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US4837124A Expired / Lapsed US ⏱️ 0.0 years remaining

High resolution photoresist of imide containing polymers

Assignee: Clariant Finance BVI Ltd
•
Filing: 1986-02-24
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Granted: 1989-06-06
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Expires: 2006-02-24
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Abstract

Abstract Photoresist compositions suitable for deep UV and excimer laser lithography are disclosed that are mixtures of a photoacid and a polymer having imide residues to which acid labile groups are attached. These compositions provide high resolution, high contrast and high sensitivity in the deep UV (wavelength of 250-300 nm), mid-UV (wavelength of 300-350 nm) or conventional (wavelength of 350-450 nm) exposure bands. The compositions are also suitable for exposure at wavelengths commonly associated with excimer laser sources (248, 308 nm) or for exposure by X-radiation. In the compositions disclosed, the imide group ##STR1## can be blocked with certain groups, X, to form compounds containing the structure ##STR2## which have solubility properties different from the unblocked imide. These groups, X, can be cleaved by acid under the proper conditions to regenerate the unblocked imide. Also, where the imide group is incorporated in a polymer, the polymer with blocked imide groups can be made to function as a resist when compounded with a substrate capable of forming an acid upon exposure to radiation. The exact nature of the imide containing polymer is not critical, providing that: (1) in the unblocked state, the polymer is completely soluble in aqueous alkali; (2) in the blocked state, it is insoluble in the same aqueous solution, while simultaneously; (3) in the blocked state, it is soluble in a solvent capable of dissolving a suitable sensitizer; and (4) it is film forming. Other secondary properties may be selected (to enhance the characteristics of the resist) by varying the structure of the imide or a comonomer.

Inventors

  • 👤 Chengjiu Wu
  • 👤 Anne M. Mooring
  • 👤 Michael J. McFarland
  • 👤 Christopher E. Osuch
  • 👤 James T. Yardley

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 17:43
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/039; G03F7/022; G03F7/023; G03F7/0233

Claims Analysis

Total Claims: 31
Claim 1
Independent Claim 72 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing succinimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 2
Dependent Claim 72 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing succinimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 3
Dependent Claim 15 words
The photoresist composition of claim 1 wherein in the imide containing polymer is poly-co(maleimide styrene).
Claim 4
Dependent Claim 15 words
The photoresist composition of claim 1 wherein the imide containing polymer is poly-co(maleimide 4-tert-butyl styrene).
Claim 5
Dependent Claim 21 words
The photoresist composition of claim 3 wherein 50 to 100% of the imide N-H groups are replaced with acid labile groups.
Claim 6
Dependent Claim 15 words
The photoresist composition of claim 3 wherein the acid labile group is an oxycarbonyl group.
Claim 7
Dependent Claim 12 words
The photoresist composition of claim 5 wherein the oxycarbonyl group is tert-butoxycarbonyl.
Claim 8
Dependent Claim 21 words
The photoresist composition of claim 1 wherein 50 to 100% of the imide N-H groups are replaced with acid labile groups.
Claim 9
Dependent Claim 15 words
The photoresist composition of claim 1 wherein the acid labile group is an oxycarbonyl group.
Claim 10
Dependent Claim 13 words
The photoresist composition of claim 8 wherein the oxycarbonyl group is tert-butoxy carbonyl.
Claim 11
Dependent Claim 13 words
The photoresist composition of claim 8 wherein the oxycarbonyl group is benzyloxy carbonyl.
Claim 12
Dependent Claim 103 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of an iodonium salt or a sulfonium salt; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing succinimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer; and (c) a sensitizer capable of transferring energy to the iodonium or sulfonium salt is incorporated in the composition as the counter ion of the onium salt.
Claim 13
Dependent Claim 103 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of an iodonium salt or a sulfonium salt; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing succinimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer; and (c) a sensitizer capable of transferring energy to the iodonium or sulfonium salt is incorporated in the composition as the counter ion of the onium salt.
Claim 14
Dependent Claim 73 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing acyclic imide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 15
Dependent Claim 73 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing acyclic imide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 16
Dependent Claim 21 words
The photoresist composition of claim 12 wherein 50 to 100% of the imide N-H groups are replaced with acid labile groups.
Claim 17
Dependent Claim 15 words
The photoresist composition of claim 12 wherein the acid labile group is an oxycarbonyl group.
Claim 18
Dependent Claim 11 words
The photoresist composition of claim 14 wherein the oxycarbonyl is tert-butoxycarbonyl.
Claim 19
Dependent Claim 12 words
The photoresist composition of claim 14 wherein the oxycarbonyl group is benxyloxycarbonyl.
Claim 20
Dependent Claim 72 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing glutarimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 21
Dependent Claim 72 words
A photoresist composition comprising a mixture of: (a) 1 to 50 weight percent of a latent photoacid; and (b) 50 to 99 weight percent of a film forming imide containing polymer containing glutarimide residues and having a sufficient number of imide N-H groups replaced by acid labile groups to render the polymer insoluble in aqueous alkali, the composition being dissolved in a solvent which dissolves both the latent photoacid and the polymer.
Claim 22
Dependent Claim 21 words
The photoresist composition of claim 17 wherein 50 to 100% of the imide N-H groups are replaced with acid labile groups.
Claim 23
Dependent Claim 15 words
The photoresist composition of claim 17 wherein the acid labile group is an oxycarbonyl group.
Claim 24
Dependent Claim 12 words
The photoresist composition of claim 19 wherein the oxycarbonyl group is tert-butoxycarbonyl.
Claim 25
Dependent Claim 12 words
The photoresist composition of claim 19 wherein the oxycarbonyl group is benzyloxycarbonyl.
Claim 26
Dependent Claim 21 words
The photoresist composition of claims 1, 12, or 17 wherein the latent photoacid is an iodonium salt or a sulfonium salt.
Claim 27
Dependent Claim 17 words
The photoresist composition of claim 22 wherein the latent photoacid is an iodonium or sulfonium triflate salt.
Claim 28
Dependent Claim 14 words
The photoresist composition of claim 23 wherein the latent photoacid is diphenyl iodonium triflate.
Claim 29
Dependent Claim 14 words
The photoresist composition of claim 23 wherein the latent photoacid is di-4-methylphenyl iodonium triflate.
Claim 30
Dependent Claim 15 words
The photoacid composition of claim 23 wherein the latent photoacid is (4-methoxyphenyl) phenyl iodonium triflate.
Claim 31
Dependent Claim 14 words
The photoresist composition of claim 22 wherein the latent photoacid is triphenyl sulfonium triflate.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-06-05 1992-12-05 1993-06-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-06-05 1996-12-05 1997-06-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-06-05 2000-12-05 2001-06-06 $7700.00 Window Closed / Lapsed

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