Extreme ultraviolet photoresist with high-efficiency electron transfer

Patent metadata

Field	Value
Publication number	US-11809080-B2
Application number	US-202217816004-A
Country	US
Kind code	B2
Filing date	Jul 29, 2022
Priority date	Dec 15, 2016
Publication date	Nov 7, 2023
Grant date	Nov 7, 2023

Abstract

A method includes forming a photoresist layer over a substrate, wherein the photoresist layer includes a polymer, a sensitizer, and a photo-acid generator (PAG), wherein the sensitizer includes a resonance ring that includes nitrogen and at least one double bond. The method further includes performing an exposing process to the photoresist layer. The method further includes developing the photoresist layer, thereby forming a patterned photoresist layer.

First claim

What is claimed is:

1. A method, comprising:
forming a photoresist layer over a substrate, wherein the photoresist layer includes a polymer responsive to an acid, a photo-acid generator (PAG), and a sensitizer bonded to the polymer, wherein the sensitizer includes an imidazole ring and a hydroxy, wherein the hydroxy is attached to a carbon atom in the imidazole ring, wherein the carbon atom is directly bonded to a nitrogen atom in the imidazole ring, wherein the PAG includes a sulfonium cation or an iodonium cation, wherein the PAG further includes a heterocyclic ring directly bonded to the sulfonium cation or the iodonium cation, and wherein the heterocyclic ring includes one nitrogen atom and less than six carbon atoms;
performing an exposing process to the photoresist layer; and
developing the photoresist layer, thereby forming a patterned photoresist layer.

2. The method of claim 1 , wherein the heterocyclic ring is a first heterocyclic ring, wherein the PAG further includes a second heterocyclic ring different from the first heterocyclic ring directly bonded to the sulfonium cation or the iodonium cation.

3. The method of claim 2 , wherein the PAG further includes a third heterocyclic ring directly bonded to the sulfonium cation, wherein the third heterocyclic ring is different from the first heterocyclic ring and the second heterocyclic ring.

4. The method of claim 3 , wherein the first heterocyclic ring includes four carbon atoms and an oxygen atom.

5. The method of claim 3 , wherein the second heterocyclic ring includes five carbon atoms and a nitrogen atom.

6. The method of claim 3 , wherein the third heterocyclic ring has four carbon atoms and two nitrogen atoms.

7. The method of claim 6 , wherein the two nitrogen atoms are bonded by two of the four carbon atoms there between.

8. The method of claim 1 , wherein the heterocyclic ring is a first heterocyclic ring, wherein the PAG further includes a second heterocyclic ring and a third heterocyclic ring both directly bonded to the sulfonium cation, wherein the first heterocyclic ring, the second heterocyclic ring, and the third heterocyclic ring have the same structure.

9. The method of claim 1 , wherein the PAG includes a structure selected from structures (A)-(H) below:

10. The method of claim 9 , wherein the sensitizer includes a structure below:

11. A method, comprising:
forming a photoresist layer over a substrate, wherein the photoresist layer includes a polymer having an acid labile group, a photo-acid generator (PAG), a sensitizer bonded to the polymer, wherein the PAG includes a sulfonium cation and three heterocyclic rings directly bonded to the sulfonium cation, and wherein the sensitizer includes an imidazole ring fused with a pyridine ring and a hydroxyl group bonded to a carbon atom adjacent to a nitrogen atom in the imidazole ring;
performing an exposing process to the photoresist layer; and
developing the photoresist layer, thereby forming a patterned photoresist layer.

12. The method of claim 11 , wherein the sensitizer further includes a propyl group bonded to a first carbon atom, and wherein the first carbon atom and two nitrogen atoms are bonded to a second carbon atom.

13. The method of claim 12 , wherein the hydroxyl group and the propyl group are bonded to the pyridine ring.

14. The method of claim 13 , wherein the hydroxyl group and the propyl group are bonded together by four carbon atoms.

15. The method of claim 11 , wherein the sensitizer includes structured (A) and (B) below:

16. The method of claim 15 , wherein the PAG bonded to the sensitizer includes structured (C)-(J) below:

17. A method, comprising:
forming a photoresist layer over a substrate, wherein the photoresist layer includes a polymer responsive to an acid, a photo-acid generator (PAG), and a sensitizer bonded to the polymer, wherein the sensitizer includes an imidazole ring and a hydroxy bonded to a carbon atom adjacent to a nitrogen atom in the imidazole ring, wherein the PAG includes a sulfonium cation and three heterocyclic rings directly bonded to the sulfonium cation;
performing an exposing process to the photoresist layer; and
developing the photoresist layer, thereby forming a patterned photoresist layer.

18. The method of claim 17 , wherein
the imidazole ring is fused with a pyridine; and
each of the heterocyclic rings includes one nitrogen atom and less than six carbon atoms.

19. The method of claim 17 , wherein the PAG includes a structure selected from structures (A)-(H) below:

20. The method of claim 17 , wherein the sensitizer includes a structure selected from structured (I)-(J) below:

Assignees

• Taiwan Semiconductor Mfg Co Ltd

Inventors

• Lai Wei-Han
• Lin Chin-Hsiang
• Wang Chien-Wei

Classifications

• G03F7/0397 Primary

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

• C07D247/02

  having the nitrogen atoms in positions 1 and 3 · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title