IP Library › Granted Patent US 12,210,283
Granted Patent B2
US 12,210,283 · App. 18/321,310 · Granted Jan 28, 2025

EUV photoresist with low-activation-energy ligands or high-developer-solubility ligands

Inventors: An-Ren Zi (Hsinchu, TW); Chen-Yu Liu (Kaohsiung, TW); Ching-Yu Chang (Yilang County, TW)
Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
G03F7/0046G03F7/16G03F7/2004G03F7/32H01L21/0274
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Quick Facts
Patent No.
US 12,210,283
App. No.
18/321,310
Granted
Jan 28, 2025
Kind
B2
Abstract

A photoresist includes a core group that contains metal, and one or more first ligands or one or more second ligands attached to the core group. The first ligands each have a following structure: The second ligands each have a following structure: {circle around (M)} represents the core group. L′ represents a chemical that includes 0-2 carbon atoms saturated by Hydrogen (H) or Fluorine (F). L represents a chemical that includes 1-6 carbon atoms saturated by H or F. L″ represents a chemical that includes 1-6 carbon atoms saturated by H. L″′ represents a chemical that includes 1-6 carbon atoms saturated by H or F. Linker represents a chemical that links L″ and L″′ together.

Claims (66)

1. A photoresist, comprising:

a metal-containing component; and

one or more ligands coupled to the metal-containing component;

wherein each ligand in a subset of the one or more ligands includes:

a first chemical coupled to the metal-containing component, wherein the first chemical includes carbon and hydrogen;

a second chemical that includes carbon, wherein the second chemical further includes hydrogen or fluorine; and

a linker that is linked to both the first chemical and the second chemical, wherein the linker includes:

a first compound that contains —C(═O)SH; or

a second compound that contains —SO 2 OH, or —SO 2 SH.

2. The photoresist of claim 1 , wherein the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb).

3. The photoresist of claim 1 , wherein the photoresist is an extreme ultraviolet (EUV) lithography photoresist.

4. The photoresist of claim 1 , wherein:

the subset of the one or more ligands is a first subset of the ligands;

the one or more ligands further includes a second subset;

each ligand in the second subset of the ligands includes the first chemical and the second chemical; and

the first chemical and the second chemical are coupled together without the linker.

5. The photoresist of claim 4 , wherein the metal-containing component is simultaneously attached to a first ligand from the first subset and a second ligand from the second subset.

6. The photoresist of claim 5 , wherein:

the metal-containing component includes a first metal ion and a second metal ion;

the first ligand is attached directly to the first metal ion; and

the second ligand is attached directly to the second metal ion.

7. The photoresist of claim 4 , wherein the ligands in the first subset have one of the following chemical formulas:

wherein {circle around (M)} represents the metal-containing component.

8. The photoresist of claim 4 , wherein the ligands in the second subset have one of the following chemical formulas:

wherein {circle around (M)} represents the metal-containing component.

9. A photoresist, comprising

a metal-containing component;

one or more ligands attached to the metal-containing component;

wherein each ligand in a subset of the one or more ligands has one of the following chemical formulas:

wherein represents the metal-containing component; and

a linker that includes:

a first compound that contains —C(═O)SH: or

a second compound that contains —SO 2 OH, or —SO 2 SH.

10. The photoresist of claim 9 , wherein: the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Tin (Sn), Silver (Ag), or Antimony (Sb).

11. The photoresist of claim 9 , wherein:

the metal-containing component contains a plurality of metal ions;

the one or more ligands belong to a first subset of ligands that are attached to a first one of the metal ions;

the photoresist further includes a second subset of ligands that are attached to a second one of the metal ions; and

the second subset of ligands each have one of the following chemical formulas:

12. The photoresist of claim 9 , wherein the photoresist is an extreme ultraviolet (EUV) lithography photoresist.

13. A method, comprising:

forming a photoresist material over a substrate, wherein the photoresist material contains a metal-containing component and one or more ligands coupled to the metal-containing component; and

performing an extreme ultraviolet (EUV) lithography process using the photoresist material;

wherein each ligand in a subset of the one or more ligands includes:

a first chemical coupled to the metal-containing component, wherein the first chemical includes carbon and hydrogen;

a second chemical that includes carbon, wherein the second chemical further includes hydrogen or fluorine; and

a linker that is linked to both the first chemical and the second chemical, wherein the linker includes:

a first compound that contains —C(═O)SH; or

a second compound that contains —SO 2 OH, or —SO 2 SH.

14. The method of claim 13 , wherein the metal-containing component contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb).

15. The method of claim 13 , wherein:

the subset of the one or more ligands is a first subset of the ligands;

the one or more ligands further includes a second subset;

each ligand in the second subset of the ligands includes the first chemical and the second chemical; and

the first chemical and the second chemical are coupled together without the linker.

16. The method of claim 15 , wherein:

the metal-containing component is simultaneously attached to a first ligand from the first subset and a second ligand from the second subset;

the metal-containing component includes a first metal ion and a second metal ion;

the first ligand is attached directly to the first metal ion; and

the second ligand is attached directly to the second metal ion.

17. The method of claim 15 , wherein the ligands in the first subset have one of the following chemical formulas:

wherein {circle around (M)} represents the metal-containing component.

18. The method of claim 15 , wherein the ligands in the second subset have one of the following chemical formulas:

wherein {circle around (M)} represents the metal-containing component.

19. The method of claim 13 , wherein the EUV process includes an exposure process, and wherein the one or more ligands are cleaved from the metal-containing component after the exposure process.

20. The method of claim 13 , further comprising cleaving the one or more ligands from the metal-containing component at least in part via a heat treatment process.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2023
From: ZI, AN-REN; LIU, CHEN-YU; CHANG, CHING-YU
To: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
Reel/Frame 063716/0922 →
Continuity (3)
Continuation 16681610 · Nov 12, 2019
Provisional Application 62892666 · Aug 28, 2019
Related Publication 20230305396A1 · Sep 28, 2023
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