Thermal acid generators and photoresist pattern trimming compositions and methods

Patent metadata

Field	Value
Publication number	US-10241407-B2
Application number	US-201615297545-A
Country	US
Kind code	B2
Filing date	Oct 19, 2016
Priority date	Oct 31, 2015
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

Provided are ionic thermal acid generators of the following general formula (I):

wherein: Ar 1 represents an optionally substituted carbocyclic or heterocyclic aromatic group; W independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; X is a cation; Y independently represents a linking group; Z independently represents a group chosen from hydroxyl, fluorinated alcohols, esters, optionally substituted alkyl, C5 or higher optionally substituted monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a hydroxyl group; a is an integer of 0 or greater; b is an integer of 1 or greater; provided that a+b is at least 1 and not greater than the total number of available aromatic carbon atoms of the aromatic group. Also provided are photoresist pattern trimming compositions and methods of trimming a photoresist pattern using the trimming compositions. The thermal acid generators, compositions and methods find particular applicability in the manufacture of semiconductor devices.

First claim

What is claimed is:

1. An ionic thermal acid generator of the following general formula (I):

wherein: Ar 1 represents an optionally substituted carbocyclic or heterocyclic aromatic group; W independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; X is a cation; Y independently represents a linking group; Z independently represents a group chosen from hydroxyl, fluorinated alcohols, esters, optionally substituted alkyl, C5 or higher optionally substituted monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a hydroxyl group that is bonded to the aromatic group through an ester group; a is an integer of 0 or greater; b is an integer of 1 or greater; provided that a+b is at least 1 and not greater than the total number of available aromatic carbon atoms of the aromatic group.

2. The ionic thermal acid generator of claim 1 , wherein the anion comprises a plurality of hydroxyl groups.

3. The ionic thermal acid generator of claim 2 , wherein the anion comprises a plurality of hydroxyl groups bonded to the aromatic group through a respective ester group.

4. The ionic thermal acid generator of claim 1 , wherein Y independently is chosen from sulfur, optionally substituted amino groups, amides, ethers, carbonyl esters, sulfonyl esters, sulfones, sulfonamides, divalent hydrocarbon groups, and combinations thereof.

5. The ionic thermal acid generator of claim 1 , wherein the cation is a pyridine derivative.

6. A photoresist pattern trimming composition, comprising: an ionic thermal acid generator of claim 1 , a matrix polymer and a solvent.

7. The photoresist pattern trimming composition of claim 6 , wherein the solvent is an organic solvent.

8. The photoresist pattern trimming composition of claim 6 , wherein the anion comprises a plurality of hydroxyl groups.

9. The photoresist pattern trimming composition of claim 8 , wherein the anion comprises a plurality of hydroxyl groups bonded to the aromatic group through a respective ester group.

10. The photoresist pattern trimming composition of claim 6 , wherein Y independently is chosen from sulfur, optionally substituted amino groups, amides, ethers, carbonyl esters, sulfonyl esters, sulfones, sulfonamides, divalent hydrocarbon groups, and combinations thereof.

11. The photoresist pattern trimming composition of claim 6 , wherein the cation is a pyridine derivative.

12. 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 pattern trimming composition of claim 6 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.

13. The method of claim 12 , wherein the anion comprises a plurality of hydroxyl groups.

14. The method of claim 13 , wherein the anion comprises a plurality of hydroxyl groups bonded to the aromatic group through a respective ester group.

15. The method of claim 12 , wherein Y independently is chosen from sulfur, optionally substituted amino groups, amides, ethers, carbonyl esters, sulfonyl esters, sulfones, sulfonamides, divalent hydrocarbon groups, and combinations thereof.

16. The method of claim 12 , wherein the cation is a pyridine derivative.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Kaur Irvinder
• Liu Cong
• Rowell Kevin
• Pohlers Gerhard
• Li Mingqi

Classifications

• C07D213/61

  Halogen atoms or nitro radicals · CPC title

• G03F7/405

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

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• G03F7/0397 Primary

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title