Compositions comprising sulfonamide material and processes for photolithography

Abstract

New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more materials that have sulfonamide substitution. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer during immersion lithography processing.

Claims

1. A method for processing a photoresist composition, comprising: (a) applying on a substrate a photoresist composition to form a photoresist layer, wherein the photoresist composition comprises: (i) one or more resins, (ii) a photoactive component, and (iii) one or more polymers that comprise: 1) a group of the formula RS(O).sub.2(X)NR.sub.2 where X is a 1 to 8 carbon linkage, R is a non-hydrogen substituent, and each R is independently a hydrogen or non-hydrogen substituent, and 2) one or more photoacid-labile groups wherein the iii) one or more polymers are different from the one or more resins; and (b) immersion exposing the photoresist layer to radiation activating for the photoresist composition.

2. The method of claim 1 wherein the iii) one or more polymers comprise one or more electron-withdrawing moieties.

3. The method of claim 1 wherein the iii) one or more polymers comprise one more fluorine atoms or fluorine-substituted groups.

4. A photoresist composition comprising: (i) one or more resins, (ii) a photoactive component in an amount sufficient to create a latent image in a coating layer of the photoresist composition upon exposure to activating radiation, and (iii) one or more polymers that comprise a group of the formula RS(O).sub.2(X)NR.sub.2 where X is a 1 to 8 carbon linkage, R is a non-hydrogen substituent, and each R is independently a hydrogen or non-hydrogen substituent, and the one or more polymers comprise one or more photoacid-labile groups, wherein the (iii) one or more polymers are distinct from the one or more resins.

5. The photoresist composition of claim 4 wherein the one or more polymers comprise aqueous base-solubilizing groups other than the group of formula RS(O).sub.2(X)NR.sub.2.

6. The photoresist composition of claim 4 wherein the photoresist composition comprises a tetrapolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

7. The photoresist composition of claim 4 wherein the photoresist composition comprises a pentapolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

8. The photoresist composition of claim 4 wherein the photoresist composition comprises a terpolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

9. A photoresist composition comprising: (i) one or more resins, (ii) a photoactive component in an amount sufficient to create a latent image in a coating layer of the photoresist composition upon exposure to activating radiation, and (iii) one or more tetrapolymers, pentapolymers and/or terpolymers that comprise a comprise a group of the formula RS(O).sub.2(X)NR.sub.2 where X is a 1 to 8 carbon linkage, R is a non-hydrogen substituent, and each R is independently a hydrogen or non-hydrogen substituent, wherein the (iii) one or more polymers are distinct from the one or more resins.

10. The photoresist composition of claim 9 wherein the photoresist composition comprises a tetrapolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

11. The photoresist composition of claim 9 wherein the photoresist composition comprises a pentapolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

12. The photoresist composition of claim 9 wherein the photoresist composition comprises a terpolymer that comprises a group of the formula RS(O).sub.2(X)NR.sub.2.

Description

EXAMPLE 1

Sulfonamide Resin Preparation

(1) A sulfonamide copolymer resin having the following structure was prepared as described below:

(2) ##STR00005##
A. Monomer and initiator mixture: weigh 7.00 g of CH.sub.3(CHCH)C(O)OCH(CH.sub.3)CH.sub.2C(CH.sub.3).sub.2OH (the first monomer), 2.80 g of (CH.sub.2CH)C(O)OC(CH2).sub.2NHSO.sub.2CF.sub.3 (the second monomer) 0.42 g of Trignox-23 (initiator) and 17.0 g PGMEA (solvent) into a feeding vial.
B. Reactor: 30 g of PGMEA in a reactor and maintain at 85 C.
C. Feed A into B: A is fed into B with a constant feeding rate in 120 minutes.
D. Holding temperature: after feeding A into B, the temperature of the reactor is maintained at 85 C. for additional two hrs, then allow the reactor temp to cool down naturally to room temperature.

(3) The sulfonamide resin from the reactor can be used in a photoresist composition without further purification.

EXAMPLE 2

Additional Sulfonamide Resin Preparation

(4) By procedures similar to those of Example 1, the following sulfonamide resin is prepared:

(5) ##STR00006##

EXAMPLE 3

Photoresist Preparation and Processing

(6) A photoresist composition is prepared by admixing the following materials in the specified amounts:

(7) 1. Resin component: Terpolymer of (2-methyl-2-adamantyl methacrylate/beta-hydroxy-gamma-butyrolactone methacrylate/cyano-norbornyl methacrylate in an amount of 6.79 weight % based on total weight of the photoresist composition;

(8) 2. Photoacid generator compound: T-butyl phenyl tetramethylene sulfonium perfluorobutanesulfonate in an amount of 0.284 weight % based on total weight of the photoresist composition;

(9) 3. Base additive: N-Alkyl Caprolactam in an amount of 0.017 weight % based on total weight of the photoresist composition;

(10) 4. Surfactant: R08 (fluorine-containing surfactant, available from Dainippon Ink & Chemicals, Inc.) in an amount of 0.0071 weight % based on total weight of the photoresist composition

(11) 5. Substantially non-mixable additive: Polymer of Example 1 prepared as described in Example 1 above and in an amount of 0.213 weight % based on total weight of the photoresist composition.

(12) 6. Solvent component: propylene glycol monomethyl ether acetate to provide about a 90 percent fluid composition.

(13) This photoresist composition containing is spin-coated onto silicon wafers, dried on vacuum hotplate to remove soft-plate and then exposed in an immersion lithography process with aqueous immersion fluid directly contacting the dried photoresist layers. In that immersion system, the photoresist layers is exposed to patterned 193 nm radiation at a dose of 24.1 mJ/cm.sup.2.

(14) The photoresist layers is then post-exposed baked (such as at about 120 C.) and developed with 0.26N alkaline aqueous developer solution.

(15) To evaluate leaching of resist components after the post-exposure bake and before development, the immersion fluid is evaluated for the photoacid in the resist and its photo-degradation byproducts by LC/mass spectroscopy (60 second leaching time tested).