IP Library › Granted Patent US 11,681,221
Granted Patent B2
US 11,681,221 · App. 16/681,610 · Granted Jun 20, 2023

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 11,681,221
App. No.
16/681,610
Granted
Jun 20, 2023
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: 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 (60)

1. A photoresist, comprising:

a core group that contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb); and

one or more ligands attached to the core group;

wherein:

the ligands each have a following structure:

represents the core group;

L″ represents a chemical that includes 1˜6 carbon atoms and H;

L′″ represents a chemical that includes 1˜6 carbon atoms and H or F; and

linker represents a chemical that links L″ and L′″ together, the linker containing —C(═O)SH, —SO 2 OH, or —SO 2 SH.

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

3. The photoresist of claim 1 , wherein the core group contains 1˜18 metal ions.

4. The photoresist of claim 1 , wherein the one or more ligands are second ligands, and wherein the core group further has one or more first ligands attached thereto, the first ligands having different chemical formulas than the second ligands.

5. The photoresist of claim 4 , wherein:

the core group includes a plurality of metal ions;

a first subset of the metal ions each has one of the first ligands attached thereto; and

a second subset of the metal ions each has one of the second ligands attached thereto.

6. The photoresist of claim 4 , wherein the one or more first ligands are attached to the core group according to chemical formulas selected from the group consisting of:

7. The photoresist of claim 4 , wherein the ligands are cleavable from the core group in response to heat.

8. The photoresist of claim 4 , wherein:

the first ligands each have a following structure:

L′ represents a chemical that includes 1˜2 carbon atoms and Hydrogen (H) or Fluorine (F); and

L represents a chemical that includes 1˜6 carbon atoms and F.

9. The photoresist of claim 8 , wherein L′ represents the chemical that includes 1˜2 carbon atoms and Fluorine (F).

10. The photoresist of claim 1 , wherein the one or more second ligands are attached to the core group according to chemical formulas selected from the group consisting of:

11. A photoresist, comprising:

a core group that contains a plurality of metal ions, the metal ions containing Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb);

a first ligand attached to a first one of the metal ions; and

a second ligand attached to a second one of the metal ions, the second ligand containing —C(═O)SH, —SO 2 OH, or —SO 2 SH;

wherein:

the first ligand has one of the following chemical formulas:

the second ligand has one of the following chemical formulas:

and

wherein the photoresist is an extreme ultraviolet (EUV) photoresist.

12. A method, comprising:

coating a photoresist material over a substrate, the photoresist material containing a core group and one or more ligands attached to the core group; and

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

wherein:

the core group contains Caesium (Cs), Barium (Ba), Lanthanum (La), Cerium (Ce), Indium (In), Silver (Ag), or Antimony (Sb);

a chemical structure of the ligands includes:

represents the core group;

L″ represents a chemical that includes 1˜6 carbon atoms and H;

L′″ represents a chemical that includes 1˜6 carbon atoms and H or F; and

linker represents a chemical that links L″ and L′″ together, wherein the linker includes —C(═O)SH, —SO 2 OH, or —SO 2 SH.

13. The method of claim 12 , further comprising: constructing the photoresist material using a solvent that is selected from the group consisting of: PGMEA (Propylene glycol methyl ether acetate), PGME (propylene glycol monomethyl ether), PGEE (1-Ethoxy-2-propanol), GBL (Gamma-Butyrolactone), CHN (Cyclohexanone), EL(Ethyl lactate), Methanol, Ethanol, Propanol, n-Butanol, Acetone, DMF (Dimethylformamide), IPA (Isopropyl alcohol), THF (Tetrahydrofuran), Methyl Isobutyl Carbinol (MIBC), nBA (n-butyl acetate), MAK (2-heptanone).

14. The method of claim 13 , wherein the core group is about 0.5%˜7% of the solvent by weight.

15. The method of claim 12 , wherein the performing the EUV lithography process comprises performing a developing process using a developer that is selected from the group consisting of: PGMEA (Propylene glycol methyl ether acetate), PGME (propylene glycol monomethyl ether), PGEE (1-Ethoxy-2-propanol), GBL (Gamma-Butyrolactone), CHN (Cyclohexanone), EL (Ethyl lactate), Methanol, Ethanol, Propanol, n-Butanol, Acetone, DMF (Dimethylformamide), IPA (Isopropyl alcohol), THF (Tetrahydrofuran), Methyl Isobutyl Carbinol (MIBC), nBA (n-butyl acetate), MAK (2-heptanone).

16. The method of claim 12 , wherein:

the one or more ligands are second ligands;

the photoresist material further includes one or more first ligands attached to the core group;

the first ligands and the second ligands have different chemical formulas;

the core group includes a plurality of metal ions;

a first subset of the metal ions each has one of the first ligands attached thereto; and

a second subset of the metal ions each has one of the second ligands attached thereto.

17. The method of claim 16 , wherein the one or more first ligands are attached to the core group according to chemical formulas selected from the group consisting of:

18. The method of claim 16 , wherein:

the first ligands each have a following structure:

L′ represents a chemical that includes 1˜2 carbon atoms and Hydrogen (H) or Fluorine (F); and

L represents a chemical that includes 1˜6 carbon atoms and F.

19. The method of claim 12 , wherein the one or more second ligands are attached to the core group according to chemical formulas selected from the group consisting of:

20. The method of claim 12 , further comprising: performing a heating process, wherein the ligands are cleaved from the core group in response to the heating process.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: ZI, AN-REN; LIU, CHEN-YU; CHANG, CHING-YU
To: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
Reel/Frame 050986/0642 →
Continuity (2)
Provisional Application 62892666 · Aug 28, 2019
Related Publication 20210063876A1 · Mar 4, 2021
Cited By (1)
US 12,210,283