Photoresist compositions

• US 8,846,296 B2
• Filed: 05/02/2012
• Issued: 09/30/2014
• Est. Priority Date: 01/08/2008
• Status: Active Grant

• Current Assignee: Globalfoundries US Incorporated (GlobalFoundries, Inc.)
• Original Assignee: International Business Machines Corporation
• Inventors: Chen, Kuang-Jung, Huang, Wu-Song, Kwong, Ranee Wai-Ling, Liu, Sen, Varanasi, Pushkara R.
• Primary Examiner(s): Eoff, Anca
• Application Number:
  US13/461,960
• Publication Number:
  US 20120214099A1
• Time in Patent Office: 881 Days
• Field of Search: 430/270.1, 430/919, 430/920, 430/921, 430/923, 430/924, 430/925
• US Class Current: 430/270.1
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/038 Macromolecular compounds which are rendered insoluble or differentially wettable G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021
• CPC Class Codes: G03F 7/0382 the macromolecular compound being present in a chemically amplified negative photoresist composition
• CPC Class Codes: G03F 7/0392 the macromolecular compound being present in a chemically amplified positive photoresist composition
• CPC Class Codes: G03F 7/095 having more than one photosensitive layer G03F7/075 takes precedence
• CPC Class Codes: G03F 7/20 Exposure; Apparatus therefor photographic printing apparatus for making copies G03B27/00
• CPC Class Codes: G03F 7/2022 Multi-step exposure, e.g. hybrid; backside exposure; blanket exposure, e.g. for image reversal; edge exposure, e.g. for edge bead removal; corrective exposure
• CPC Class Codes: G03F 7/30 Imagewise removal using liquid means
• CPC Class Codes: G03F 7/38 Treatment before imagewise removal, e.g. prebaking G03F7/265 takes precedence
• CPC Class Codes: G03F 7/70466 Multiple exposures, e.g. combination of fine and coarse exposures, double patterning or multiple exposures for printing a single feature stitching G03F7/70475
• CPC Class Codes: Y10S 430/12 Nitrogen compound containing

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

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

2. The photoresist composition of claim 1, where at least three groups of groups R³, R⁴, R⁸, and R⁹ 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 R³, R⁴, R⁸, and R⁹ is a substituted aryl group, and wherein at least two groups of groups R³, R⁴, R⁸, and R⁹ 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.