WO2023097826A1 - Composition de résine photosensible à film épais de source de lumière krf, son procédé de préparation et son procédé d'utilisation - Google Patents

Composition de résine photosensible à film épais de source de lumière krf, son procédé de préparation et son procédé d'utilisation Download PDF

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Publication number
WO2023097826A1
WO2023097826A1 PCT/CN2021/141097 CN2021141097W WO2023097826A1 WO 2023097826 A1 WO2023097826 A1 WO 2023097826A1 CN 2021141097 W CN2021141097 W CN 2021141097W WO 2023097826 A1 WO2023097826 A1 WO 2023097826A1
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WIPO (PCT)
Prior art keywords
monomer
krf
thick film
photoresist composition
film photoresist
Prior art date
Application number
PCT/CN2021/141097
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English (en)
Chinese (zh)
Inventor
方书农
王溯
耿志月
Original Assignee
上海新阳半导体材料股份有限公司
上海芯刻微材料技术有限责任公司
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Priority claimed from CN202111444525.0A external-priority patent/CN116203795A/zh
Priority claimed from CN202111448787.4A external-priority patent/CN116203796A/zh
Priority claimed from CN202111444417.3A external-priority patent/CN116203794A/zh
Application filed by 上海新阳半导体材料股份有限公司, 上海芯刻微材料技术有限责任公司 filed Critical 上海新阳半导体材料股份有限公司
Priority to KR1020247018789A priority Critical patent/KR20240096731A/ko
Publication of WO2023097826A1 publication Critical patent/WO2023097826A1/fr

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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • 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
    • 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
    • G03F7/322—Aqueous alkaline 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
    • G03F7/38—Treatment before imagewise removal, e.g. prebaking

Definitions

  • the invention relates to a KrF light source thick-film photoresist composition, a preparation method and a use method thereof.
  • KrF light source thick-film photoresist is used in the chip manufacturing process of LCD (liquid crystal display) / BUMP bump / MEMS micro-electromechanical / 3D-NAND memory.
  • LCD liquid crystal display
  • BUMP bump / MEMS micro-electromechanical / 3D-NAND memory.
  • This type of photoresist is different from conventional
  • the KrF thin-layer photoresist is also different from the photoresist of the ArF light source, but has its own unique properties.
  • the invention provides a kind of KrF thick-film photoresist composition, it comprises the photoacid generator shown in formula I;
  • n 0, 1, 2 or 3;
  • R1 is -COOR 1-1 or C 1-4 alkyl;
  • R 1-1 is C 1-4 alkyl;
  • R 2 is C 1-4 alkyl.
  • n 0, 1 or 2.
  • R 1 is -COOR 1-1 , wherein R 1-1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl , preferably ethyl.
  • R is methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, preferably methyl.
  • R is methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, preferably methyl.
  • the photoacid generator is preferably any one of the following compounds:
  • the KrF thick film photoresist composition includes the following components: the photoacid generator, photosensitive polymer, triethanolamine and solvent.
  • the photosensitive polymer may be a polymer capable of photochemically reacting with deep ultraviolet (DUV) light.
  • the photopolymer may be a polymer that undergoes a chemical reaction when a photoacid generator (PAG) mixed with the photopolymer is exposed to light, such as deep ultraviolet light, to generate an acid, and the acid thus generated renders the polymer A chemical reaction is performed to make the polymer either hydrophilic or hydrophobic.
  • PAG photoacid generator
  • the photopolymer does not have to be directly sensitive to light (e.g., exposure of the photopolymer to light need not alter the chemical composition of the photopolymer, although the chemical composition of the photopolymer can acid produced by PAG).
  • the solubility of photopolymers in bases can be increased due to photochemical reactions.
  • the photopolymer may have a structure in which a protecting group is bonded to a repeating unit, and the protecting group may be deprotected during exposure, so that the photopolymer is well soluble in alkali.
  • the photoresist may be a positive-tone photoresist, where portions of the photoresist removed by subsequent photoresist development are exposed to light (eg, DUV light). Deprotected protecting groups can generate new acids for chemical amplification.
  • the photosensitive polymer can be phenolic resin, polyhydroxystyrene resin, acrylic resin or a combination thereof.
  • Described phenolic resin can be the resin that has the repeating unit shown in formula (IV),
  • R 5a is an acid-dissociated protecting group
  • each of R 5b and R 5c is a hydrogen atom or a C 1 -C 6 alkyl group.
  • R 5a is C 1 -C 6 linear, branched or cyclic alkyl, vinyloxyethyl, tetrahydropyranyl, tetrahydrofuryl, trialkylsilyl, iso-norbornyl, 2- Methyl-2-adamantyl, 2-ethyl-2-adamantyl, 3-tetrahydrofuranyl, 3-oxocyclohexyl, ⁇ -butyrolactone-3-yl, mevalonolactone, ⁇ -butyrolactone-2-yl, 3-methyl- ⁇ -butyrolactone-3-yl, 2-tetrahydropyranyl, 2-tetrahydrofuryl, 2,3-propylene carbonate-1-yl, 1-methoxyethyl, 1-ethoxy
  • the linear or branched alkyl group may include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl or neopentyl.
  • the cyclic alkyl group may include, for example, cyclopentyl or cyclohexyl.
  • the polyhydroxystyrene resin may be a resin having a repeating unit represented by formula (V),
  • R 7a is a hydrogen atom or a C 1-6 alkyl group
  • R 7b is an acid-dissociated protecting group.
  • the definition of the acid-dissociated protecting group is as described above.
  • the polyhydroxystyrene resin may include another polymerizable compound as a repeating unit.
  • the polymerizable compound may include, but are not limited to: monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid; methacrylic acid derivatives, such as 2-methacryloyloxyethylsuccinic acid, 2-methacryloyloxyethylmaleic acid, 2-methacryloyloxyethylphthalic acid and 2 - methacryloxyethyl hexahydrophthalic acid; alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate and butyl (meth)acrylate; ( Hydroxyalkyl meth)acrylates such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; aryl (
  • the acrylic resin may be a resin having a repeating unit shown in formula (VI);
  • R 8a is a hydrogen atom, a C 1 -C 6 linear or branched alkyl group, a fluorine atom or a C 1 -C 6 linear or branched fluorinated alkyl group
  • R 8b is an acid Dissociated protecting group.
  • the definition of the acid-dissociated protecting group is as described above.
  • the photosensitive polymer may comprise a (meth)acrylate based polymer.
  • the (meth)acrylate-based polymer may be an aliphatic (meth)acrylate-based polymer and may include, for example, polymethyl methacrylate (PMMA), poly(tert-butyl methacrylate ), poly(methacrylic acid), poly(norbornyl methacrylate), binary or terpolymer photopolymers of repeating units of the above-mentioned (meth)acrylate-based polymers, or combinations thereof.
  • the acrylic resin may include another polymerizable compound as a repeating unit.
  • the polymerizable compound may include, but are not limited to: acrylates having ether linkages, such as 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, (methyl ) Methoxytriethylene glycol acrylate, 3-methoxybutyl (meth)acrylate, ethyl carbitol (meth)acrylate, phenoxy polyethylene glycol (meth)acrylate, ( Methoxypolyethylene glycol methacrylate, methoxypolypropylene glycol (meth)acrylate and tetrahydrofurfuryl (meth)acrylate; monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; di Carboxylic acids, such as maleic acid, fumaric acid and itaconic acid; methacrylic acid derivatives with carboxyl groups and ester bonds, such as 2-methacrylo
  • the photosensitive polymer may have the following structure:
  • the photosensitive polymer can be obtained through conventional polyaddition reactions in the art.
  • the photosensitive polymer can be obtained by carrying out polyaddition reaction of monomer A, monomer B and monomer C, and the monomer A is The monomer B is The monomer C is The molar ratio of monomer A, monomer B and monomer C is 66.5:8.5:25,
  • the solvent for the polyaddition reaction is an ester solvent, preferably ethyl acetate.
  • the temperature of the polyaddition reaction is 75-80°C, preferably 78°C.
  • the time of the polyaddition reaction is 6-10 hours, preferably 8 hours.
  • the polyaddition reaction after the polyaddition reaction is completed, it can be processed through the following post-treatment steps: 1) mixing the reaction solution with an alcohol solvent to produce a precipitate, mixing the precipitate with an ester solvent, and dissolving; 2) Repeat 1) operation 3 times, then mix with alcohol solvent to obtain precipitate, then dry it.
  • the alcohol solvent is preferably methanol.
  • the ester solvent is preferably ethyl acetate.
  • the weight average molecular weight (Mw) of the photosensitive polymer may be 10,000 to 600,000; for example, 20,000 to 400,000; and for example, 22,000.
  • Mw value may be a value measured using gel permeation chromatography (GPC) by setting polystyrene as a standard.
  • the photopolymer may have a polydispersity index (PDI) of 1 to 3, for example 2.1.
  • PDI polydispersity index
  • the preparation method of the photosensitive polymer is as follows:
  • Described KrF thick-film photoresist composition is the conventional solvent of this type of reaction in this area, is preferably ester solvent, such as propylene glycol monomethyl ether acetate.
  • the photosensitive polymer has 100 parts by weight.
  • the photoacid generator has 5 parts by weight.
  • the weight part of the triethanolamine is 0.1 part.
  • the solvent has 800 parts by weight.
  • the KrF thick film photoresist composition is composed of the above-mentioned photoacid generator, the above-mentioned photosensitive polymer, the above-mentioned triethanolamine and the above-mentioned solvent.
  • the “above” in the above-mentioned photoacid generator includes types and parts by weight; the “above” in the above-mentioned photosensitive polymers includes types and parts by weight; the “above” in the above-mentioned triethanolamine includes parts by weight; “Above” includes types and parts by weight.
  • the KrF thick-film photoresist composition is dissolved to 800 wt. parts by weight of the aforementioned photoacid generator, 100 wt. Parts of propylene glycol monomethyl ether acetate are prepared; wherein, the photosensitive polymer is obtained by carrying out polyaddition reaction of the monomer A, the monomer B and the monomer C; the polyaddition reaction
  • the photosensitive polymer is obtained by carrying out polyaddition reaction of the monomer A, the monomer B and the monomer C; the polyaddition reaction
  • Mw weight average molecular weight
  • the photosensitive polymer finally prepared is was 22,000; its polydispersity index (PDI) was 2.1.
  • the present invention also provides an application of the aforementioned compound represented by formula I as a photoacid generator in KrF thick film photoresist.
  • the present invention also provides a preparation method of the above-mentioned KrF thick-film photoresist composition, which includes the following steps: uniformly mixing the above-mentioned photoacid generator, the above-mentioned photosensitive polymer, the above-mentioned triethanolamine and the above-mentioned solvent.
  • the “above” in the above-mentioned photoacid generator includes types and parts by weight; the “above” in the above-mentioned photosensitive polymers includes types and parts by weight; the “above” in the above-mentioned triethanolamine includes parts by weight; “Above” includes types and parts by weight.
  • the mixing is a conventional operation in the art. Wherein, the temperature of the mixing is room temperature.
  • the filtering method is a conventional filtering method in the field, preferably using a filter, and the filter membrane pore size of the filter is preferably 150nm-250nm, more preferably 200nm.
  • the present invention also provides a kind of using method of above-mentioned KrF thick film photoresist composition, described method comprises the steps:
  • Step 1 coating the above-mentioned KrF thick film photoresist composition on the surface of the substrate to form a photoresist layer;
  • Step 2 Pre-baking the photoresist layer
  • Step 3 Copy the pattern on the mask plate to the pre-baked photoresist layer by exposure
  • Step 4 Baking the exposed photoresist layer
  • Step 5 Apply a developer to the baked photoresist layer for development to obtain a photoresist pattern.
  • the substrate is preferably a silicon wafer
  • step 1 the coating method is preferably spin coating
  • the thickness of the composition layer is preferably 8.5-11.5 ⁇ m, more preferably 10 ⁇ m;
  • the temperature of the pre-baking is preferably 95-125°C, more preferably 110°C;
  • the wavelength of the exposure is preferably 248nm
  • the baking temperature is preferably 110-130°C, more preferably 120°C;
  • the developer is preferably an aqueous solution of tetramethylammonium hydroxide, for example, an aqueous solution of tetramethylammonium hydroxide with a mass percentage of 2.38%;
  • the developing temperature is preferably 20-25°C, more preferably 23°C;
  • step 5 the developing time is preferably 0.5-2 min, more preferably 1 min.
  • the reagents and raw materials used in the present invention are all commercially available.
  • the positive progress effect of the present invention lies in that the photoresist film obtained by the method has good rectangularity.
  • photoacid generator 5 parts by weight of photoacid generator, 100 parts by weight of photosensitive polymer, and 0.1 part by weight of triethanolamine were dissolved into 800 parts by weight of propylene glycol monomethyl ether acetate, and mixed uniformly to prepare a photoresist composition.
  • the preparation method of photosensitive polymer is as follows:
  • Monomer A Monomer B: Monomer C:
  • the photoresist composition was filtered with a 0.2 ⁇ m membrane filter to prepare a photoresist solution.
  • a photoresist solution was spin-coated on the silicon wafer to prepare a thick-film photoresist with a thickness of 10 microns.
  • image development was performed at 23 degreeC for 1 minute with the 2.38weight% tetramethylammonium hydroxide aqueous solution. Observe resin compatibility and pattern shape.
  • Example/Comparative example Types of photoacid generators Example 1 A1 Example 2 A2 Example 3 A3 Example 4 A4 Example 5 A5 Comparative example 1 C1
  • C1-C10 The structure of C1-C10 is as follows:
  • Comparative example 10 0.15 completely dissolved good Slightly enlarged shape of the head .

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)

Abstract

L'invention concerne une composition de résine photosensible à film épais de source de lumière KrF, son procédé de préparation et son procédé d'utilisation. De façon spécifique, l'invention concerne une composition de résine photosensible à film épais de KrF contenant un générateur de photoacide représenté par la formule (I), son procédé de préparation et son procédé d'utilisation. Un film de résine photosensible formé à partir de la composition de résine photosensible présente une bonne rectangularité.
PCT/CN2021/141097 2021-11-30 2021-12-24 Composition de résine photosensible à film épais de source de lumière krf, son procédé de préparation et son procédé d'utilisation WO2023097826A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020247018789A KR20240096731A (ko) 2021-11-30 2021-12-24 KrF 광원 후막 포토레지스트 조성물, 이의 제조 방법 및 이의 사용 방법

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CN202111448787.4 2021-11-30
CN202111444525.0A CN116203795A (zh) 2021-11-30 2021-11-30 磺酸亚胺类化合物作为KrF厚膜光刻胶光产酸剂的应用
CN202111448787.4A CN116203796A (zh) 2021-11-30 2021-11-30 KrF光源厚膜光刻胶组合物的使用方法
CN202111444525.0 2021-11-30
CN202111444417.3 2021-11-30
CN202111444417.3A CN116203794A (zh) 2021-11-30 2021-11-30 KrF光源厚膜光刻胶组合物及其制备方法

Publications (1)

Publication Number Publication Date
WO2023097826A1 true WO2023097826A1 (fr) 2023-06-08

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140295347A1 (en) * 2013-03-30 2014-10-02 Rohm And Haas Electronic Materials, Llc Acid generators and photoresists comprising same
CN111176073A (zh) * 2020-01-06 2020-05-19 苏州瑞红电子化学品有限公司 一种含高耐热性羧基酚醛树脂的厚膜光刻胶组合物
CN112346300A (zh) * 2020-11-27 2021-02-09 上海新阳半导体材料股份有限公司 KrF厚膜光刻胶树脂及其制备方法和应用
CN112679499A (zh) * 2020-12-23 2021-04-20 上海博栋化学科技有限公司 一种由苦参碱合成的磺酸锍盐类光产酸剂及其合成方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140295347A1 (en) * 2013-03-30 2014-10-02 Rohm And Haas Electronic Materials, Llc Acid generators and photoresists comprising same
CN111176073A (zh) * 2020-01-06 2020-05-19 苏州瑞红电子化学品有限公司 一种含高耐热性羧基酚醛树脂的厚膜光刻胶组合物
CN112346300A (zh) * 2020-11-27 2021-02-09 上海新阳半导体材料股份有限公司 KrF厚膜光刻胶树脂及其制备方法和应用
CN112679499A (zh) * 2020-12-23 2021-04-20 上海博栋化学科技有限公司 一种由苦参碱合成的磺酸锍盐类光产酸剂及其合成方法

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