IP Library Granted Patent US 9,274,426
Granted Patent B2
US 9,274,426 · App. 14/295,656 · Granted Mar 1, 2016

Antireflective coating compositions and processes thereof

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Quick Facts
Patent No.
US 9,274,426
App. No.
14/295,656
Granted
Mar 1, 2016
Kind
B2
Abstract

The present invention relates to a novel absorbing antireflective coating composition comprising a novel crosslinkable polymer comprising at least one repeat unit (A) having structure (1), at least one repeat unit (B) having a structure (2), and at least one repeat unit (C) having structure (3) where D is a direct valence bound or C(R 1 )(R 2 ) methylene moiety where R 1 and R 2 are independently H, C 1 -C 8 alkyl, C 3 -C 24 cycloalkyl or C 6 -C 24 aryl; Ar i , Ar ii , Ar iii and Ar iv are independently phenylenic and naphthalenic moiety, R 3 and R 4 are independently hydrogen or C 1 -C 8 alkyl; and R 5 and R 6 are independently hydrogen or C 1 -C 8 alkyl; and a solvent. The invention also relates to a process for forming an image using the novel antireflective coating composition.

Claims (31)

1. An antireflective coating composition comprising

i) a crosslinkable polymer comprising at least one repeat unit (A) having structure (1), at least one repeat unit (B) having a structure (2), and at least one repeat unit (C) having structure (3)

where D is a direct valence bond or a C(R 1 )(R 2 ) methylene moiety where R 1 and R 2 are independently H, C 1 -C 8 alkyl, C 3 -C 24 cycloalkyl or C 6 -C 24 aryl; Ar i , A ii , A iii and Ar iv are independently phenylenic or naphthalenic moiety, R 3 and R 4 are independently hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy; R 5 and R 6 are independently hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy; and,

ii) a solvent.

2. The composition of claim 1 , where repeat unit A has structure (1b) where R 1 and R 2 are independently H, C 1 -C 8 alkyl, C 3 -C 24 cycloalkyl or C 6 -C 24 aryl,

3. The composition of claim 1 , where repeat unit A has structure (4) structure where R 7 is C 6 -C 24 aryl

4. The composition of claim 1 where the repeat unit B has structure (6)

where R 3 and R 4 are independently hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy.

5. The composition of claim 1 where the repeat unit C has structure (8)

where R 5 and R 6 are independently hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy.

6. The composition of claim 1 , where the repeat unit A has structure structure 5a,

7. The composition of claim 1 , where the repeat unit B has structure (7),

8. The composition of claim 1 , where the repeat unit C has structure (9),

9. The composition of claim 1 , where the composition further comprises a photo acid generator.

10. The composition of claim 1 the antireflective coating further comprises a thermal acid generator.

11. The composition of claim 1 , where the thermal acid generator chosen from ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium salts of strong non nucleophilic acids.

12. The composition of claim 1 further comprising a crosslinker.

13. The composition of claim 12 where the crosslinker is a crosslinker comprising multiple functional groups selected from the group consisting of esters, ethers, alcohols, olefins, methoxymethylamino, and methoxymethylphenyl.

14. The composition of claim 12 where the crosslinker is selected from a group consisting of 1,3-adamantane diol, 1,3,5-adamantane triol, polyfunctional reactive benzylic compounds, aminoplast crosslinkers, glycolurils and

15. The composition of claim 1 further comprising a monomer of structure 1a

where D is a direct valence bond or C(R 1 )(R 2 ) methylene moiety and where R 1 and R 2 are independently H, C 1 -C 8 alkyl, C 3 -C 24 cycloalkyl or C 6 -C 24 aryl.

16. A process for forming an image, comprising;

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

b) optionally, providing at least a second antireflective coating layer over the first antireflective coating composition layer;

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

d) imagewise exposing the photoresist layer with radiation;

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

17. The process of claim 16 , where the photoresist is imageable with radiation from about 240 nm to about 12 nm.

18. The process of claim 16 , where the second antireflective coating layer comprises silicon.

19. The process of claim 16 , where the substrate is subjected to a single post applied bake between about 90° C. to about 500° C. after providing the substrate with the first layer of the antireflective coating composition.

20. The process of claim 19 , where the substrate is subjected to a second post applied bake between 230° C. to about 450° C. after the single post applied bake.

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: RAHMAN, M. DALIL; KUDO, TAKANORI; DIOSES, ALBERTO D.; MCKENZIE, DOUGLAS; ANYADIEGWU, CLEMENT; PADMANABAN, MUNIRATHNA; MULLEN, SALEM K.
To: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.
Reel/Frame 033590/0938 →