Photoresists comprising amide component

Abstract

New photoresist compositions are provided that comprise a component that comprises an amide group and multiple hydroxyl groups. Preferred photoresists of the invention may comprise a resin with photoacid-labile groups; a photoacid generator compound; and an amide component with multiple hydroxyl groups that can function to decrease undesired photogenerated-acid diffusion out of unexposed regions of a photoresist coating layer.

Claims

1. A photoresist composition comprising: (a) a resin; (b) a photoacid generator compound; and (c) a non-polymeric amide compound that comprises i) an amide group, ii) two or more hydroxyl groups and iii) one or more cyano groups and/or one or more carboxyl group.

2. The photoresist composition of claim 1 wherein the amide compound contains a single amide moiety.

3. The photoresist composition of claim 1 wherein the amide compound corresponds to a structure of the following Formula (I): ##STR00018## wherein R1, R2 and R3 are each independently hydrogen or a non-hydrogen substituent; and R1, R2 and R3 together comprise two or more hydroxyl groups.

4. The photoresist composition of claim 3 wherein R1 is a non-hydrogen substituent and at least one of R2 and R3 are non-hydrogen substituents.

5. The photoresist composition of claim 3 wherein R1 is optionally substituted alkyl, and R2 and R3 are independently hydrogen or optionally substituted alkyl.

6. The photoresist composition of claim 3 wherein R1, R2 and R3 are each the same or different optionally substituted alkyl.

7. The photoresist of claim 3 wherein 1) R1 and R2 are taken together to provide an optionally substituted lactam group and/or 2) R2 and R3 are taken together to provide a ring structure.

8. The photoresist composition of claim 3 wherein R1 is (C.sub.1-C.sub.30)alkyl optionally substituted with a hydroxyl group, and R2 and R3 are independently hydrogen or a (C.sub.1-C.sub.30)alkyl optionally substituted with a hydroxyl group, and R1, R2 and R3 together comprise two or more hydroxyl groups.

9. The photoresist composition of claim 1 wherein the amide compound comprises three or more hydroxyl groups.

10. The photoresist composition of claim 1 wherein the amide compound comprises at least one primary hydroxyl group.

11. The photoresist composition of claim 1 wherein the amide compound comprises at least one secondary hydroxyl group.

12. The photoresist composition of claim 1 wherein the amide compound comprises one or more carboxyl groups.

13. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 2500 or less.

14. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 1500 or less.

15. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 500 or less.

16. A method for forming a photoresist relief image comprising: (a) applying a coating layer of a photoresist composition of claim 1 on a substrate; (b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

17. The method of claim 16 wherein the photoresist coating layer is immersion exposed.

18. A method for forming a photoresist relief image comprising: (a) applying on a substrate a coating layer of a photoresist composition that comprises: (i) a resin; (ii) a photoacid generator compound; and (iii) an amide compound that corresponds to a structure of the following Formula (I): ##STR00019## wherein R1 is (C.sub.1-C.sub.30)alkyl optionally substituted with a hydroxyl group, and R2 and R3 are independently hydrogen or a (C.sub.1-C.sub.30)alkyl optionally substituted with a hydroxyl group, and R1, R2 and R3 together comprise two or more hydroxyl groups, and wherein 1) R1 and R2 are taken together to provide an optionally substituted lactam group and/or 2) R2 and R3 are taken together to provide a ring structure, (b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

Description

EXAMPLES 1 AND 2 AND COMPARATIVE EXAMPLES 1 AND 2

Photoresist Preparation and Lithographic Processing

(1) Four photoresists were formulated using the components shown below in Table 1 as weight percent based on 100% solids content, with the balance of the solids being the polymer.

(2) TABLE-US-00001 TABLE 1 PGMEA HBM % Exam- (w/w of (w/w of sol- ple Polymer PAG Base SLA solvent) solvent) ids Comp. Polymer 1 PAG1 Base 1 PF656 50 50 4 Ex. 1 (100) (10%) (0.902%) (0.1%) Comp. Polymer 1 PAG1 Base 2 PF656 50 50 4 Ex. 2 (100) (10%) (1.029%) (0.1%) Ex. 1 Polymer 1 PAG1 Base 4 PF656 50 50 4 (100) (10%) (1.182%) (0.1%) Ex. 2 Polymer 1 PAG1 Base 5 PF656 50 50 4 (100) (10%) (1.049%) (0.1%) Polymer 1: IAM/ECPMA/ODOTMA/a/HAMA (20/20/30/20/10) and has Mw of 8000. PAG 1: triphenylsulfonium 1-adamantanemethoxycarbonyl-2,2-difluoromethanesulfonate Comp. Base 1: N,N-diethyl-3-oxobutanamide Comp. Base 2: N-t-butyloxycarbonyl-4-hydroxypiperidine Base 8: N-(1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl)pentanamide Base 17: 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide Surface leveling agent (SLA): fluorinated (PF 656)
Lithography Process and Results

(3) The formulated photoresists were spin coated using TEL ACT-8 (Tokyo Electron) coating track onto a 200 mm silicon wafer having as bottom antireflective coating (BARC) (AR77, Dow Electronic Materials), and soft baked at 110 C. for 60 seconds, to form a resist film of about 100 nm in thickness. The photoresist layer was exposed using an ASML/1100, 0.75 NA stepper operating at 193 nm through a photomask with PSM feature size of 90 nm 1:1 Line/Space pattern, under Annular illumination with outer/inner sigma of 0.89/0.64 with focus offset/step 0.10/0.05. The exposed wafers were post-exposed baked (PEB) at 100 C. for 60 seconds. The coated wafers were next treated with a metal ion free base developer (0.26N aqueous tetramethylammonium hydroxide solution) to develop the photoresist layer. Line Width Roughness (LWR) was determined by processing the image captured by top-down scanning electron microscopy (SEM) using a Hitachi 9380 CD-SEM, operating at an accelerating voltage of 800 volts (V), probe current of 8.0 picoamperes (pA), using 200 K magnification. LWR was measured over a 2 m line length in steps of 40 nm, and reported as the average for the measured region. Results are shown in the following Table 2.

(4) TABLE-US-00002 TABLE 2 Examples Eo LWR Comp. Ex. 1 8 13.5 Comp. Ex. 2 8.4 12.79 Ex. 1 7.6 11.3 Ex. 2 6.2 9.8

(5) In Table 2, Eo (Energy to clear is the exposure dose in mJ/cm2 of 193 wavelength radiation required to remove bulk film.

(6) In Table 2, LWR (Line width Roughness) is defined as the length width over a range of spatial frequencies. The lower the LWR value, the smoother the line.

(7) As can be seen from the above data, amide compounds with multiple hydroxyl groups of the invention provide improved lithographic performance as compared to other amide compounds that do not contain multiple hydroxyl groups.