IP Library Granted Patent US 8,039,201
Granted Patent B2
US 8,039,201 · App. 11/944,105 · Granted Oct 18, 2011

Antireflective coating composition and process thereof

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Quick Facts
Patent No.
US 8,039,201
App. No.
11/944,105
Granted
Oct 18, 2011
Kind
B2
Abstract

The present invention relates to an antireflective composition comprising a polymer, a thermal acid generator and optionally a crosslinking agent, where the polymer comprises at least one hydrophobic unit (1), at least one chromophore unit (2), at least one unit with a crosslinking site (3) and optionally a unit capable of crosslinking the polymer, where, R 1 to R 8 are independently selected from hydrogen and C 1 -C 4 alkyl, W 1 is a fully or partially fluorinated alkylene group, X is selected from F, H and OH; W 2 comprises a chromophore group, and W 3 Y comprises a crosslinking site. The invention also relates to a process for using the antireflective coating composition.

Claims (23)

1. An antireflective composition comprising a polymer, a thermal acid generator and optionally a crosslinking agent, where the polymer comprises at least one hydrophobic unit (1), at least one chromophore unit (2), at least one unit (3) where Y is hydroxyl, at least one unit (3) where Y is epoxy, and optionally a unit capable of crosslinking the polymer,

where, R 1 to R 9 are independently selected from hydrogen and C 1 -C 4 alkyl, W 1 is a fully or partially fluorinated group, X is OH; W 2 is an organic moiety comprising a chromophore group, and W 3 is an aliphatic group, further where the antireflective composition forms a film after baking for 1 minute at 200° C. with a ΔCA % in the range from about 5% to about 25%, where ΔCA % is the percentage of (CA water −CA developer )/CA water , where CA is the contact angle, CA water is the contact angle of the film in water after baking for 1 minute at 200° C. and CA developer is the contact angle of the film in a 2.38 weight % tetramethyl ammonium hydroxide aqueous solution after baking for 1 minute at 200° C. and where the film after exposure to radiation is not developable in 2.38 weight % tetramethyl ammonium hydroxide aqueous solution.

2. The antireflective composition according to claim 1 where the unit (1) has the structure,

where R 1 to R 3 are independently selected from hydrogen and C 1 -C 4 alkyl, W′ 1 is selected from a single bond, a C 1 -C 20 alkylene group, and a substituted C 1 -C 20 alkylene group.

3. The antireflective composition according to claim 1 where W 1 is a nonaromatic group.

4. The antireflective composition according to claim 1 where W 1 is a nonaromatic and nonmulticyclic alkylene group.

5. The antireflective composition according to claim 1 where the chromophore group is selected from unsubstituted phenyl and substituted phenyl.

6. The antireflective composition according to claim 1 where the chromophore group is selected from unsubstituted anthracyl and substituted anthracyl.

7. The antireflective composition according to claim 1 where W 3 is selected from C 1 -C 20 alkylene.

8. The antireflective composition according to claim 1 where the polymer further comprises an additional unit 3, where Y is selected from methylol or uril.

9. The antireflective composition according to claim 1 where the optional unit capable of crosslinking the polymer is a vinyl ester comprising a crosslinking group.

10. The antireflective composition according to claim 1 where the polymer comprises other comonomeric units.

11. The antireflective composition according to claim 1 , where the polymer comprises other comonomeric units derived from vinyl alkyl esters.

12. The antireflective composition according to claim 1 , where the antireflective composition-film forms a contact angle with water in the range of about 75° to about 95 °.

13. The antireflective composition according to claim 1 , where the antireflective composition film forms a contact angle with developer in the range of about 50° to about to about 70 °.

14. A process for manufacturing a microelectronic device, comprising;

a) providing a substrate with a first layer of an antireflective coating composition from claim 1 ;

b) coating a photoresist layer above the antireflective coating layers;

c) imagewise exposing the photoresist layer;

d) developing the photoresist layer with an aqueous alkaline developing solution.

15. The process of claim 14 , where the first antireflective coating layer has k value in the range of about 0.05 to about 1.0.

16. The process of claim 14 , where the photoresist is sensitive from about 250 nm to about 12 nm.

17. The process according to claim 14 , where the developing solution is an aqueous solution comprising a hydroxide base.

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 Sep 29, 2008
From: YAO, HUIRONG; XIANG, ZHONG; YIN, JIAN; LIU, WEIHONG
To: AZ ELECTRONIC MATERIALS USA CORP.
Reel/Frame 021606/0530 →