has excellent rework performance. Therefore, the thinner composition of the present invention is useful as a rework liquid.
  • Example A5-1a and Comparative Example A5-1b show photographs of rework performance evaluation using the thinner compositions of Example A5-1a and Comparative Example A5-1b, respectively.
  • the thinner composition of the present invention has excellent EBR performance. Therefore, the thinner composition of the present invention is useful as an edge bead removing liquid.
  • the thinner composition of the present invention can be used for various photoresist films, photoresist underlayer films (films applied to the underlayer of photoresist such as bottom antireflective plates (BARC) and spin-on carbon films) and photoresist topcoats (top antireflection film). film (TARC)), and not only can improve EBR characteristics, rework characteristics, and coating performance of photoresist film, photoresist underlayer film and photoresist overlayer film, but also RRC Excellent properties.
  • BARC bottom antireflective plates
  • TARC top antireflection film

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WO2026009862A1 (ja) * 2024-07-05 2026-01-08 三菱瓦斯化学株式会社 除去方法、溶剤組成物、及び半導体デバイスの製造方法

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