WO2009110166A1 - Matériau de résist et procédé de formation de motif l'utilisant - Google Patents

Matériau de résist et procédé de formation de motif l'utilisant Download PDF

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Publication number
WO2009110166A1
WO2009110166A1 PCT/JP2009/000141 JP2009000141W WO2009110166A1 WO 2009110166 A1 WO2009110166 A1 WO 2009110166A1 JP 2009000141 W JP2009000141 W JP 2009000141W WO 2009110166 A1 WO2009110166 A1 WO 2009110166A1
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Prior art keywords
pattern
oxide
resist
resist film
exposure
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PCT/JP2009/000141
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English (en)
Japanese (ja)
Inventor
遠藤政孝
笹子勝
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パナソニック株式会社
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Publication date
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Publication of WO2009110166A1 publication Critical patent/WO2009110166A1/fr

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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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
    • 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
    • G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing

Definitions

  • the present invention relates to a resist material used in a semiconductor device manufacturing process and the like and a pattern forming method using the resist material.
  • the region between the projection lens and the resist film on the wafer in the exposure apparatus is filled with a liquid (immersion liquid) having a refractive index of n (n> 1). Since the NA (numerical aperture) in the exposure apparatus is n ⁇ NA, the resolution of the resist film is improved.
  • Non-Patent Document 1 an acidic solution that further increases the refractive index has been proposed (see, for example, Non-Patent Document 1). This is because it is possible to design an exposure apparatus having a large NA by using a liquid having a large refractive index, and to cope with further miniaturization. However, since NA is determined by the smallest refractive index among the lens, liquid, and resist film, in order to increase NA, it is necessary to increase the refractive index of the resist film.
  • a positive resist material having the following composition is prepared. However, the resist material is in a state of being stored at room temperature for about one month after preparation.
  • the resist material is applied onto the substrate 1 to form a resist film 2 having a refractive index of 1.8 at a wavelength of 193 nm and a thickness of 0.15 ⁇ m.
  • the resist film 2 subjected to pattern exposure is heated on a hot plate at a temperature of 105 ° C. for 60 seconds, and then a tetramethyl having a concentration of 2.38 wt%.
  • a tetramethyl having a concentration of 2.38 wt% When development is performed with an aqueous ammonium hydroxide solution (alkaline developer), as shown in FIG. 7 (d), a resist pattern 2a consisting of an unexposed portion of the resist film 2 and having a line width of 0.07 ⁇ m is obtained.
  • JP-T-2006-523383 M. Switkes and M. Rothschild “Immersion lithography at 157 nm”, J. Vac. Sci. Technol., Vol. B19, p.
  • the obtained resist pattern 2a becomes a defective pattern in which defects are generated by the aggregate 6 formed by aggregation of nanoparticles in the resist material.
  • an object of the present invention is to prevent defects in a resist pattern due to a high refractive index resist material that increases the refractive index by adding nanoparticles.
  • the present inventors have added a cyclic oligomer or cyclic ether to the resist material, in addition to nanoparticles made of an inorganic oxide that increases the refractive index of the resist film. As a result, it has been found that aggregation of nanoparticles due to long-term storage after adjustment is prevented.
  • the cyclic oligomer forms a complex or a complex shape so as to surround nanoparticles made of an inorganic oxide by its cyclic structure. Thereby, it can prevent that a nanoparticle interacts and aggregates.
  • a plurality of cyclic oligomers 20 may form a complex or complex shape. Many.
  • the cyclic ether easily incorporates the metal cations 10a of the nanoparticles made of inorganic oxide into the inside due to the effect of the lone pair of oxygen atoms, and forms a complex or complex shape.
  • the nanoparticles can be prevented from interacting and aggregating.
  • the present invention it is possible to prevent resist pattern defects caused by aggregation of nanoparticles.
  • the nanoparticle which consists of inorganic oxides forms a complex or complex shape with a cyclic oligomer or cyclic ether, the characteristic does not change.
  • the present invention is made on the basis of the above knowledge, and specifically takes the following configuration.
  • the first resist material according to the present invention includes a base polymer, nanoparticles made of an inorganic oxide, and a cyclic oligomer.
  • the second resist material according to the present invention includes a base polymer, nanoparticles made of an inorganic oxide, and cyclic ether.
  • the nanoparticles include hafnium oxide (HfO 2 ), calcium oxide (CaO), magnesium oxide (MgO), zinc oxide (ZnO), and magnesium zinc oxide (Mg x Zn 1-x O, where x is 0 ⁇ x ⁇ 1), aluminum oxide (Al 2 O 3 ), silicon oxide (SiO 2 ), titanium oxide (TiO 2 ), copper oxide (Cu 2 O), zirconium oxide (Zr 2 O) 3 , ZrO 2 ) and tin oxide (SnO 2 ) can be used.
  • the diameter of the nanoparticles is preferably 1 nm or more and 100 nm or less, and more preferably 1 nm or more and 10 nm or less.
  • the cyclic oligomer includes cyclodextrin, calixarene, resorcinarene, pyrogallolarene, calixpyrrole, thiocalixarene, and thiocalixarene. At least one of homooxacalixarene can be used.
  • the cyclic ether as the cyclic ether, at least one of crown ether, cryptand, cavitand, and calceland can be used.
  • At least one of 12-crown-4, 15-crown-5 and 18-crown-6 can be used as the crown ether.
  • the particle size of the nanoparticle made of an inorganic oxide is close to 10 nm or more than 10 nm, 18-crown-6 or the like having a large size among the crown ethers is preferable because the metal cation is more easily taken into the inside. .
  • the refractive index of the resist film is improved as the amount of the inorganic oxide nanoparticles added to the resist material is increased.
  • the addition amount of the nanoparticles is desirably 20 wt% or less with respect to the polymer constituting the resist.
  • the addition amount of the cyclic oligomer to the resist material is from 1 times by weight with respect to the nanoparticles so that a complex or complex shape can be formed with the nanoparticles made of inorganic oxide. About 10 times is desirable.
  • the resist material according to the present invention is also effective for an immersion lithography method using a liquid and a normal lithography method that does not use a liquid, and a good resist pattern having no defects can be obtained.
  • a first pattern forming method includes: a step of forming a resist film on a substrate from a resist material containing a base polymer, nanoparticles made of an inorganic oxide, and a cyclic oligomer; In a state where a liquid is disposed, the method includes a step of selectively irradiating the resist film with exposure light to perform pattern exposure, and a step of developing the resist film subjected to pattern exposure to form a resist pattern. It is characterized by being.
  • a second pattern forming method includes a step of forming a resist film on a substrate from a resist material containing a base polymer, nanoparticles made of an inorganic oxide, and cyclic ether; With the liquid disposed on the resist film, the resist film is selectively irradiated with exposure light to perform pattern exposure, and the resist film subjected to pattern exposure is developed to form a resist pattern. It is characterized by having.
  • water can be used as the liquid.
  • an acidic solution can be used as the liquid.
  • a cesium sulfate aqueous solution or a phosphoric acid aqueous solution can be used as the acidic solution.
  • the immersion liquid may contain an additive such as a surfactant.
  • KrF excimer laser light, Xe 2 laser light, ArF excimer laser light, F 2 laser light, KrAr laser light, or Ar 2 laser light is used as the exposure light for immersion. be able to.
  • a third pattern forming method includes a step of forming a resist film on a substrate from a resist material containing a base polymer, nanoparticles made of an inorganic oxide, and a cyclic oligomer, and exposing light to the resist film. And a step of performing pattern exposure by selectively irradiating and a step of forming a resist pattern by developing the resist film subjected to pattern exposure.
  • a fourth pattern forming method includes a step of forming a resist film on a substrate from a resist material containing a base polymer, nanoparticles made of an inorganic oxide, and cyclic ether, and exposing light to the resist film. And a step of performing pattern exposure by selectively irradiating and a step of forming a resist pattern by developing the resist film subjected to pattern exposure.
  • the exposure light includes KrF excimer laser light, Xe 2 laser light, ArF excimer laser light, F 2 laser light, KrAr laser light, Ar 2 laser light, extreme ultraviolet (EUV)
  • EUV extreme ultraviolet
  • an electron beam (EB) can be used.
  • resist pattern defects due to a high refractive index resist material that increases the refractive index by adding nanoparticles are prevented by suppressing aggregation of nanoparticles. can do.
  • FIG. 1 is a schematic view showing a complex (complex shape) composed of a plurality of cyclic oligomers constituting the resist material according to the present invention and nanoparticles made of inorganic oxide surrounded by the plurality of cyclic oligomers. is there.
  • FIG. 2 is a schematic view showing a complex (complex shape) formed by cyclic ether constituting the resist material according to the present invention and nanoparticles made of an inorganic oxide surrounded by the cyclic ether.
  • FIG. 3A to FIG. 3D are cross-sectional views showing respective steps of the pattern forming method according to the first embodiment of the present invention.
  • FIG. 4 (a) to 4 (d) are cross-sectional views showing respective steps of the pattern forming method according to the second embodiment of the present invention.
  • FIG. 5A to FIG. 5D are cross-sectional views showing respective steps of the pattern forming method according to the third embodiment of the present invention.
  • 6 (a) to 6 (d) are cross-sectional views showing respective steps of the pattern forming method according to the fourth embodiment of the present invention.
  • 7 (a) to 7 (d) are cross-sectional views showing respective steps of a conventional pattern forming method.
  • Nanoparticle 20 which consists of inorganic oxides Cyclic oligomer 30 Cyclic ether 101 Substrate 102 Resist film 102a Resist pattern 103 Liquid 104 Exposure light 105 Projection lens 201 Substrate 202 Resist film 202a Resist pattern 203 Liquid 204 Exposure light 205 Projection lens 301 Substrate 302 resist film 302a resist pattern 303 liquid 304 exposure light 305 projection lens 401 substrate 402 resist film 402a resist pattern 403 liquid 404 exposure light 405 projection lens
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist material is prepared and stored at room temperature for about one month.
  • the resist material is applied onto the substrate 101 to form a resist film 102 having a refractive index of 1.8 at a wavelength of 193 nm and a thickness of 0.15 ⁇ m.
  • the NA is Pattern exposure is performed by irradiating the resist film 102 with exposure light 104 made of a 0.75 ArF excimer laser through a mask (not shown).
  • the resist film 102 that has been subjected to pattern exposure is heated by a hot plate at a temperature of 105 ° C. for 60 seconds. Thereafter, when development is performed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, as shown in FIG. 3D, the resist film 102 is made of an unexposed portion, and a line width of 0.07 ⁇ m is obtained. A resist pattern 102a having no aggregation of nanoparticles is obtained.
  • a cyclic oligomer that forms a complex or complex shape so as to surround a plurality of the periphery of the nanoparticles is added to the resist material. Therefore, even if the resist film 102 is formed using a resist material stored for a long time at room temperature after adjustment, the resulting resist pattern 102a has defects due to aggregation of nanoparticles. A good pattern shape that does not occur is obtained.
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist material is prepared and stored at room temperature for about one month.
  • pattern exposure is performed by irradiating the resist film 202 with exposure light 204 made of an ArF excimer laser having an NA of 0.75 and passing through a mask 203.
  • the resist film 202 subjected to the pattern exposure is heated by a hot plate at a temperature of 105 ° C. for 60 seconds. Thereafter, when development is performed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, as shown in FIG. 4D, the resist film 202 is made of an unexposed portion and has a line width of 0.07 ⁇ m. A resist pattern 202a having no aggregation of nanoparticles is obtained.
  • the second embodiment in addition to the nanoparticles made of TiO 2 that increases the refractive index, a cyclic oligomer that forms a complex or a complex shape so as to surround a plurality of the periphery of the nanoparticles. Therefore, even if the resist film 202 is formed using a resist material stored at room temperature for a long time after adjustment, the resulting resist pattern 202a has defects due to aggregation of nanoparticles. A good pattern shape that does not occur is obtained.
  • calix [4] arene is used as a cyclic oligomer that prevents aggregation of nanoparticles
  • resorcin [6] arene is used as a cyclic oligomer in the second embodiment.
  • the present invention is not limited thereto, and at least one of cyclodextrin, calixarene, resorcinarene, pyrogallol arene, calic spirol, thiocalixarene, and homooxacalixarene can be used.
  • cyclodextrin ⁇ -cyclodextrin, ⁇ -cyclodextrin, or ⁇ -cyclodextrin
  • calix [4] arene calix [6] arene or calix [8] arene can be used as the calixarene.
  • resorcinarene resorcin [4] arene
  • the present invention is not limited to these.
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist material is prepared and stored at room temperature for about one month.
  • the resist material is applied onto the substrate 301 to form a resist film 302 having a refractive index of 1.8 at a wavelength of 193 nm and a thickness of 0.15 ⁇ m.
  • the NA is Pattern exposure is performed by irradiating the resist film 302 with exposure light 304 made of a 0.75 ArF excimer laser and passing through a mask (not shown).
  • the resist film 302 subjected to pattern exposure is heated for 60 seconds at a temperature of 105 ° C. by a hot plate. Thereafter, when development is performed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, as shown in FIG. 5D, the resist film 302 is made of an unexposed portion and has a line width of 0.07 ⁇ m. A resist pattern 302a having no nanoparticles aggregation is obtained.
  • a complex or a complex shape is formed in the resist material so that cations constituting the nanoparticles are taken into the resist material. Since 18-crown-6, which is a cyclic ether, is added, even if the resist film 302 is formed using a resist material that has been stored for a long time at room temperature after the adjustment, the resulting resist pattern 302a is agglomerated nanoparticles. It becomes a good pattern shape in which no defects are caused.
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist material is prepared and stored at room temperature for about one month.
  • the resist material is applied onto the substrate 401 to form a resist film 402 having a refractive index of 1.7 at a wavelength of 193 nm and a thickness of 0.15 ⁇ m.
  • pattern exposure is performed by irradiating the resist film 402 with exposure light 404 made of an ArF excimer laser having an NA of 0.75 and passing through a mask 403.
  • the resist film 402 subjected to the pattern exposure is heated by a hot plate at a temperature of 105 ° C. for 60 seconds. Thereafter, when development is performed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, as shown in FIG. 6D, the resist film 402 is made of an unexposed portion, and a line width of 0.07 ⁇ m is obtained. A resist pattern 402a having no aggregation of nanoparticles is obtained.
  • the resist material is formed with a complex or a complex shape so that the metal cation constituting the nanoparticle is incorporated into the resist material in addition to the nanoparticle made of HfO 2 that increases the refractive index.
  • 18-crown-6 which is a cyclic ether, is added, so that even if the resist film 402 is formed using a resist material that has been stored for a long time at room temperature after the adjustment, the resulting resist pattern 402a has nanoparticle A good pattern shape in which no defects due to aggregation occur.
  • 18-crown-6 is used as the cyclic ether that prevents the aggregation of the nanoparticles, but the present invention is not limited to this, and in addition to the crown ether, cryptand, cavitand, and calceland At least one of the following can be used.
  • the crown ether at least one of 12-crown-4, 15-crown-5 and 18-crown-6 can be used.
  • the nanoparticles made of inorganic oxide include calcium oxide (CaO) in addition to hafnium oxide (HfO 2 ), titanium oxide (TiO 2 ), and silicon oxide (SiO 2 ). ), Magnesium oxide (MgO), zinc oxide (ZnO), magnesium zinc oxide (Mg x Zn 1-x O, where x is 0 ⁇ x ⁇ 1), aluminum oxide (Al 2 O 3 ), copper oxide (Cu 2 O), zirconium oxide (Zr 2 O 3 , ZrO 2 ), and tin oxide (SnO 2 ) can be used.
  • a phosphoric acid (H 3 PO 4 ) aqueous solution is used as the liquid for immersion exposure, but a cesium sulfate (Cs 2 SO 4 ) aqueous solution is used instead of the phosphoric acid aqueous solution.
  • a cesium sulfate (Cs 2 SO 4 ) aqueous solution is used instead of the phosphoric acid aqueous solution.
  • water (H 2 O) may be used.
  • ArF excimer laser light is used as exposure light. Instead, KrF excimer laser light, Xe 2 laser light, F 2 laser light, KrAr laser light, or Ar Two laser beams can be used.
  • extreme ultraviolet (EUV) or electron beam (EB) can be used for the normal exposure light according to the second or fourth embodiment, instead of the laser light.
  • EUV extreme ultraviolet
  • EB electron beam
  • the resist material according to the present invention is not limited to a positive type, and may be a negative type. Moreover, it is not restricted to a chemically amplified resist material.
  • the resist material and the pattern forming method using the same according to the present invention can prevent defects in the resist pattern due to the high refractive index resist material that increases the refractive index by adding nanoparticles, and the semiconductor device manufacturing process, etc. It is useful for a resist material used in the above and a pattern forming method using the resist material.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)

Abstract

Selon l'invention, un film de résist (102) est formé sur un substrat (101) à partir d'un matériau de résist qui contient un polymère de base, des nanoparticules composées d'un oxyde minéral et un oligomère cyclique. Ensuite, une exposition de motif est réalisée par irradiation sélective du film de résist (102) par une lumière d'exposition (104), tout en ayant un liquide (103) agencé sur le film de résist (102). Après cela, le film de résist ayant subi une exposition de motif (102) est développé, formant ainsi un motif de résist (102a).
PCT/JP2009/000141 2008-03-06 2009-01-16 Matériau de résist et procédé de formation de motif l'utilisant WO2009110166A1 (fr)

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JP2008-056567 2008-03-06
JP2008056567 2008-03-06

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014044278A (ja) * 2012-08-27 2014-03-13 Fujifilm Corp 感光性樹脂組成物、硬化膜の製造方法、硬化膜、有機ｅｌ表示装置および液晶表示装置
WO2016088655A1 (fr) * 2014-12-02 2016-06-09 Jsr株式会社 Composition de résine photosensible, procédé de fabrication de cette dernière et procédé de formation d'un motif de réserve
WO2016111300A1 (fr) * 2015-01-08 2016-07-14 Jsr株式会社 Composition sensible aux rayonnements et procédé de formation de motif
JP2016539361A (ja) * 2013-11-08 2016-12-15 東京エレクトロン株式会社 Ｅｕｖリソグラフィを加速するためのポスト処理メソッドを使用する方法
WO2017169288A1 (fr) * 2016-03-28 2017-10-05 Jsr株式会社 Composition sensible au rayonnement, et procédé de formation de motif
WO2017198418A1 (fr) * 2016-05-19 2017-11-23 Asml Netherlands B.V. Compositions de réserve
US11287740B2 (en) * 2018-06-15 2022-03-29 Taiwan Semiconductor Manufacturing Co., Ltd. Photoresist composition and method of forming photoresist pattern

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014044278A (ja) * 2012-08-27 2014-03-13 Fujifilm Corp 感光性樹脂組成物、硬化膜の製造方法、硬化膜、有機ｅｌ表示装置および液晶表示装置
JP2016539361A (ja) * 2013-11-08 2016-12-15 東京エレクトロン株式会社 Ｅｕｖリソグラフィを加速するためのポスト処理メソッドを使用する方法
KR102591306B1 (ko) * 2014-12-02 2023-10-20 제이에스알 가부시끼가이샤 포토레지스트 조성물 및 그의 제조 방법, 및 레지스트 패턴 형성 방법
WO2016088655A1 (fr) * 2014-12-02 2016-06-09 Jsr株式会社 Composition de résine photosensible, procédé de fabrication de cette dernière et procédé de formation d'un motif de réserve
KR20170093811A (ko) * 2014-12-02 2017-08-16 제이에스알 가부시끼가이샤 포토레지스트 조성물 및 그의 제조 방법, 및 레지스트 패턴 형성 방법
JPWO2016088655A1 (ja) * 2014-12-02 2017-09-14 Jsr株式会社 フォトレジスト組成物及びその製造方法並びにレジストパターン形成方法
WO2016111300A1 (fr) * 2015-01-08 2016-07-14 Jsr株式会社 Composition sensible aux rayonnements et procédé de formation de motif
JPWO2016111300A1 (ja) * 2015-01-08 2017-10-19 Jsr株式会社 感放射線性組成物及びパターン形成方法
WO2017169288A1 (fr) * 2016-03-28 2017-10-05 Jsr株式会社 Composition sensible au rayonnement, et procédé de formation de motif
JPWO2017169288A1 (ja) * 2016-03-28 2019-02-14 Jsr株式会社 感放射線性組成物及びパターン形成方法
CN109154772A (zh) * 2016-05-19 2019-01-04 Asml荷兰有限公司 抗蚀剂组合物
JP2019517025A (ja) * 2016-05-19 2019-06-20 エーエスエムエル ネザーランズ ビー．ブイ． レジスト組成物
WO2017198418A1 (fr) * 2016-05-19 2017-11-23 Asml Netherlands B.V. Compositions de réserve
CN109154772B (zh) * 2016-05-19 2023-11-07 Asml荷兰有限公司 抗蚀剂组合物
US11287740B2 (en) * 2018-06-15 2022-03-29 Taiwan Semiconductor Manufacturing Co., Ltd. Photoresist composition and method of forming photoresist pattern

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