Coating compositions for use with an overcoated photoresist

Patent metadata

Field	Value
Publication number	US-11762292-B2
Application number	US-201514980222-A
Country	US
Kind code	B2
Filing date	Dec 28, 2015
Priority date	Dec 30, 2014
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

Organic coating compositions, particularly antireflective coating compositions for use with an overcoated photoresist, are provided that comprise that comprise a surface agent of the Formula (I).where A and B are each independently hydrogen, optionally substituted alkyl or optionally substituted aryl; X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and n is a positive integer. Preferred coating compositions can provide improved pattern collapse margin of an overcoated photoresist layer.

First claim

What is claimed is:

1. A method for forming a photoresist relief image, comprising:
a) applying on a substrate a layer of a coating composition comprising 1) a matrix polymer that comprises polyester linkages; 2) a surface energy control agent; 3) a crosslinking agent; and 4) a thermal acid generator, wherein the coating composition does not comprise fluorine;
b) thermally treating the applied coating composition layer; and thereafter
c) applying a layer of a photoresist composition above the coating composition layer,
wherein the surface energy control agent comprises a structure corresponding to the following Formula (I):

wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer, and the surface energy control agent has a number average molecule weight of 300 to 1,000.

2. The method of claim 1 wherein the photoresist composition is imaged with activating radiation and the imaged photoresist composition layer is developed to provide a photoresist relief image.

3. The method of claim 2 wherein a developer is applied to the imaged photoresist composition layer and unexposed portions of the photoresist layer are removed by the developer.

4. The method of claim 1 wherein the coating composition comprises the surface energy control agent in an amount of 1 weight percent to 10 weight percent based on total solid content of the coating composition.

5. The method of claim 1 wherein the surface energy control agent is a poly(ethylene glycol)methyl ether.

6. The method of claim 1 wherein the matrix polymer further comprises cyanurate groups.

7. The method of claim 1 further comprising imaging the photoresist composition layer with 193 nm activating radiation.

8. The method of claim 1 further comprising imaging the photoresist composition layer with EUV radiation.

9. The method of claim 1 wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl.

10. A coated substrate comprising:
a substrate having thereon:
1) a coating composition comprising a) a matrix polymer that comprises polyester linkages; b) a surface energy control agent, c) a crosslinking agent; and d) a thermal acid generator, wherein the coating composition does not comprise fluorine; and
2) a layer of a photoresist composition above the coating composition layer, wherein the surface energy control agent comprises a structure corresponding to the following Formula (I):

wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen, and wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer, and the surface energy control agent has a number average molecular weight of 300 to 1,000.

11. The substrate of claim 10 wherein the matrix polymer further comprises cyanurate groups.

12. A coating composition for use with an overcoated photoresist composition layer, the coating composition comprising:
1) a crosslinker agent;
2) a matrix polymer comprising polyester linkages;
3) a surface energy control agent which is distinct from the matrix polymer and comprising a structure corresponding to the following Formula (I):

wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen, and wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer,
the surface energy control agent has a number average molecular weight of 300 to 1,000, and
4) a thermal acid generator.
wherein the coating composition does not comprise fluorine.

13. The coating composition of claim 12 wherein the coating composition is formulated with a solvent carrier.

14. The coating composition of claim 12 wherein the surface energy control agent is a poly(ethylene glycol)methyl ether.

15. The composition of claim 12 wherein the matrix polymer comprises cyanurate groups.

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Lee Sun-Jung
• Kang Jihoon
• Hong Dong-Je

Classifications

• G03F7/002 Primary

  using materials containing microcapsules; Preparing or processing such materials, e.g. by pressure; Devices or apparatus specially designed therefor · CPC title

• G03F7/0397 Primary

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

• A41D15/04 Primary

  Garments convertible into other articles · CPC title

• G03F7/004

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

• G03F7/11

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