Ionic thermal acid generators for low temperature applications

Patent metadata

Field	Value
Publication number	US-9541834-B2
Application number	US-201213691689-A
Country	US
Kind code	B2
Filing date	Nov 30, 2012
Priority date	Nov 30, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

New ionic thermal acid generator compounds are provided. Also provided are photoresist compositions, antireflective coating compositions, and chemical trim overcoat compositions, and methods of using the compositions.

First claim

What is claimed is:

1. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a chemically amplified photoresist composition on a substrate;
b) exposing the photoresist layer to activating radiation and developing the exposed photoresist layer to provide a photoresist relief image;
c) applying over the exposed photoresist composition coating layer a coating layer of a chemical trim overcoat composition comprising a thermal acid generator of formula (I);
(A − )(BH) +   (I)

in which
A − is the anion of an organic or inorganic acid having a pKa of not more than 3; and
(BH) + is the monoprotonated form of a nitrogen-containing base B having a pKa between 0 and 5.0, and a boiling point less than 170° C.;
d) heating the chemical trim overcoat composition layer; and
e) developing the photoresist layer to provide a photoresist relief image.

2. The method of claim 1 wherein B is selected from the group consisting of:

in which Y is methyl or ethyl.

3. The method of claim 1 wherein B is substituted pyridine.

4. The method of claim 1 wherein A − is the anion of a fluoroalkylsulfonic acid.

5. The method of claim 1 wherein the thermal acid generator is selected from among:
3-Fluoropyridinium perfluorobutanesulfonate;
3-Fluoropyridinium triflate; and
3-Fluoropyridinium p-toluenesulfonate.

6. A coated substrate comprising:
a photoresist layer; and
over the photoresist layer, a chemical trim overcoat layer comprising an ionic thermal acid generator of formula (I)
(A − )(BH) +   (I)

in which
A − is the anion of an organic or inorganic acid having a pKa of not more than 3; and
(BH) + is the monoprotonated form of a nitrogen-containing base B having a pKa between 0 and 5.0, and a boiling point less than 170° C.

7. The substrate of claim 6 wherein B is selected from the group consisting of:

in which Y is methyl or ethyl.

8. The substrate of claim 6 wherein B is substituted pyridine.

9. The substrate of claim 6 wherein A − is the anion of a fluoroalkylsulfonic acid.

10. The substrate of claim 6 wherein the thermal acid generator is selected from among:
3-Fluoropyridinium perfluorobutanesulfonate;
3-Fluoropyridinium triflate; and
3-Fluoropyridinium p-toluenesulfonate.

11. A coated substrate comprising: an antireflective composition layer comprising a thermal acid generator of formula (I):
(A) − (BH) +   (I)

in which A − is the anion of an organic or inorganic acid having a pKa of not more than 3; and (BH) + is the monoprotonated form of a nitrogen-containing base B having a pKa between 0 and 5.0, and a boiling point less than 170° C.;
and over the antireflective coating composition layer, a photoresist composition layer, wherein B is selected from the group consisting of:

and substituted pyridine,
in which Y is methyl or ethyl.

12. The substrate of claim 11 wherein B is substituted pyridine.

13. The substrate of claim 11 wherein A − is the anion of a fluoroalkylsulfonic acid.

14. The substrate of claim 11 wherein the thermal acid generator is selected from among:
3-Fluoropyridinium perfluorobutanesulfonate;
3-Fluoropyridinium triflate; and
3-Fluoropyridinium p-toluenesulfonate.

15. A thermal acid generator represented by the formula:
(A − )(BH) +
in which
A − is the anion of a fluoroalkylsulfonic acid or inorganic acid having a pKa of not more than 3; and
(BH) + is the monoprotonated form of a nitrogen-containing base B having a pKa between 0 and 5.0, and a boiling point less than 170° C., and
wherein B is selected from the group consisting of:

in which Y is methyl or ethyl.

16. The thermal acid generator of claim 15 , wherein A − is the anion of a fluoroalkylsulfonic acid.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Pohlers Gerhard
• Liu Cong
• Xu Cheng-Bai
• Rowell Kevin
• Kaur Irvinder

Classifications

• G03F7/30

  Imagewise removal using liquid means · CPC title

• C07D277/22

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

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• C07C309/03

  of an acyclic saturated carbon skeleton · CPC title

• G03F7/091

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title