Acid generators and photoresists comprising same

Patent metadata

Field	Value
Publication number	US-9499513-B2
Application number	US-201514611768-A
Country	US
Kind code	B2
Filing date	Feb 2, 2015
Priority date	Sep 15, 2012
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

Acid generator compounds are provided that are particularly useful as photoresist composition components. Preferred acid generators include cyclic sulfonium compounds that comprise a covalently linked acid-labile group.

First claim

What is claimed is:

1. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition on a substrate, the photoresist composition comprising:
(a) a polymer; and
(b) an acid generator selected from the group consisting of:
(i) 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate;
(ii) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate;
(iii) 5-(4-(2-(1-ethylcyclopentyl oxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate; and
(iv) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 44(4R)-44(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-ylipentanoyloxy)-1, 1,2,2-tetrafluorobutane-1-sulfonate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

2. The method of claim 1 wherein the photoresist composition layer is exposed to EUV radiation.

3. The method of claim 1 wherein the photoresist composition layer is exposed to e beam radiation.

4. An acid generator that comprises a cation component selected from:

5. A photoresist composition comprising:
(a) a polymer; and
(b) an acid generator of claim 4 .

6. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 5 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

7. The method of claim 6 wherein the photoresist composition layer is exposed to EUV radiation.

8. The method of claim 6 wherein the photoresist composition layer is exposed to e beam radiation.

Assignees

• Rohm & Haas Elect Mat
• Rohm & Haas Elect Mat

Inventors

• Cameron James F
• Jain Vipul
• Labeaume Paul J
• Sung Jin Wuk
• Thackeray James W

Classifications

• C07C309/17

  containing carboxyl groups bound to the carbon skeleton · CPC title

• G03F7/16

  Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74) · CPC title

• G03F7/2059

  using a scanning corpuscular radiation beam, e.g. an electron beam · CPC title

• G03F7/0045

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title