IP Library › Granted Patent US 8,846,296
Granted Patent B2
US 8,846,296 · App. 13/461,960 · Granted Sep 30, 2014

Photoresist compositions

Inventors: Kuang-Jung Chen (Poughkeepsie, NY); Wu-Song Huang (Poughkeepsie, NY); Ranee Wai-Ling Kwong (Wappingers Falls, NY); Sen Liu (Highland Park, NJ); Pushkara R. Varanasi (Poughkeepsie, NY)
Assignee: International Business Machines Corporation
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Quick Facts
Patent No.
US 8,846,296
App. No.
13/461,960
Granted
Sep 30, 2014
Kind
B2
Abstract

A composition is provided. The composition includes a polymer and a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation and a second amount of acid upon exposure to a second dose of radiation. The second amount of acid is greater than the first amount of acid. The second dose is greater than the first dose. The composition includes a photosensitive base generator capable of generating a first amount of base upon exposure to the first dose and a second amount of base upon exposure to the second dose, where the first amount of base is greater than the first amount of acid and the second amount of base is less than the second amount of acid. The photosensitive base generator may include benzoin carbamates, O-carbamoylhydroxylamines, O-carbamoyloximes, aromatic sulfonamides, α-lactones, N-(2-Arylethenyl)amides, azides, amides, oximines, quaternary ammonium salts, or amineimides.

Claims (21)

1. A photoresist composition, comprising:

a polymer having a structure comprising at least one acid labile group;

a photosensitive acid generator capable of generating a first amount of acid upon exposure to a first dose of radiation, said photosensitive acid generator capable of generating a second amount of acid upon exposure to a second dose of radiation, said second amount of acid greater than said first amount of acid, said second dose of radiation greater than said first dose of radiation, wherein the photosensitive acid generator comprises (trifluoro-methylsulfonyloxy)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (MDT), N-hydroxy-naphthalimide dodecane sulfonate (DDSN), or a combination thereof; and

a photosensitive base generator capable of generating a first amount of base upon exposure to said first dose of radiation, said photosensitive base generator capable of generating a second amount of base upon exposure to said second dose of radiation, said first amount of base greater than said first amount of acid, said second amount of base less than said second amount of acid,

wherein said photosensitive base generator is selected from the group consisting of quaternary ammonium salts, and,

wherein the quaternary ammonium salts have the following structure

wherein at least two groups of groups R 3 , R 4 , R 8 , and R 9 are each independently an aryl or substituted aryl group, wherein at least one group of groups R 3 , R 4 , R 8 , and R 9 is independently an alkyl, substituted alkyl, or substituted aryl group, and wherein A − is an anion.

2. The photoresist composition of claim 1 , where at least three groups of groups R 3 , R 4 , R 8 , and R 9 are each independently an aryl or substituted aryl group.

3. The photoresist composition of claim 1 , wherein a first group and a second group of the at least two groups is a first aryl group and a second aryl group, respectively, and wherein the first aryl group and the second aryl group are either a same aryl group or a different aryl group.

4. The photoresist composition of claim 1 , wherein a first group and a second group of the at least two groups is a first substituted aryl group and a second substituted aryl group, respectively, and wherein the first substituted aryl group and the second substituted aryl group are either a same substituted aryl group or a different substituted aryl group.

5. The photoresist composition of claim 1 , wherein a first group and a second group of the at least two groups is an aryl group and a substituted aryl group, respectively.

6. The photoresist composition of claim 1 , where each group of groups R 3 , R 4 , R 8 , and R 9 is a substituted aryl group, and wherein at least two groups of groups R 3 , R 4 , R 8 , and R 9 are either a same substituted aryl group or a different substituted aryl group.

7. The photoresist composition of claim 1 , wherein a first group of at least one group is a substituted aryl group.

8. The photoresist composition of claim 1 , wherein a first group of the at least two groups is a substituted aryl group, and wherein a first group of the at least one group is an alkyl group.

9. The photoresist composition of claim 1 , wherein a first group of the at least two groups is a substituted aryl group, and wherein a first group of the at least one group is a substituted alkyl group.

10. The photoresist composition of claim 2 , wherein a first group, a second group, and a third group of the at least three groups is a first aryl group, a second aryl group, and a third aryl group, respectively, and wherein at least two groups of the first, second and third aryl groups are either a same aryl group or a different aryl group.

11. The photoresist composition of claim 2 , wherein a first group, a second group, and a third group of the at least three groups is a first aryl group, a second aryl group, and a substituted aryl group, respectively, and wherein the first aryl group and the second aryl group are either a same aryl group or a different aryl group.

12. The photoresist composition of claim 2 , wherein a first group, a second group, and a third group of the at least three groups is an aryl group, a first substituted aryl group, and a second substituted aryl group, respectively, and wherein the first substituted aryl group and the second substituted aryl group are either a same substituted aryl group or a different substituted aryl group.

13. The photoresist composition of claim 2 , wherein a first group, a second group, and a third group of the at least three groups is a first substituted aryl group, a second substituted aryl group, and a third substituted aryl group, respectively, and wherein at least two groups of the first, second and third substituted aryl groups are either a same substituted aryl group or a different substituted aryl group.

14. The photoresist composition of claim 2 , wherein a first group of the at least three groups is a substituted aryl group, and wherein a first group of the at least one group is an alkyl group.

15. The photoresist composition of claim 2 , wherein a first group of the at least three groups is a substituted aryl group, and wherein a first group of the at least one group is a substituted alkyl group.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: GLOBALFOUNDRIES U.S. INC.
Reel/Frame 056987/0001 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2020
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: GLOBALFOUNDRIES INC.
Reel/Frame 054636/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2020
From: GLOBALFOUNDRIES INC.
To: GLOBALFOUNDRIES U.S. INC.
Reel/Frame 054633/0001 →
SECURITY AGREEMENT Recorded Nov 29, 2018
From: GLOBALFOUNDRIES INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 049490/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 5, 2015
From: GLOBALFOUNDRIES U.S. 2 LLC; GLOBALFOUNDRIES U.S. INC.
To: GLOBALFOUNDRIES INC.
Reel/Frame 036779/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2015
From: INTERNATIONAL BUSINESS MACHINES CORPORATION
To: GLOBALFOUNDRIES U.S. 2 LLC
Reel/Frame 036550/0001 →
Continuity (2)
Continuation 11970761 · Jan 8, 2008
Related Publication 20120214099A1 · Aug 23, 2012