IP Library Granted Patent US 11,880,134
Granted Patent B2
US 11,880,134 · App. 16/204,839 · Granted Jan 23, 2024

Salts and photoresists comprising same

Inventors: Emad Aqad (Marlborough, MA); James F. Cameron (Marlborough, MA); James W. Thackeray (Marlborough, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
G03F7/0045C07C62/06C07C309/06C07C309/10C07C309/12C07C309/16C07C309/19C07C395/00C07D345/00C07D517/00G03F7/0042G03F7/0046G03F7/0397G03F7/16G03F7/2004G03F7/26C07C2603/74
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Quick Facts
Patent No.
US 11,880,134
App. No.
16/204,839
Granted
Jan 23, 2024
Kind
B2
Abstract

New Te-salt compounds, including photoactive tellurium compounds useful for Extreme Ultraviolet Lithography.

Claims (69)

1. A photoresist composition, comprising:

a resin; and

one or more salts of Formula (I):

wherein,

R 1 , R 2 , and R 3 are each independently a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted,

wherein each R 1 is either separate or connected to R 2 and/or R 3 to form a ring,

Z comprises a counter anion comprising an inorganic group selected from SbF 6 − , BF 4 − , or B(C 6 F 5 ) 4 × , a carboxylate, or an anion of a sulfonamide, and wherein the one or more salts comprises one or more acid-labile groups.

2. The photoresist composition of claim 1 , wherein the one or more salts correspond to Formula (IIA):

wherein,

R 4 and R 5 are each independently a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a C 2-20 heteroaralkyl group, a C 2-20 fluoroheteroaralkyl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted;

each R 6 is the same or different non-hydrogen substituent;

p is an integer of 0 to 5; and

Z comprises the counter anion.

3. The photoresist composition of claim 1 , wherein the one or more salts correspond to Formula (IIB):

wherein,

each R 6 is independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH may be substituted or unsubstituted;

each p is the same or different integer of 0 to 5; and

Z comprises the counter anion.

4. The photoresist composition of claim 1 , wherein the one or more salts correspond to Formula (IIIA):

wherein:

R 8 is a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted;

R 9 and R 10 are the same or different non-hydrogen substituents;

J a single bond or a connecting group that may be selected from S, O, C═O, S═O, SO 2 , or O—C═O;

s and s′ are each independently an integer of 0, 1, 2, 3, and 4; and

Z comprises the counter anion.

5. The photoresist composition of claim 1 , wherein the photoresist composition comprises one or more acid generator compounds that are distinct from the one or more salts.

6. The photoresist composition of claim 1 , wherein the one or more salts are selected from one or more of the following:

wherein Z is the counter anion.

7. A photoresist composition, comprising:

a resin; and

one or more salts of Formula (III):

wherein,

X is a single bond or a connecting group that is S, O, C═O, S═O, SO 2 , O—C═O, carbon, or nitrogen, or oxygen that together with the depicted Te atom forms a single ring group or a multiple fused or linked ring structure;

R 7 is a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted;

each R 7′ is the same or different non-hydrogen ring substituent;

q is an integer equal to 0 to the maximum valance permitted by the ring members; and

Z comprises a counter anion comprising an inorganic group selected from SbF 6 − , BF 4 − , or B(C 6 F 5 ) 4 × , a carboxylate, or an anion of a sulfonamide,

wherein the one or more salts comprises one or more acid-labile groups.

8. A method for providing a photoresist relief image, the method comprising:

a) applying a coating layer of a photoresist composition of claim 1 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

9. The method of claim 8 , wherein the one or more salts correspond to Formula (IIA):

wherein,

R 4 and R 5 are each independently a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted;

each R 6 is the same or different non-hydrogen substituent;

p is an integer of 0 to 5; and

Z comprises the counter anion.

10. The method of claim 8 , wherein the one or more salts correspond to Formula (IIB):

wherein,

each R 6 is independently a halogen, —CN, —OH, a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 1-10 alkoxy group, a C 1-10 fluoroalkoxy group, a C 3-10 cycloalkyl group, a C 3-10 fluorocycloalkyl group, a C 3-10 cycloalkoxy group, or a C 3-10 fluorocycloalkoxy group, each of which except a halogen, —CN, and —OH may be substituted or unsubstituted;

each p is the same or different integer of 0 to 5; and

Z comprises the counter anion.

11. The method of claim 8 , wherein the one or more salts correspond to Formula (IIIA):

wherein:

R 8 is a C 6-60 aryl group, a C 6-20 fluoroaryl group, a C 1-20 heteroaryl group, a non-fluorinated C 1-20 alkyl group, a non-fluorinated C 3-20 cycloalkyl group, a C 2-20 alkenyl group, or a C 2-20 fluoroalkenyl group, each of which is substituted or unsubstituted;

R 9 and R 10 are the same or different non-hydrogen substituents;

J a single bond or a connecting group that may be selected from S, O, C═O, S═O, SO 2 , or O—C═O;

s and s′ are each independently an integer of 0, 1, 2, 3, and 4; and

Z comprises the counter anion.

12. The method of claim 8 , wherein the one or more salts are selected from one or more of the following:

wherein Z is the counter anion.

13. The method of claim 8 , wherein the photoresist composition layer is exposed to 193 nm radiation.

14. The method of claim 8 , wherein the photoresist composition layer is exposed to EUV radiation.

15. A method for providing a photoresist relief image, the method comprising:

a) applying a coating layer of a photoresist composition of claim 7 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

16. The method of claim 15 , wherein the one or more salts are selected from one or more of the following:

wherein Z is the counter anion.

17. The photoresist composition of claim 1 , wherein the composition further comprises a photodecomposable quencher having an anion of an acid having a pKa>2.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 30, 2018
From: AQAD, EMAD, MR.; CAMERON, JAMES F., MR.; THACKERAY, JAMES W., MR.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 047635/0291 →