Photoresist pattern trimming compositions and methods

Patent metadata

Field	Value
Publication number	US-9696629-B2
Application number	US-201514971087-A
Country	US
Kind code	B2
Filing date	Dec 16, 2015
Priority date	Dec 31, 2014
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

Photoresist pattern trimming compositions are provided. The compositions comprise: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group. Also provided are methods of trimming a photoresist pattern using the trimming compositions. The compositions and methods find particular applicability in the manufacture of semiconductor devices.

First claim

What is claimed is:

1. A photoresist pattern trimming composition, comprising: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group.

2. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group comprises a fluorine atom bonded to a carbon at the alpha position of the alcohol hydroxyl.

3. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group comprises a fluorinated group bonded pendant to a carbon at the alpha position of the alcohol hydroxyl.

4. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid comprises a hexafluoroalcohol group.

5. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid comprises a plurality of fluorinated alcohol groups.

6. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group is bonded to an aromatic ring of the aromatic sulfonic acid through an ester group.

7. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid is chosen from the following acids:

8. The photoresist pattern trimming composition of claim 1 , wherein the matrix polymer is a poly(meth)acrylate polymer.

9. A method of trimming a photoresist pattern, comprising:
(a) providing a semiconductor substrate;
(b) forming a photoresist pattern on the substrate, wherein the photoresist pattern is formed from a photoresist composition comprising: a matrix polymer comprising an acid labile group, a photoacid generator, and a solvent;
(c) coating a photoresist trimming composition of claim 1 on the substrate over the photoresist pattern;
(d) heating the coated substrate, thereby causing a change in polarity of the photoresist matrix polymer in a surface region of the photoresist pattern; and
(e) contacting the photoresist pattern with a rinsing agent to remove the surface region of the photoresist pattern, thereby forming a trimmed photoresist pattern.

10. The method of claim 9 , wherein the photoresist pattern is formed in an immersion lithography process.

11. The method of claim 9 , wherein the fluorinated alcohol group comprises a fluorine atom bonded to a carbon at the alpha position of the alcohol hydroxyl.

12. The method of claim 9 , wherein the fluorinated alcohol group comprises a fluorinated group bonded pendant to a carbon at the alpha position of the alcohol hydroxyl.

13. The method of claim 9 , wherein the aromatic sulfonic acid comprises a hexafluoroalcohol group.

14. The method of claim 9 , wherein the aromatic sulfonic acid comprises a plurality of fluorinated alcohol groups.

15. The method of claim 9 , wherein the fluorinated alcohol group is bonded to an aromatic ring of the aromatic sulfonic acid through an ester group.

16. The method of claim 9 , wherein the aromatic sulfonic acid is chosen from the following acids:

17. The method of claim 9 , wherein the matrix polymer is a poly(meth)acrylate polymer.

18. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid is represented by the following general formula (I):

wherein Ar 1 represents an optionally substituted aromatic group; R 1 independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; Y independently represents a linking group; Z independently represents a group chosen from fluorinated alcohols, fluorinated esters, substituted or unsubstituted alkyl, C5 or higher monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a fluorinated alcohol group; a is an integer of 0 or greater; b is an integer of 1 or greater; c is an integer of 1 or greater; and a+ b+ c is at least 2 and not greater than the total number of available aromatic carbon atoms of Ar 1.

19. The photoresist pattern trimming composition of claim 1 , wherein the aromatic acid is present in an amount of from 0.01 to 20 wt% based on total solids of the trimming composition.

20. The method of claim 9 , wherein the aromatic sulfonic acid is represented by the following general formula (I):

wherein Ar 3 represents an optionally substituted aromatic group; R 1 independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; Y independently represents a linking group; Z independently represents a group chosen from fluorinated alcohols, fluorinated esters, substituted or unsubstituted alkyl, C5 or higher monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a fluorinated alcohol group; a is an integer of 0 or greater; b is an integer of 1 or greater; c is an integer of 1 or greater; and a+ b+ c is at least 2 and not greater than the total number of available aromatic carbon atoms of Ar 1.

21. The method of claim 9 , wherein the aromatic acid is present in an amount of from 0.01 to 20 wt% based on total solids of the trimming composition.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Kaur Irvinder
• Liu Cong
• Rowell Kevin

Classifications

• C07C309/28

  having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton · CPC title

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• G03F7/168 Primary

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title

• G03F7/405

  Treatment with inorganic or organometallic reagents after imagewise removal · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title