MLchartDataset catalogue

Patent · US10042258B2 · B2 · US

Composition for forming a resist upper-layer film and method for producing a semiconductor device using the composition

(11) Publication number
US10042258B2
(21) Application number
15/324,542
(22) Filing date
2015-07-23
(30) Priority date
2014-07-24
(43) Publication date
2018-08-07
(45) Date of grant
2018-08-07
(51) IPC
C09D 125/16; C09D 161/06; G03F 7/038; G03F 7/039; G03F 7/11; G03F 7/16; G03F 7/20; G03F 7/32; G03F 7/38; G03F 7/40; H01L 21/027; C08F 220/18; C08F 220/22; C08F 220/30; G03F 7/004; G03F 7/09; H01L 21/311
(52) CPC
  • 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: 7/11, 7/004, 7/038, 7/039, 7/091, 7/094, 7/162, 7/168, 7/20, 7/2004, 7/2037, 7/322, 7/34, 7/38, 7/40
  • C08F Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds: 220/18, 220/1807, 220/22, 220/30
  • C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 8/04
  • C09D Coating compositions, e.g. paints, varnishes or lacquers; filling pastes; chemical paint or ink removers; inks; correcting fluids; woodstains; pastes or solids for colouring or printing; use of materials therefor: 125/16, 125/18, 161/06, 161/12
  • H01L Semiconductor devices; electric solid state devices not otherwise provided for: 21/0274, 21/31111
  • H10P Generic processes or apparatus for the manufacture or treatment of devices covered by class H10: 50/283, 76/20, 76/2041
(73) Assignee
Nissan Chemical Corp
(72) Inventors
Noriaki Fujitani; Takafumi Endo; Rikimaru Sakamoto
(54) Title
Composition for forming a resist upper-layer film and method for producing a semiconductor device using the composition
(57) Abstract

This composition for forming an extreme-ultraviolet (EUV) or electron-beam upper-layer resist film including (a) a polymer (P) and (b) a solvent, the solvent containing 1 to 13 mass % of a C4-12 ketone compound with respect to the entire solvent, is used in the lithography process of a procedure for manufacturing a semiconductor device. Without needing to be intermixed with a resist, and particularly on the occasion of EUV exposure, the composition for forming an EUV or electron-beam upper-layer resist film blocks undesirable exposure light, e.g., ultraviolet (UV) or deep ultraviolet (DUV) rays, and selectively transmits only the EUV rays, and can be developed using a developing solution after exposure.

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Claims (13)

  1. A composition for forming an EUV or electron beam resist upper-layer film, the composition comprising: (a) a polymer (P), and (b) a solvent, wherein the solvent contains a ketone compound having 4 to 12 carbon atoms in an amount of 1 to 13% by mass, based on a total mass of the solvent, and wherein the composition further comprises an ether compound having 8 to 16 carbon atoms as a solvent.
  2. The composition according to claim 1, wherein (a) polymer (P) comprises two or more types of repeating units and comprises all of the groups selected from the following (a1) to (a3): (a1) an alkyl group having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, (a2) a hydroxyl group and/or a carboxyl group, and (a3) an organic group having an aromatic ring.
  3. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (1-1) to (1-4): wherein, in formulae (1-1) to (1-4), Ar 1 is an organic group having an aromatic ring of 6 to 18 carbon atoms, and Ar 2 represents an organic group having an aromatic ring of 6 to 18 carbon atoms and being linked with Ar 1 through a methylene group or a tertiary carbon atom; wherein the organic group containing an aromatic ring in Ar 1 or Ar 2 comprises an alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, and a number of substitution is an integer of 1 to 10; wherein at least one of hydrogen atoms of the aromatic ring in Ar 1 or Ar 2 is substituted by a hydroxyl group and/or a carboxyl group, and is optionally substituted by a halogen atom, a nitro group, a cyano group, a methylenedioxy group, an acetoxy group, a methylthio group, an alkoxy group having 1 to 9 carbon atoms, an amino group having hydrogen atoms that may be substituted by an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms and hydrogen atoms that may be substituted by a hydroxyl group, a halogenated alkyl group having 1 to 6 carbon atoms, or a combination thereof, and a number of substitution is an integer of 1 to 10.
  4. The composition according to claim 3, wherein Ar 1 represents an organic group represented by any of the following formulae (2-1) to (2-5) or a combination thereof, and the aromatic ring in Ar 1 is appropriately linked with Ar 2, and Ar 2 represents an organic group represented by the following formula (3-1) or formula (3-2): wherein, in formulae (2-1) to (2-5) and formula (3-1) or formula (3-2), each of R 3 to R 14, R 16, and R 17 independently represents the alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom; each of T 3 to T 17 independently comprises a hydroxyl group and/or a carboxyl group and represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a methylenedioxy group, an acetoxy group, a methylthio group, an alkoxy group having 1 to 9 carbon atoms, an amino group having hydrogen atoms that may be substituted by an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms and having hydrogen atoms that may be substituted by a hydroxyl group, a halogenated alkyl group having 1 to 6 carbon atoms, or a combination thereof; each of Q 1 and Q 2 represents a single bond, an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an imino group, an arylene group having 6 to 40 carbon atoms, an alkylene group having 1 to 10 carbon atoms and having hydrogen atoms that may be substituted by a halogen atom, or a combination thereof, wherein the alkylene group optionally forms a ring; each of m1 to m4, r4, r5, r8 to r14, t4, t5, and t8 to t14 independently represents an integer of 0 to 2; each of r3, r6, r7, r17, t3, t6, t7, and t17 independently represents an integer of 0 to 8; and each of r16 and t16 independently represents an integer of 0 to 9, wherein each of the total of r3 to r14, r16, and r17 and the total of t3 to t14, t16, and t17 is independently an integer of 1 to 10.
  5. The composition according to claim 1, wherein (A) polymer (P) comprises repeating units represented by the following formulae (4-1) and (4-2): wherein, in formulae (4-1) and (4-2), R 1 and R 2 are the same or different and represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, Q 1 and Q 2 are the same or different and represent a single bond, an ester linkage (- C(═O) - O - or - O - C(═O) -), or an amide linkage (- NH - CO - or - CO - NH -), X 2 represents a single bond, an alkylene group having 1 to 10 carbon atoms, or an arylene group having 6 to 14 carbon atoms, R 1a represents an alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, n1 represents an integer of 1 to 3, and m11 represents an integer of 0 to 2.
  6. The composition according to claim 2, wherein the alkyl group (a1) is the following formula (5): wherein, in formula (5), each of W 1 and W 2 independently represents a hydrogen atom, a fluorine atom, a trifluoromethyl group, a difluoromethyl group, or a monofluoromethyl group, w 3 represents a hydrogen atom, a fluorine atom, or a combination thereof, wherein at least one of W 1, W 2, and w 3 is a fluorine atom or the fluorine-containing organic group as defined above, and m10 represents an integer of 0 to 9, wherein a number of the carbon atoms contained in formula (5) is at most 10.
  7. The composition according to claim 2, wherein the alkyl group (a1) is unsubstituted by fluorine atom.
  8. The composition according to claim 1, further comprising an acid compound and/or a basic compound.
  9. A method for producing a semiconductor device, the method comprising the steps of: forming a resist film on a substrate; applying the composition according to claim 1 to the resist film and calcining the applied composition to form a resist upper-layer film; subjecting the semiconductor substrate covered with the resist upper-layer film and the resist film to exposure with an EUV light or an electron beam through a mask pattern having a pattern for a semiconductor device; subjecting the substrate obtained after the exposure to development to remove the resist upper-layer film and the resist film to form a resist pattern; and subjecting the developed substrate to dry etching or wet etching using the resist pattern as a mask.
  10. A method for forming a resist pattern for use in producing a semiconductor device, which comprises the steps of: forming a resist film on a substrate; applying the composition according to claim 1 to the resist film and calcining the applied composition to form a resist upper-layer film; subjecting the semiconductor substrate covered with the resist upper-layer film and the resist film to exposure with an EUV light or an electron beam optionally through a mask pattern having a pattern for a semiconductor device; and subjecting the substrate obtained after the exposure to development to remove the resist upper-layer film and the resist film to form the resist pattern.
  11. A method for producing the composition according to claim 1, which comprises the step of mixing the polymer (P) and a ketone compound having 4 to 12 carbon atoms as a solvent.
  12. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (P-1) to (P-4) and (P-8) to (P-10):
  13. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (P-5) to (P-7): a copolymer of: a copolymer of: a copolymer of:

Description

The present invention relates to a composition for forming a resist upper-layer film for lithography, which is used in the semiconductor device production step using photolithography, and which is effective in reducing an adverse effect caused due to an exposure light to obtain an excellent resist pattern, and a method for forming a resist pattern using the composition for forming a resist upper-layer film for lithography as well as a method for producing a semiconductor device using the method for forming a resist pattern.

Conventionally, microfabrication using a photolithography technique has been carried out in the production of a semiconductor device. The microfabrication is a processing method in which a thin film of a photoresist composition is formed on a substrate to be processed, such as a silicon wafer, and irradiated with a ray of an active light, such as an ultraviolet light, through a mask pattern having a pattern for a semiconductor device, and subjected to development, and the substrate to be processed, such as a silicon wafer, is etched using the resultant photoresist pattern as a protective film (mask). In recent years, as the integration degree of the semiconductor device produced is being increased, an active light ray having a shorter wavelength is used, namely, the active light ray used for the processing has been changed from a KrF excimer laser (wavelength: 248 nm) to an ArF excimer laser (wavelength: 193 nm).

Citations (31)

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  • US20140080064A1
  • JP2015011169A
Record as JSON 
{
  "publication_number": "US10042258B2",
  "country": "US",
  "kind": "B2",
  "title": "Composition for forming a resist upper-layer film and method for producing a semiconductor device using the composition",
  "abstract": "This composition for forming an extreme-ultraviolet (EUV) or electron-beam upper-layer resist film including (a) a polymer (P) and (b) a solvent, the solvent containing 1 to 13 mass % of a C4-12 ketone compound with respect to the entire solvent, is used in the lithography process of a procedure for manufacturing a semiconductor device. Without needing to be intermixed with a resist, and particularly on the occasion of EUV exposure, the composition for forming an EUV or electron-beam upper-layer resist film blocks undesirable exposure light, e.g., ultraviolet (UV) or deep ultraviolet (DUV) rays, and selectively transmits only the EUV rays, and can be developed using a developing solution after exposure.",
  "claims": [
    "1. A composition for forming an EUV or electron beam resist upper-layer film, the composition comprising: (a) a polymer (P), and (b) a solvent, wherein the solvent contains a ketone compound having 4 to 12 carbon atoms in an amount of 1 to 13% by mass, based on a total mass of the solvent, and wherein the composition further comprises an ether compound having 8 to 16 carbon atoms as a solvent.",
    "2. The composition according to claim 1, wherein (a) polymer (P) comprises two or more types of repeating units and comprises all of the groups selected from the following (a1) to (a3): (a1) an alkyl group having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, (a2) a hydroxyl group and/or a carboxyl group, and (a3) an organic group having an aromatic ring.",
    "3. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (1-1) to (1-4): wherein, in formulae (1-1) to (1-4), Ar 1 is an organic group having an aromatic ring of 6 to 18 carbon atoms, and Ar 2 represents an organic group having an aromatic ring of 6 to 18 carbon atoms and being linked with Ar 1 through a methylene group or a tertiary carbon atom; wherein the organic group containing an aromatic ring in Ar 1 or Ar 2 comprises an alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, and a number of substitution is an integer of 1 to 10; wherein at least one of hydrogen atoms of the aromatic ring in Ar 1 or Ar 2 is substituted by a hydroxyl group and/or a carboxyl group, and is optionally substituted by a halogen atom, a nitro group, a cyano group, a methylenedioxy group, an acetoxy group, a methylthio group, an alkoxy group having 1 to 9 carbon atoms, an amino group having hydrogen atoms that may be substituted by an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms and hydrogen atoms that may be substituted by a hydroxyl group, a halogenated alkyl group having 1 to 6 carbon atoms, or a combination thereof, and a number of substitution is an integer of 1 to 10.",
    "4. The composition according to claim 3, wherein Ar 1 represents an organic group represented by any of the following formulae (2-1) to (2-5) or a combination thereof, and the aromatic ring in Ar 1 is appropriately linked with Ar 2, and Ar 2 represents an organic group represented by the following formula (3-1) or formula (3-2): wherein, in formulae (2-1) to (2-5) and formula (3-1) or formula (3-2), each of R 3 to R 14, R 16, and R 17 independently represents the alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom; each of T 3 to T 17 independently comprises a hydroxyl group and/or a carboxyl group and represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a methylenedioxy group, an acetoxy group, a methylthio group, an alkoxy group having 1 to 9 carbon atoms, an amino group having hydrogen atoms that may be substituted by an alkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms and having hydrogen atoms that may be substituted by a hydroxyl group, a halogenated alkyl group having 1 to 6 carbon atoms, or a combination thereof; each of Q 1 and Q 2 represents a single bond, an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an imino group, an arylene group having 6 to 40 carbon atoms, an alkylene group having 1 to 10 carbon atoms and having hydrogen atoms that may be substituted by a halogen atom, or a combination thereof, wherein the alkylene group optionally forms a ring; each of m1 to m4, r4, r5, r8 to r14, t4, t5, and t8 to t14 independently represents an integer of 0 to 2; each of r3, r6, r7, r17, t3, t6, t7, and t17 independently represents an integer of 0 to 8; and each of r16 and t16 independently represents an integer of 0 to 9, wherein each of the total of r3 to r14, r16, and r17 and the total of t3 to t14, t16, and t17 is independently an integer of 1 to 10.",
    "5. The composition according to claim 1, wherein (A) polymer (P) comprises repeating units represented by the following formulae (4-1) and (4-2): wherein, in formulae (4-1) and (4-2), R 1 and R 2 are the same or different and represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, Q 1 and Q 2 are the same or different and represent a single bond, an ester linkage (- C(═O) - O - or - O - C(═O) -), or an amide linkage (- NH - CO - or - CO - NH -), X 2 represents a single bond, an alkylene group having 1 to 10 carbon atoms, or an arylene group having 6 to 14 carbon atoms, R 1a represents an alkyl group (a1) having 1 to 10 carbon atoms and hydrogen atoms, wherein part or all of the hydrogen atoms may be substituted by a fluorine atom, n1 represents an integer of 1 to 3, and m11 represents an integer of 0 to 2.",
    "6. The composition according to claim 2, wherein the alkyl group (a1) is the following formula (5): wherein, in formula (5), each of W 1 and W 2 independently represents a hydrogen atom, a fluorine atom, a trifluoromethyl group, a difluoromethyl group, or a monofluoromethyl group, w 3 represents a hydrogen atom, a fluorine atom, or a combination thereof, wherein at least one of W 1, W 2, and w 3 is a fluorine atom or the fluorine-containing organic group as defined above, and m10 represents an integer of 0 to 9, wherein a number of the carbon atoms contained in formula (5) is at most 10.",
    "7. The composition according to claim 2, wherein the alkyl group (a1) is unsubstituted by fluorine atom.",
    "8. The composition according to claim 1, further comprising an acid compound and/or a basic compound.",
    "9. A method for producing a semiconductor device, the method comprising the steps of: forming a resist film on a substrate; applying the composition according to claim 1 to the resist film and calcining the applied composition to form a resist upper-layer film; subjecting the semiconductor substrate covered with the resist upper-layer film and the resist film to exposure with an EUV light or an electron beam through a mask pattern having a pattern for a semiconductor device; subjecting the substrate obtained after the exposure to development to remove the resist upper-layer film and the resist film to form a resist pattern; and subjecting the developed substrate to dry etching or wet etching using the resist pattern as a mask.",
    "10. A method for forming a resist pattern for use in producing a semiconductor device, which comprises the steps of: forming a resist film on a substrate; applying the composition according to claim 1 to the resist film and calcining the applied composition to form a resist upper-layer film; subjecting the semiconductor substrate covered with the resist upper-layer film and the resist film to exposure with an EUV light or an electron beam optionally through a mask pattern having a pattern for a semiconductor device; and subjecting the substrate obtained after the exposure to development to remove the resist upper-layer film and the resist film to form the resist pattern.",
    "11. A method for producing the composition according to claim 1, which comprises the step of mixing the polymer (P) and a ketone compound having 4 to 12 carbon atoms as a solvent.",
    "12. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (P-1) to (P-4) and (P-8) to (P-10):",
    "13. The composition according to claim 1, wherein (a) polymer (P) comprises repeating units represented by any of the following formulae (P-5) to (P-7): a copolymer of: a copolymer of: a copolymer of:"
  ],
  "description_excerpt": "The present invention relates to a composition for forming a resist upper-layer film for lithography, which is used in the semiconductor device production step using photolithography, and which is effective in reducing an adverse effect caused due to an exposure light to obtain an excellent resist pattern, and a method for forming a resist pattern using the composition for forming a resist upper-layer film for lithography as well as a method for producing a semiconductor device using the method for forming a resist pattern.\n\nConventionally, microfabrication using a photolithography technique has been carried out in the production of a semiconductor device. The microfabrication is a processing method in which a thin film of a photoresist composition is formed on a substrate to be processed, such as a silicon wafer, and irradiated with a ray of an active light, such as an ultraviolet light, through a mask pattern having a pattern for a semiconductor device, and subjected to development, and the substrate to be processed, such as a silicon wafer, is etched using the resultant photoresist pattern as a protective film (mask). In recent years, as the integration degree of the semiconductor device produced is being increased, an active light ray having a shorter wavelength is used, namely, the active light ray used for the processing has been changed from a KrF excimer laser (wavelength: 248 nm) to an ArF excimer laser (wavelength: 193 nm).",
  "cpc": [
    "G03F 7/11",
    "C08F 220/18",
    "C08F 220/1807",
    "C08F 220/22",
    "C08F 220/30",
    "C08G 8/04",
    "C09D 125/16",
    "C09D 125/18",
    "C09D 161/06",
    "C09D 161/12",
    "G03F 7/004",
    "G03F 7/038",
    "G03F 7/039",
    "G03F 7/091",
    "G03F 7/094",
    "G03F 7/162",
    "G03F 7/168",
    "G03F 7/20",
    "G03F 7/2004",
    "G03F 7/2037",
    "G03F 7/322",
    "G03F 7/34",
    "G03F 7/38",
    "G03F 7/40",
    "H01L 21/0274",
    "H01L 21/31111",
    "H10P 50/283",
    "H10P 76/20",
    "H10P 76/2041"
  ],
  "ipc": [
    "C09D 125/16",
    "C09D 161/06",
    "G03F 7/038",
    "G03F 7/039",
    "G03F 7/11",
    "G03F 7/16",
    "G03F 7/20",
    "G03F 7/32",
    "G03F 7/38",
    "G03F 7/40",
    "H01L 21/027",
    "C08F 220/18",
    "C08F 220/22",
    "C08F 220/30",
    "G03F 7/004",
    "G03F 7/09",
    "H01L 21/311"
  ],
  "assignees": [
    "Nissan Chemical Corp"
  ],
  "inventors": [
    "Noriaki Fujitani",
    "Takafumi Endo",
    "Rikimaru Sakamoto"
  ],
  "filing_date": "2015-07-23",
  "publication_date": "2018-08-07",
  "grant_date": "2018-08-07",
  "priority_date": "2014-07-24",
  "application_number": "US-201515324542-A",
  "family_id": "55163122",
  "cited_by_count": 1,
  "citations": [
    "JP2006113171A",
    "US8076053B2",
    "WO2007049637A1",
    "JP2012103738A",
    "US8435718B2",
    "US20120028198A1",
    "US20100003615A1",
    "JP2007219504A",
    "US20110143281A1",
    "US20070160930A1",
    "JP2007241109A",
    "JP2008065304A",
    "US20120021355A1",
    "US20130209940A1",
    "WO2012053302A1",
    "US20140113223A1",
    "JP2013033227A",
    "US20140120730A1",
    "WO2013012068A1",
    "JP2013228663A",
    "US20130059252A1",
    "US9052600B2",
    "WO2013051442A1",
    "US20140255847A1",
    "JP2013120194A",
    "US20130143163A1",
    "US20130143162A1",
    "JP2013254109A",
    "US20150140490A1",
    "US20140080064A1",
    "JP2015011169A"
  ]
}

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