IP Library › Granted Patent US 11,054,742
Granted Patent B2
US 11,054,742 · App. 16/009,795 · Granted Jul 6, 2021

EUV metallic resist performance enhancement via additives

Inventors: An-Ren Zi (Hsinchu, TW); Joy Cheng (Taoyuan, TW); Ching-Yu Chang (Yilang County, TW)
Assignee: Taiwan Semiconductor Manufacturing Co., Ltd.
G03F7/0048G03F7/0042G03F7/0045G03F7/0047
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Quick Facts
Patent No.
US 11,054,742
App. No.
16/009,795
Granted
Jul 6, 2021
Kind
B2
Abstract

A photoresist layer is formed over a wafer. The photoresist layer includes a metallic photoresist material and one or more additives. An extreme ultraviolet (EUV) lithography process is performed using the photoresist layer. The one or more additives include: a solvent having a boiling point greater than about 150 degrees Celsius, a photo acid generator, a photo base generator, a quencher, a photo de-composed base, a thermal acid generator, or a photo sensitivity cross-linker.

Claims (62)

1. A material, comprising:

a metallic photoresist material for an extreme ultraviolet (EUV) lithography; and

a solvent having a boiling point greater than about 150 degrees Celsius, wherein the solvent has a chemical formula selected from the group consisting of:

2. The material of claim 1 , further comprising a photo acid generator, wherein the photo acid generator includes a cation component and an anion component, wherein the cation component has a chemical formula selected from the group consisting of:

and wherein the anion component has a chemical formula selected from the group consisting of:

3. The material of claim 1 , further comprising a photo base generator, wherein the photo base generator has a chemical formula selected from the group consisting of:

4. The material of claim 1 , further comprising a quencher, wherein the quencher has a chemical formula selected from the group consisting of:

5. The material of claim 1 , further comprising a photo de-composed base, wherein the photo de-composed base includes a cation component and an anion component, wherein the cation component has a chemical formula selected from the group consisting of:

and wherein the anion component has a chemical selected from the group consisting of:

6. The material of claim 1 , further comprising a thermal acid generator, wherein the thermal acid generator has a chemical selected from the group consisting of:

7. The material of claim 1 , further comprising a photo sensitivity cross-linker, wherein the photo sensitivity cross-linker has a chemical selected from the group consisting of:

wherein:

FG′ represents primary amines, secondary amines, hydroxyls, amides, esters, epoxies, episulfides, or anhydrid;

W represents a carbonyl (C=0) group or a sulfonyl (SO2) group;

L 3 represents a linking group covalently bonding FG′ to a sulfo(SO 2 ) group;

L 4 is a linking group covalently bonding FG′ to W;

R 2 and R 3 each represents a carbon-containing moiety or in combination form a carbon-containing ring, provided that at least one of R 2 and R 3 or the carbon-containing ring is substituted with at least one FG′; and

R 4 , R 5 , R 6 , R 7 , and R 8 each represents: H, a halide, a substituted or unsubstituted alkyl, cycloalkyl, aryl, alkaryl, ether groups, a haloalkyl, a heteroaryl, or an alkoxyl, provided that at least one of R 4 , R 5 , R 6 , R 7 , and R 8 comprises primary amines, secondary amines, hydroxy amides, esters, epoxies, episulfides, or anhydrides.

8. A method, comprising:

forming a photoresist layer over a wafer, wherein the photoresist layer includes a metallic photoresist material and a photo acid generator; and

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

wherein the photo acid generator includes a cation component and an anion component, wherein the cation component has a chemical formula selected from the group consisting of:

and wherein the anion component has a chemical formula selected from the group consisting of:

9. The method of claim 8 , wherein the photoresist layer further includes a solvent, and wherein the solvent has a chemical formula selected from the group consisting of:

10. The method of claim 9 , wherein a concentration of the solvent in the photoresist layer is in a range between about 1% and about 20%.

11. The method of claim 8 , wherein the photoresist layer further includes a photo base generator, wherein the photo base generator has a chemical formula selected from the group consisting of:

12. The method of claim 8 , wherein the photoresist layer further includes a quencher, wherein the quencher has a chemical formula selected from the group consisting of:

13. The method of claim 8 , wherein the photoresist layer further includes a photo decomposed base, wherein the photo decomposed base includes a cation component and an anion component, wherein the cation component has a chemical formula selected from the group consisting of:

and wherein the anion component has a chemical selected from the group consisting of:

14. The method of claim 8 , wherein the photoresist layer further includes a thermal acid generator, wherein the thermal acid generator has a chemical selected from the group consisting of:

15. The method of claim 14 , wherein a concentration of the thermal acid generator has a loading that is about 1%-10% weight percentage of the photoresist layer.

16. The method of claim 8 , wherein the photoresist layer further includes a photo sensitivity cross-linker, wherein the photo sensitivity cross-linker has a chemical selected from the group consisting of:

wherein:

FG′ represents primary amines, secondary amines, hydroxyls, amides, esters, epoxies, episulfides, or anhydrid;

W represents a carbonyl (C=0) group or a sulfonyl (SO2) group;

L 3 represents a linking group covalently bonding FG′ to a sulfo(SO 2 ) group;

L 4 is a linking group covalently bonding FG′ to W;

R 2 and R 3 each represents a carbon-containing moiety or in combination form a carbon-containing ring, provided that at least one of R 2 and R 3 or the carbon-containing ring is substituted with at least one FG′; and

R 4 , R 5 , R 6 , R 7 , and R 8 each represents: H, a halide, a substituted or unsubstituted alkyl, cycloalkyl, aryl, alkaryl, ether groups, a haloalkyl, a heteroaryl, or an alkoxyl, provided that at least one of R 4 , R 5 , R 6 , R 7 , and R 8 comprises primary amines, secondary amines, hydroxy amides, esters, epoxies, episulfides, or anhydrides.

17. A method, comprising:

receiving a photoresist that contains metal; and

adding, to the photoresist, a material that includes:

a solvent having a boiling point greater than about 150 degrees Celsius, a photo acid generator, a photo base generator, a quencher, a photo de-composed base, a thermal acid generator, and a photo sensitivity cross-linker, and wherein the solvent has a chemical formula selected from the group consisting of:

18. The method of claim 17 , further comprising: performing an extreme ultraviolet (EUV) lithography process using the photoresist after the material has been added to the photoresist.

19. The method of claim 17 , wherein the photoresist has a structure that includes a core group surrounded by multiple ligands, and wherein at least some of the ligands separate from the core group as a result of aging.

20. The method of claim 17 , wherein the photo acid generator includes a cation component and an anion component, wherein the cation component has a chemical formula selected from the group consisting of:

wherein the anion component has a chemical formula selected from the group consisting of:

wherein the photo base generator has a chemical formula selected from the group consisting of:

wherein the quencher has a chemical formula selected from the group consisting of:

wherein the photo de-composed base includes a cation component and an anion component,

wherein the cation component has a chemical formula selected from the group consisting of:

and wherein the anion component has a chemical selected from the group consisting of:

wherein the thermal acid generator has a chemical selected from the group consisting of:

NH 4 +C 4 F 9 SO 3 − ,NH 4 +CF 3 SO 3 − ,

and wherein the anion component has a chemical selected from the group consisting of:

wherein:

FG′ represents primary amines, secondary amines, hydroxyls, amides, esters, epoxies, episulfides, or anhydrid;

W represents a carbonyl (C=0) group or a sulfonyl (SO2) group;

L 3 represents a linking group covalently bonding FG′ to a sulfo(SO 2 ) group;

L 4 is a linking group covalently bonding FG′ to W;

R 2 and R 3 each represents a carbon-containing moiety or in combination form a carbon-containing ring, provided that at least one of R 2 and R 3 or the carbon-containing ring is substituted with at least one FG′; and

R 4 , R 5 , R 6 , R 7 , and R 8 each represents: H, a halide, a substituted or unsubstituted alkyl, cycloalkyl, aryl, alkaryl, ether groups, a haloalkyl, a heteroaryl, or an alkoxyl, provided that at least one of R 4 , R 5 , R 6 , R 7 , and R 8 comprises primary amines, secondary amines, hydroxy amides, esters, epoxies, episulfides, or anhydrides.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2018
From: ZI, AN-REN; CHENG, JOY; CHANG, CHING-YU
To: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
Reel/Frame 046382/0470 →
Continuity (1)
Related Publication 20190384173A1 · Dec 19, 2019
Cited By (3)
US 12,253,800 US 12,360,456 US 12,578,645