IP Library Granted Patent US 9,170,494
Granted Patent B2
US 9,170,494 · App. 13/527,156 · Granted Oct 27, 2015

Antireflective compositions and methods of using same

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Quick Facts
Patent No.
US 9,170,494
App. No.
13/527,156
Granted
Oct 27, 2015
Kind
B2
Abstract

The present invention relates to a novel antireflective coating composition comprising a polymer obtained from a reaction product of at least one amino compound chosen from the group consisting of a polymer with repeat unit of structure (1), structure (2) and mixtures thereof reacted with a hydroxy compound chosen from the group consisting of structure (3), structure (4) and mixtures thereof, and, a thermal acid generator. The invention also relates to a process for using the novel composition in lithography.

Claims (32)

1. An antireflective coating composition comprising

a) a polymer obtained from a reaction product of at least one amino compound chosen from the group consisting of a polymer with a repeat unit of structure (1) reacted with a hydroxy compound of structure (3) and,

b) a thermal acid generator,

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are independently H or a C 1 -C 4 alkyl group; R 13 is a direct valence bond or a C 1 -C 6 alkylene moiety, and R 14 and R 15 are independently selected from a group consisting of a H, C 1 -C 6 alkyl moiety and a carbonyloxyalkyl moiety [—(C═O)—O—R 16 ] where R 16 is a C 1 -C 6 alkyl moiety;

n is a positive integer

and further comprising a secondary polymer bearing a fluoroalcohol group, where the secondary polymer is selected from a group consisting of polyacrylates and polyacrylics.

2. The antireflective coating composition of claim 1 , where the amino compound which is reacted has a concentration from 30 to 90 mole %, and the concentration of the hydroxyl compound which is reacted ranges from 10 to 70 mole %.

3. The antireflective coating composition of claim 1 , where structure (1) is represented by structure (5)

wherein R 1 , R 4 , R 7 , R 8 are independently H or C 1 -C 4 alkyl group.

4. The antireflective coating composition of claim 3 , where in structure (5) R 1 , R 4 , R 7 , R 8 are C 1 -C 4 alkyl group.

5. The antireflective coating composition of claim 1 where structure (3) is selected from a group consisting of

6. The antireflective coating composition of claim 1 , wherein the thermal acid generator is selected from triarylsulfonium salts, aryldialkylsulfonium salts, dialkylarylsulfonium salts diaryliodonium salts, tosylates, derivatives of benzene sulfonic acid salts, alkylammonium and ammonium salts of fluoroakylsulfonic acid, and derivatives of naphthalene sulfonic acid salts.

7. The antireflective coating composition of claim 1 , wherein refractive index value of the composition at 193 nm is below 1.65 and extinction coefficient is less than 0.3.

8. The antireflective coating composition of claim 1 , wherein refractive index value of the composition is below 1.5 and extinction coefficient k is less than 0.2 at 193 nm.

9. The antireflective coating composition of claim 1 , wherein refractive index value of the composition is in the range of 1.65 to 1.3 at 193 nm.

10. The antireflective coating composition of claim 1 , where extinction coefficient is in the range of 0.05 to 0.3.

11. A process for forming an image on a photoresist comprising:

(a) coating and baking a substrate with the anti-reflective coating composition of claim 1 ;

(b) coating and baking a layer of photoresist film on top of the anti-reflective coating;

(c) image-wise exposing the photoresist to radiation;

(d) developing an image in the photoresist; and

(e) optionally, baking the substrate after the exposing step.

12. The process of claim 11 , where the photoresist is image-wise exposed at wavelengths between 10 nm to 450 nm.

13. The process of claim 11 , where the photoresist is image-wise exposed at a wavelength of 193 nm.

14. The composition according to claim 1 where the secondary polymer is a polyacrylate type polymer having structure 7

where x=10-50 mole %, y=0-40 mole %, z=0-40 mole %, y+z=20-60 mole %, m=0-30 mole %.

15. The composition according to claim 1 where the secondary polymer is a polyacrylate type polymer having structure 8

where x=10-50 mole %, y=0-40 mole %, z=0-40 mole %, =20-60 mole %, m=0-30 mole %.

16. The composition according to claim 1 where the secondary polymer is a polyacrylate type polymer having structure 9

where x=10-50 mole %, y=0-40 mole %, z=0-40 mole %, y+z=20-60 mole %, m=0-30 mole %.

17. The composition according to claim 1 where the secondary polymer is a polyacrylate type polymer having structure 10

where x=10-50 mole %, y=0-40 mole %, z=0-40 mole %, y+z=20-60 mole %, m=0-30 mole %.

Assignments (6)
MERGER Recorded Jul 27, 2020
From: RIDGEFIELD ACQUISITION
To: AZ ELECTRONIC MATERIALS S.À R.L.
Reel/Frame 053323/0591 →
CHANGE OF LEGAL ENTITY Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS S.À R.L.
To: AZ ELECTRONIC MATERIALS GMBH
Reel/Frame 053323/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS GMBH
To: MERCK PATENT GMBH
Reel/Frame 053323/0770 →
MERGER Recorded Jul 27, 2020
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: RIDGEFIELD ACQUISITION
Reel/Frame 053324/0198 →
CHANGE OF ADDRESS Recorded Jan 12, 2017
From: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.À R.L.
Reel/Frame 041345/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2014
From: YAO, HUIRONG; LIN, GUANYANG; CHO, JOONYEON
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.
Reel/Frame 033593/0989 →