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EP0227487A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Positive type radiation-sensitive resin composition

Assignee: JSR Corp
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Filing: 1986-12-29
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Granted: —
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Expires: 2006-12-29
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Abstract

Abstract A positive type radiation-sensitive resin composition which comprises a l,2-quinonediazide compound and an alkali-soluble novolac resin produced by poly­condensing phenols represented by the formulas (I) and (II) in a molar ratio of (I)/(II) of l/99 to l00/0 with a carbonyl compound: wherein R¹ and R², which may be the same or different, represent hydroxyl groups, hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups, wherein R³, R⁴ and R⁵, which may be the same or different, represent hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups. The above positive type radiation-­sensitive resin composition is excellent in dry-etching resistance, resolution and heat resistance, and appropriate as a positive type resist for producing integrated circuits in which a resist pattern is formed, and also as a positive type resist for producing a mask.

Inventors

  • 👤 Yoshihiro Hosaka
  • 👤 Ikuo Nozue
  • 👤 Masashige Takatori
  • 👤 Yoshiyuki Harita
  • 👤 Kiyoshi Honda

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-11-09 04:04
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/022; G03F7/023; G03F7/0233; G03F7/0236

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 126 words
A positive type radiation-sensitive resin composition which comprises a l,2-quinonediazide compound and an alkali-soluble novolac resin produced by poly­condensing phenols represented by the formulas (I) and (II) in a molar ratio of (I)/(II) of l/99 to l00/0 with a carbonyl compound: wherein R¹ and R², which may be the same or different, represent hydroxyl groups, hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups, wherein R³, R⁴ and R⁵, which may be the same or different, represent hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups.
Claim 2
Dependent Claim 126 words
A positive type radiation-sensitive resin composition which comprises a l,2-quinonediazide compound and an alkali-soluble novolac resin produced by poly­condensing phenols represented by the formulas (I) and (II) in a molar ratio of (I)/(II) of l/99 to l00/0 with a carbonyl compound: wherein R¹ and R², which may be the same or different, represent hydroxyl groups, hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups, wherein R³, R⁴ and R⁵, which may be the same or different, represent hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups, aroxycarbonyl groups, alkanoyloxy groups, aroyloxy groups, acyl groups, cyano groups or nitro groups.
Claim 3
Dependent Claim 42 words
A positive type radiation-sensitive resin composition according to Claim l, wherein in the formula (I), R¹ and R² are selected from hydroxyl groups, hydrogen atoms, alkyl groups, aryl groups, aralkyl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxycarbonyl groups and acyl groups.
Claim 4
Dependent Claim 79 words
A positive type radiation-sensitive resin composition according to Claim 2, wherein the alkyl groups are methyl, ethyl, propyl and butyl groups; the aryl groups are phenyl, tolyl and phenylpropyl groups; the alkenyl groups are vinyl, propenyl, allyl and butenyl groups; the aralkyl groups are benzyl, phenethyl and phenyl­propyl groups; the halogen atoms are chlorine, fluorine and bromine atoms; the alkoxy groups are methoxy, ethoxy, propoxy and butoxy groups; and the acyl groups are acetyl, propionyl, butyryl and valeryl groups.
Claim 5
Dependent Claim 50 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the phenol represented by the formula (I) is at least one compound selected from the group consisting of pyrogallol, catechol, hydroquinone, phloroglucinol, resorcinol, 5-­chlororesorcinol, 5-methylresorcinol, 2-methylresorcinol, 3,5-dihydroxydiphenyl, 3,4,5-trihydroxydiphenyl, methyl gallate, ethyl gallate, n-propyl gallate, isopropyl gallate, 4-acetoxyresorcinol and 4-acetylresorcinol.
Claim 6
Dependent Claim 33 words
A positive type radiation-sensitive resin composition according to Claim l, wherein in the formula (II), R³, R⁴ and R⁵ are selected from the group consist­ing of hydrogen atoms, alkyl groups and aryl groups.
Claim 7
Dependent Claim 31 words
A positive type radiation-sensitive resin composition according to Claim 5, wherein the alkyl groups are methyl, ethyl, propyl and butyl groups; and the aryl groups are phenyl, tolyl and cumenyl groups.
Claim 8
Dependent Claim 41 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the phenol represented by the formula (II) is at least one compound selected from the group consisting of phenol, o-cresol, m-cresol, p-cresol, 2,5-xylenol, 3,5-xylenol, 2,3,5-­trimethylphenol, o-t-butylphenol, m-t-butylphenol, p-­t-butylphenol and p-hydroxydiphenyl.
Claim 9
Dependent Claim 23 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the phenol (I) to phenol (II) molar ratio is 5/95 to l00/0.
Claim 10
Dependent Claim 43 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the carbonyl compound is represented by the formula (IV): wherein R¹⁶ and R¹⁷, which may be the same or different, represent hydrogen atoms, alkyl groups, aryl groups, alkenyl groups or aralkyl groups.
Claim 11
Dependent Claim 47 words
l0. A positive type radiation-sensitive resin composition according to Claim l, wherein the carbonyl compound is at least one compound selected from the group consisting of formaldehyde, acetaldehyde, benzaldehyde, p-hydroxybenzaldehyde, acrolein, acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, methyl phenyl ketone and methyl benzyl ketone.
Claim 12
Dependent Claim 33 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the amount of the carbonyl compound used is 0.7 to 3 moles per mole, in total, of the phenols (I) and (II).
Claim 13
Dependent Claim 36 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the l,2-­quinonediazide compound is contained in an amount of 5 to l00 parts by weight per l00 parts by weight of the alkali-soluble novolac resin.
Claim 14
Dependent Claim 105 words
A positive type radiation-sensitive resin composition according to Claim l, wherein the l,2-­quinonediazide compound is at least one compound selected from the group consisting of l,2-quinonediazidesulfonic acid esters of (poly)hydroxybenzenes, l,2-quinone­diazidesulfonic acid esters of (poly)hydroxyphenyl alkyl ketones or (poly)hydroxyphenyl aryl ketones, l,2-­quinonediazidesulfonic acid esters of bis[(poly)hydroxy­phenyl]alkanes, l,2-quinonediazidesulfonic acid esters of alkyl (poly)hydroxybenzoates or aryl (poly)hydroxy­benzoates, l,2-quinonediazidesulfonic acid esters of bis[(poly)hydroxybenzoyl]alkanes or bis[(poly)hydroxy­benzoyl]benzenes, l,2-quinonediazidesulfonic acid esters of (poly)ethylene glycol-di[(poly)hydroxybenzoates], l,2-quinonediazidesulfonic acid esters of α-pyrone type natural coloring matters having hydroxyl groups, l,2-­quinonediazidesulfonic acid esters of γ-pyrone type natural coloring matters having hydroxyl groups and l,2-quinonediazidesulfonic acid esters of diazine type natural coloring matters having hydroxyl groups.
Claim 15
Dependent Claim 137 words
A positive type radiation-sensitive resin composition which comprises l00 parts by weight of an alkali-soluble resin and 5 to l00 parts by weight of a l,2-quinonediazide compound represented by the formula (III): wherein R⁶ to R¹⁵, which may be the same or different, represent hydroxyl groups, l,2-quinonediazidesulfonyl groups, hydrogen atoms, alkyl groups having l to 4 carbon atoms, alkoxy groups having l to 4 carbon atoms, halogen atoms, cyano groups, nitro groups, acyl groups having 2 to 5 carbon atoms and aralkyl groups having 7 to 9 carbon atoms, and wherein the number (n) of the hydroxyl groups in the formula (III) is 0 or an integer of l to 9, the number (m) of the l,2-quinonediazidesulfonyl groups in the formula (III) is an integer of l to l0 and 5 ≦ n + m ≦ l0.
Claim 16
Dependent Claim 137 words
A positive type radiation-sensitive resin composition which comprises l00 parts by weight of an alkali-soluble resin and 5 to l00 parts by weight of a l,2-quinonediazide compound represented by the formula (III): wherein R⁶ to R¹⁵, which may be the same or different, represent hydroxyl groups, l,2-quinonediazidesulfonyl groups, hydrogen atoms, alkyl groups having l to 4 carbon atoms, alkoxy groups having l to 4 carbon atoms, halogen atoms, cyano groups, nitro groups, acyl groups having 2 to 5 carbon atoms and aralkyl groups having 7 to 9 carbon atoms, and wherein the number (n) of the hydroxyl groups in the formula (III) is 0 or an integer of l to 9, the number (m) of the l,2-quinonediazidesulfonyl groups in the formula (III) is an integer of l to l0 and 5 ≦ n + m ≦ l0.

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