IP Library Granted Patent US 11,287,740
Granted Patent B2
US 11,287,740 · App. 16/197,349 · Granted Mar 29, 2022

Photoresist composition and method of forming photoresist pattern

Inventors: An-Ren Zi (Hsinchu, TW); Chin-Hsiang Lin (Hsinchu, TW); Ching-Yu Chang (Yilang County, TW)
Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
G03F7/0044G03F7/038G03F7/039G03F7/16G03F7/168G03F7/2004G03F7/2037G03F7/322G03F7/40H01L21/0274
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Quick Facts
Patent No.
US 11,287,740
App. No.
16/197,349
Filed
Nov 20, 2018
Granted
Mar 29, 2022
Kind
B2
Examiner
EOFF, ANCA
Art Unit
1722
USPC
430/270.1
Abstract

A photoresist composition includes a photoresist material including metal oxide nanoparticles and a ligand, and an acid having an acid dissociation constant, pKa, of −15<pKa<4, or a base having a pKa of 40>pKa>9.

Claims (33)

1. A photoresist composition, comprising:

a photoresist material including metal oxide nanoparticles and a ligand; and

an acid having an acid dissociation constant, pKa, of −15<pKa<0.

2. The photoresist composition of claim 1 , wherein the amount of the acid ranges from 0.001 wt. % to 20 wt. % based on the total weight of the photoresist composition.

3. The photoresist composition of claim 1 , wherein the amount of metal oxide nanoparticles ranges from 1 wt. % to 10 wt. % based on the total weight of the photoresist composition.

4. The photoresist composition of claim 1 , wherein the metal oxide nanoparticles have an average particle size ranging from 1 nm to 10 nm.

5. The photoresist composition of claim 1 , wherein the metal oxide nanoparticles are selected from the group consisting of titanium dioxide, zinc oxide, zirconium dioxide, nickel oxide, cobalt oxide, manganese oxide, copper oxides, iron oxides, strontium titanate, tungsten oxides, vanadium oxides, chromium oxides, tin oxides, hafnium oxide, indium oxide, cadmium oxide, molybdenum oxide, tantalum oxides, niobium oxide, aluminum oxide, and combinations thereof.

6. The photoresist composition of claim 1 , wherein the ligand is a carboxylic acid or sulfonic acid ligand.

7. The photoresist composition of claim 1 , further comprising a polymer resin and a photoactive compound.

8. A photoresist composition, comprising:

a photoresist material including metal oxide nanoparticles and a ligand;

an acid having an acid dissociation constant, pKa, of −15<pKa<0; and

a ligand stabilizer, wherein the ligand stabilizer is selected from the group consisting of ethanedioic acid (oxalic acid), methanoic acid, 2-hydroxypropanoic acid, 2-hydroxybutanedioic acid, citric acid, uric acid, trifluoromethanesulfonic acid, benzenesulfonic acid, ethanesulfonic acid, methanesulfonic acid, maleic acid, carbonic acid, HNO 3 , H 2 SO 4 , HCl, oxoethanoic acid, 2-hydroxyethanoic acid, propanedioic acid, butanedioic acid, 3-oxobutanoic acid, hydroxylamine-O-sulfonic acid, formamidine sulfinic acid, methylsulfamic acid, sulfoacetic acid, 1,1,2,2-tetrafluoroethanesulfonic acid, 1,3-propanedisulfonic acid, nonafluorobutane-1-sulfonic acid, 5-sulfo salicylic acid, monoethanolamine, monoisopropanolamine, 2-amino-2-methyl-1-propanol, 1H-benzotriazole, 1,2,4-triazole, ammonium hydroxide, ammonium sulfamate, ammonium carbamate, and combinations thereof.

9. The photoresist composition of claim 8 , wherein the amount of the ligand stabilizer ranges from 0.001 wt. % to 20 wt. % based on the total weight of the photoresist composition.

10. The photoresist composition of claim 8 , wherein the amount of metal oxide nanoparticles ranges from 1 wt. % to 10 wt. % based on the total weight of the photoresist composition.

11. The photoresist composition of claim 8 , further comprising a polymer resin and a photoactive compound.

12. The photoresist composition of claim 11 , wherein the polymer resin includes one or more groups that will decompose when exposed to or react with bases, acids, or free radicals generated by the photoactive compound.

13. The photoresist composition of claim 12 , wherein the photoactive compound is a photoacid generator, photobase generator, or a free-radical generator.

14. The photoresist composition of claim 8 , further comprising from 0.001 wt. % to 1 wt. % of a surfactant.

15. The photoresist composition of claim 8 , wherein an amount of the ligand stabilizer ranges from 1 wt. % to 10 wt. % based on a total weight of the photoresist composition.

16. A method of forming a photoresist pattern, comprising:

forming a photoresist layer comprising a photoresist composition over a substrate;

selectively exposing the photoresist layer to actinic radiation; and

developing the photoresist layer to form a pattern in the photoresist layer;

wherein the photoresist composition includes:

metal oxide nanoparticles;

a ligand; and

an acid having an acid dissociation constant, pKa, of −15<pKa<0.

17. The method according to claim 16 , wherein the actinic radiation is extreme ultraviolet radiation.

18. The method according to claim 16 , wherein the photoresist composition further comprises a polymer resin and a photoactive compound.

19. The method according to claim 18 , wherein the polymer resin includes one or more groups that will decompose when exposed to or react with bases, acids, or free radicals generated by the photoactive compound; and

the photoactive compound is a photoacid generator, photobase generator, or a free-radical generator.

20. The method according to claim 16 , further comprising extending the pattern in the photoresist layer into the substrate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 7, 2018
From: ZI, AN-REN; LIN, CHIN-HSIANG; CHANG, CHING-YU
To: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
Reel/Frame 047703/0908 →
Continuity (2)
Provisional Application 62685677 · Jun 15, 2018
Related Publication 20190384171A1 · Dec 19, 2019
Cited By (2)
US 12,222,650 US 12,730,378