WO2010047018A1 - Matériau de réserve et procédé de formation de motif à l'aide de celui-ci - Google Patents

Matériau de réserve et procédé de formation de motif à l'aide de celui-ci Download PDF

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Publication number
WO2010047018A1
WO2010047018A1 PCT/JP2009/003267 JP2009003267W WO2010047018A1 WO 2010047018 A1 WO2010047018 A1 WO 2010047018A1 JP 2009003267 W JP2009003267 W JP 2009003267W WO 2010047018 A1 WO2010047018 A1 WO 2010047018A1
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WO
WIPO (PCT)
Prior art keywords
poly
lactone
acid
lactoneoxystyrene
fluoroacrylate
Prior art date
Application number
PCT/JP2009/003267
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English (en)
Japanese (ja)
Inventor
遠藤政孝
笹子勝
Original Assignee
パナソニック株式会社
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Filing date
Publication date
Application filed by パナソニック株式会社 filed Critical パナソニック株式会社
Publication of WO2010047018A1 publication Critical patent/WO2010047018A1/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
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition

Definitions

  • the present invention relates to a resist material used in a semiconductor device manufacturing process or the like and a pattern forming method using the resist material.
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist film is selectively exposed through a reflective mask with exposure light composed of extreme ultraviolet rays (EUV) having a numerical aperture (NA) of 0.25 and a wavelength of 13.5 nm. 2 is irradiated to perform pattern exposure.
  • EUV extreme ultraviolet rays
  • NA numerical aperture
  • the degree of vacuum at the time of exposure is set to a high degree of vacuum of 133.3 ⁇ 10 ⁇ 6 Pa.
  • the resist film 2 subjected to pattern exposure is heated for 60 seconds at a temperature of 105 ° C. by a hot plate.
  • an object of the present invention is to obtain a fine pattern having a high development contrast in pattern formation using extreme ultraviolet rays as exposure light.
  • the component having excellent affinity with the alkaline developer is required to have a hydrophilic unit and not dissolve in the developer.
  • Examples of such components include polymers containing lactones and no acid labile groups. Lactone is known to interact with an alkaline solution, but does not affect the dissolution rate (see, for example, Non-Patent Document 1 above).
  • a polymer containing a lactone is easily dissolved in an alkaline developer under the presence of an acid labile group due to the influence of light leaking to an unexposed area. For this reason, it is calculated
  • the present invention is made on the basis of the above knowledge, and by adding a polymer having excellent affinity with an alkali developer and containing no acid labile group to a resist material used for photolithography using extreme ultraviolet light as exposure light.
  • a polymer having excellent affinity with an alkali developer and containing no acid labile group to a resist material used for photolithography using extreme ultraviolet light as exposure light.
  • it is realized by the following method.
  • the resist material according to the present invention includes a first polymer that does not contain an acid labile group and contains a lactone, a second polymer that contains an acid labile group, and a photoacid generator.
  • the first polymer containing no acid labile group and lactone contains the developer to the exposed portion in the development process after pattern exposure under high vacuum. It penetrates smoothly. For this reason, since the undeveloped residue is eliminated, a fine pattern with high development contrast can be obtained.
  • the ratio of the first polymer containing no acid labile group and containing the lactone to the second polymer containing the acid labile group may be about 5 wt% or more and 40 wt% or less.
  • a slight addition of the first polymer reduces the effect of affinity with the alkaline developer, and conversely, an excessive addition of the first polymer in the exposed area of the second polymer containing acid labile groups. This is because the original solubility may be hindered.
  • it is more preferably about 10 wt% or more and about 30 wt%.
  • ⁇ -lactone, ⁇ -lactone, ⁇ -lactone, or ⁇ -lactone can be used as the lactone in the first polymer.
  • the acid labile group in the second polymer includes t-butyl group, t-butyloxycarbonyl group, 1-ethoxyethyl group, methoxymethyl group, 2-methyladamantyl group or 2-ethyl.
  • An adamantyl group can be used.
  • the pattern forming method according to the present invention comprises a resist material comprising a first polymer that does not contain an acid labile group and contains a lactone, a second polymer that contains an acid labile group, and a photoacid generator on a substrate.
  • a step of forming a resist film comprising: a step of performing pattern exposure by selectively irradiating the resist film with exposure light comprising extreme ultraviolet rays; and developing the resist film subjected to pattern exposure. And a step of forming a resist pattern from the resist film.
  • a resist material containing a first polymer containing no acid labile group and containing a lactone, a second polymer containing an acid labile group, and a photoacid generator on a substrate In order to form the resist film, the developer is exposed to light in the development process performed after pattern exposure under high vacuum by the first polymer contained in the resist material that does not contain acid labile groups and contains lactone. It penetrates smoothly into the part. For this reason, since the undeveloped residue is eliminated, a fine pattern with high development contrast can be obtained.
  • the wavelength of extreme ultraviolet light is 13.5 nm.
  • a fine pattern with high development contrast can be obtained in pattern formation using extreme ultraviolet light as exposure light.
  • FIG. 1A to FIG. 1D are cross-sectional views showing respective steps of the pattern forming method according to the first embodiment of the present invention.
  • 2A to 2D are cross-sectional views showing respective steps of the pattern forming method according to the second embodiment of the present invention.
  • 3 (a) to 3 (d) are cross-sectional views showing respective steps of a conventional pattern forming method using extreme ultraviolet light.
  • a positive chemically amplified resist material having the following composition is prepared.
  • the resist film is selectively exposed through a reflective mask to exposure light composed of extreme ultraviolet rays (EUV) having a numerical aperture (NA) of 0.25 and a wavelength of 13.5 nm.
  • EUV extreme ultraviolet rays
  • NA numerical aperture
  • 102 is irradiated to perform pattern exposure.
  • the degree of vacuum at the time of exposure is set to a high degree of vacuum of about 133.3 ⁇ 10 ⁇ 6 Pa.
  • 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.
  • the resist film 102 is developed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, the resist film 102 is not exposed as shown in FIG. A resist pattern 102a having a good shape with a line width of 50 nm is obtained.
  • a polymer containing an acid labile group which is a base polymer of a resist material constituting the resist film 102 is added to a poly ( ⁇ -butyrolactone methacrylate which is a polymer containing no acid labile group and containing a lactone. ) Is added.
  • a poly ( ⁇ -butyrolactone methacrylate which is a polymer containing no acid labile group and containing a lactone. )
  • a positive chemically amplified resist material having the following composition is prepared.
  • the chemically amplified resist material is applied on the substrate 201. Subsequently, the applied resist material is heated with a hot plate at a temperature of 90 ° C. for 60 seconds to form a resist film 102 having a thickness of 70 nm.
  • the resist film is selectively exposed through a reflective mask with exposure light composed of extreme ultraviolet rays (EUV) having a numerical aperture (NA) of 0.25 and a wavelength of 13.5 nm.
  • EUV extreme ultraviolet rays
  • NA numerical aperture
  • the degree of vacuum at the time of exposure is set to a high degree of vacuum of about 133.3 ⁇ 10 ⁇ 6 Pa.
  • the resist film 202 that has been subjected to pattern exposure is heated by a hot plate at a temperature of 105 ° C. for 60 seconds.
  • the heated resist film 202 is developed with a tetramethylammonium hydroxide developer having a concentration of 2.38 wt%, the resist film 202 is not exposed as shown in FIG. And a resist pattern 202a having a good shape with a line width of 50 nm is obtained.
  • the polymer containing acid labile groups which is the base polymer of the resist material constituting the resist film 202
  • the poly ⁇ -pentyrolactoneoxystyrene (60 mol%)-hydroxystyrene (40 mol%)
  • the developer penetrates the exposed portion of the resist film 202 smoothly and sufficiently.
  • a fine pattern 202a having a high development contrast can be obtained.
  • poly ( ⁇ -butyrolactone methacrylate) and poly ( ⁇ -pentyrolactoneoxystyrene (60 mol%)- Hydroxystyrene (40 mol%)) was used, but instead, poly ( ⁇ -lactoneoxystyrene), poly ( ⁇ -lactoneoxystyrene-hydroxystyrene), poly ( ⁇ -lactone acrylate), poly ( ⁇ -lactone) Lactone acrylate-acrylic acid), poly ( ⁇ -lactone methacrylate), poly ( ⁇ -lactone methacrylate-methacrylic acid), poly (( ⁇ -lactone) ⁇ -fluoroacrylate), poly (( ⁇ -lactone) ⁇ -fluoroacrylate - ⁇ -fluoroacrylic acid), poly ( ⁇ -lactoneoxycarbonylmethylnorbornene), poly ( ⁇ - Lactoneoxycarbonylmethylnorbornene-hydroxycarbonylmethylnorbornene), poly ( ⁇ -lactoneoxystyrene), poly
  • the acid labile group in the base polymer is not limited to the t-butyl group and t-butyloxycarbonyl group, respectively, but includes 1-ethoxyethyl group, methoxymethyl group, 2-methyl group.
  • An adamantyl group or a 2-ethyladamantyl group can be used.
  • acrylic acid, methacrylic acid or norbornene methylhexafluoroisopropyl alcohol can be used as the repeating unit constituting the polymer, instead of hydroxystyrene, as the base polymer.
  • the photoacid generator constituting the resist material in each embodiment is not limited to triphenylsulfonium trifluoromethanesulfonic acid, but is triphenylsulfonium nonafluorobutanesulfonic acid, diphenyliodonium trifluoromethanesulfonic acid, or diphenyliodonium nonafluoro. Butanesulfonic acid can be used.
  • the quencher and the solvent of the resist material in each embodiment are only examples, and it is needless to say that resist materials having other compositions can be used as long as the resist material can form a fine pattern.
  • the resist material and the pattern forming method using the resist material according to the present invention can obtain a fine pattern having a high development contrast in pattern formation using extreme ultraviolet light as exposure light, and can be used in a semiconductor device manufacturing process and the like. This is useful for a pattern forming method using the same.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention porte sur un film de réserve (102) composé d'un matériau de réserve, qui contient un premier polymère contenant une lactone mais qui ne contient pas un groupe labile en milieu acide, un second polymère contenant un groupe labile en milieu acide, et un générateur photoacide. Ledit film de réserve est formé sur un substrat (101). Ensuite, une exposition de motif est réalisée par irradiation sélective du film de réserve (102) à l'aide d'une lumière d'exposition qui est composée d'une lumière dans l'extrême ultraviolet. Par la suite, le film de réserve à motif exposé est développé, formant, de ce fait, un motif de réserve (102a) à partir du film de réserve.
PCT/JP2009/003267 2008-10-23 2009-07-13 Matériau de réserve et procédé de formation de motif à l'aide de celui-ci WO2010047018A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008-272782 2008-10-23
JP2008272782A JP2010102061A (ja) 2008-10-23 2008-10-23 レジスト材料及びそれを用いたパターン形成方法

Publications (1)

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WO2010047018A1 true WO2010047018A1 (fr) 2010-04-29

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WO (1) WO2010047018A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102346371A (zh) * 2010-05-31 2012-02-08 罗门哈斯电子材料有限公司 光致抗蚀剂组合物以及形成光刻图案的方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6592896B2 (ja) * 2014-01-10 2019-10-23 住友化学株式会社 樹脂及びレジスト組成物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002287361A (ja) * 2001-03-28 2002-10-03 Matsushita Electric Ind Co Ltd パターン形成方法
JP2003140342A (ja) * 2001-10-31 2003-05-14 Matsushita Electric Ind Co Ltd パターン形成方法
JP2005004004A (ja) * 2003-06-12 2005-01-06 Matsushita Electric Ind Co Ltd パターン形成方法
JP2007010748A (ja) * 2005-06-28 2007-01-18 Fujifilm Holdings Corp ポジ型感光性組成物及びそれを用いたパターン形成方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002287361A (ja) * 2001-03-28 2002-10-03 Matsushita Electric Ind Co Ltd パターン形成方法
JP2003140342A (ja) * 2001-10-31 2003-05-14 Matsushita Electric Ind Co Ltd パターン形成方法
JP2005004004A (ja) * 2003-06-12 2005-01-06 Matsushita Electric Ind Co Ltd パターン形成方法
JP2007010748A (ja) * 2005-06-28 2007-01-18 Fujifilm Holdings Corp ポジ型感光性組成物及びそれを用いたパターン形成方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102346371A (zh) * 2010-05-31 2012-02-08 罗门哈斯电子材料有限公司 光致抗蚀剂组合物以及形成光刻图案的方法
CN102346371B (zh) * 2010-05-31 2013-11-20 罗门哈斯电子材料有限公司 光致抗蚀剂组合物以及形成光刻图案的方法

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