Acid generators and photoresists comprising same

Patent metadata

Field	Value
Publication number	US-2016002199-A1
Application number	US-201514611768-A
Country	US
Kind code	A1
Filing date	Feb 2, 2015
Priority date	Sep 15, 2012
Publication date	Jan 7, 2016
Grant date	—

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

1 . A photoresist composition comprising:
(a) a polymer; and (b) an acid generator that comprises a cation component selected from the group consisting of: (i) 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium; and (ii) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium.

2 . The photoresist composition of claim 1 wherein the acid generator is covalently linked to the polymer.

3 . The photoresist composition of claim 2 , wherein the acid generator comprises a polymerized unit of a monomer chosen from:
(i) 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate; and (ii) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate.

4 . A 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-ethylcyclopentyloxy)-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-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate.

5 . A method for providing a photoresist relief image, 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.

6 . The method of claim 5 wherein the photoresist composition layer is exposed to EUV radiation.

7 . The method of claim 5 wherein the photoresist composition layer is exposed to e beam radiation.

8 . An acid generator that comprises a cation component selected from the group consisting of:
(i) 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium; and (ii) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium.

9 . The acid generator of claim 8 wherein the acid generator is selected from the group consisting of:
(i) a polymerized unit of 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate; and
(ii) a polymerized unit of 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate;
(iii) 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;
(iv) 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;
(v) 5-(4-(2-(1-ethylcyclopentyloxy)-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)pentanoyl oxy)-1,1,2,2-tetrafluorobutane-1-sulfonate; and
(vi) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzorb,d1thiophenium 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.

Assignees

• Rohm & Haas Elect Mat

Inventors

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

Classifications

• 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

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• G03F7/2004

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

• C07C2103/86

  Chemistry & Metallurgy · mapped topic

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title