IP Library Granted Patent US 8,252,503
Granted Patent B2
US 8,252,503 · App. 11/844,589 · Granted Aug 28, 2012

Photoresist compositions

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Quick Facts
Patent No.
US 8,252,503
App. No.
11/844,589
Granted
Aug 28, 2012
Kind
B2
Abstract

Photoresist compositions are disclosed.

Claims (18)

1. A photoresist composition comprising a mixture of photoacid generators and a polymer comprising,

(i) recurring units of structure (1) and (2)

where each of R 61 , R 62 , R 63 , are individually selected from hydrogen or C 1-4 alkyl; and R 64 is C 1-4 alkyl; and

(ii) one additional recurring unit of structure (10)

where each R 61 , R 62 , and R 63 , are individually selected from hydrogen or C 1-4 alkyl, further where the mixture of photoacid generators comprises at least one of a compound of formula

where R 1A , R 1B , R 2A , R 2B , R 3A , R 3B , R 4A , R 4B , R 5A , and R 5B are each independently selected from hydrogen, straight alkyl chain and branched alkyl chain, R 500 is selected from unsubstituted C 1-8 perfluoroalkyl and substituted C 1-8 perfluoroalkyl;

at least one of a compound of formula

where R 1A , R 2A , R 3A , R 4A , and R 5A , are each independently selected from hydrogen, straight alkyl chain and branched alkyl chain, R 6 and R 7 are each independently selected from aryl and aralkyl, R 500 is a selected from unsubstituted C 1-8 perfluoroalkyl and substituted C 1-8 perfluoroalkyl; and,

at least one of a compound selected from the formula

where R 1A , R 1B , R 2A , R 2B , R 3A , R 3B , R 4A , R 4B , R 5A , and R 5B are each independently selected from hydrogen, straight alkyl chain and branched alkyl chain, where Xi is selected from (Rf 1 SO 2 ) 2 N − ,

where Rf 1 is selected from perfluorinated alkyl and perfluorinated cycloalkyl, further where the composition comprises at least one base selected from substituted or unsubstituted anilines and at least one base selected from substituted or unsubstituted piperidines and substituted or unsubstituted mono- or diethanolamine.

2. The composition of claim 1 which further comprises at least one photoacid generator.

3. The composition of claim 1 wherein for the polymer, the recurring unit (i) is a mixture of the compound of formula (1) where R 61 and R 62 are hydrogen, R 63 is methyl and R 64 is ethyl and the compound of formula (2) where R 61 and R 62 are hydrogen, R 63 is methyl and R 64 is ethyl.

4. The composition of claim 1 wherein the polymer further comprises the unit

where R 61 , R 62 , and R 63 , are individually selected from hydrogen or C 1-4 alkyl.

5. A process for imaging a photoresist comprising the steps of: a) coating a substrate with the photoresist composition of claim 1 ; b) baking the substrate to substantially remove the solvent; c) image-wise exposing the photoresist coating; d) post-exposure baking the photoresist coating; and e) developing the photoresist coating with an aqueous alkaline solution.

6. A method for producing a microelectronic device by forming an image on a substrate comprising: a) providing a photoresist composition of claim 1 ; b) coating a suitable substrate with the photoresist composition of step a); and c) heat treating the coated substrate of step b) until substantially all of the photoresist solvent is removed; image-wise exposing the photoresist composition and removing the image-wise exposed areas of such composition with a suitable developer.

7. The composition of claim 1 where the polymer is selected from a group consisting of poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-2-adamantyloxymethyl methacrylate-co-hydroxy-1-adamantyl acrylate-co-α-gamma-butyrolactone methacrylate), poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-hydroxy-1-adamantyl acrylate-co-5-acryloyloxy-2,6-norbornanecarbolactone), (poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-hydroxy-1-adamantyl acrylate-co-β-gamma-butyrolactone methacrylate), poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-2-adamantyloxymethyl methacrylate-co-2-adamantyloxylmethylmethacrylate-co-hydroxy-1-adamantyl acrylate-co-α-gamma-butyrolactone methacrylate), poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-2-adamantyloxymethyl methacrylate-co-2-oxo-adamantyloxylmethylmethacrylate-co-hydroxy-1-adamantyl acrylate-co-α-gamma-butyrolactone methacrylate), and poly(2-ethyl-2-adamantyl methacrylate-co-ethylcyclopentylmethacrylate-co-2-adamantyloxymethyl methacrylate-co-methylmaveloniclactone methacrylate-hydroxy-1-adamantyl acrylate-co-α-gamma-butyrolactone methacrylate).

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2015
From: AZ ELECTRONIC MATERIALS USA CORP.
To: MERCK PATENT GMBH
Reel/Frame 034742/0206 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2008
From: CHAKRAPANI, SRINIVASAN; PADMANABAN, MUNIRATHNA; THIYAGARAJAN, MUTHIAH; KUDO, TAKANORI; RENTKIEWICZ, DAVID L.
To: AZ ELECTRONIC MATERIALS USA CORP.
Reel/Frame 021034/0136 →