Antireflective coating composition and process thereof
View Patent ↗The present invention relates to an absorbing hard mask antireflective coating composition comprising a novel polymer, where the novel polymer comprises in the backbone of the polymer four repeat units -A-, -B-, -C- and -D-, where A is repeat unit which comprises a fused aromatic ring in its backbone, B has the structure (1), C is a hydroxylbiphenyl of structure (2) and D is a derivatized fluorene of structure (3), where R 1 is C 1 -C 4 alkyl, R 2 is C 1 -C 4 alkyl, R 3 and R 4 are independently hydrogen or C 1 -C 4 alkyl, and Ar′ and Ar″ are independently phenylenic, or naphthalenic derived moieties, R 5 and R 6 are independently —OH or —(CH 2 ) n OH where n=2-4, and R 7 and R 8 are independently hydrogen or C 1 -C 4 alkyl. This invention also relates to a process for forming an image using the novel antireflective coating composition.
1. An antireflective coating composition comprising a polymer capable of being crosslinked, where the polymer comprises at least one repeat unit (A) comprising a fused aromatic unit in the polymer backbone, at least one repeat unit (B) having a structure (1), at least one repeat unit (C) comprising hydroxybiphenyl repeat unit of structure (2), and at least one repeat unit (D) comprising a fluorene repeat unit of structure (3),
where R 1 is C 1 -C 4 alkyl, R 2 is C 1 -C 4 alkyl, R 3 and R 4 are independently hydrogen or a C 1 -C 4 alkyl, Ar′ and Ar″ are independently phenylenic or naphthalenic group, R 5 and R 6 are independently —OH or —(CH 2 ) n —OH where n=2-4, and R 7 and R 8 are independently hydrogen or C 1 -C 4 alkyl; and, a solvent.
2. The composition of claim 1 , where the repeat unit A has the structure (4)
where Ar′ is a fused aromatic ring containing 2-8 aromatic rings.
3. The composition of claim 1 where the repeat unit A is
4. The composition of claim 1 , where the polymer in the composition is free of aliphatic polycyclic moieties.
5. The composition of claim 1 , where the polymer further comprises unit (6),
where Ar′ is a fused aromatic ring containing 2-8 aromatic rings.
6. The composition of claim 1 , where R 1 is methyl and R 2 is methyl.
7. The composition of claim 1 , where the fused aromatic ring has 2 to 5 aromatic rings.
8. The composition of claim 1 , where the fused aromatic ring has 3 or 4 aromatic rings.
9. The composition of claim 1 , where the composition further comprises an acid generator.
10. The composition of claim 1 where D is a 9,9′-bis(hydroxyaryl)fluorene of structure (7)
where R 3 and R 4 are independently hydrogen or a C 1 -C 4 alkyl.
11. The composition of claim 1 where D is a 9,9′-bis(hydroxyphenyl)fluorene of structure (8)
where R 3 and R 4 are independently hydrogen or C 1 -C 4 alkyl, and R 7 and R 8 are independently hydrogen or C 1 -C 4 alkyl.
12. The composition of claim 1 where D is 9,9′-bis(4-hydroxyphenyl)fluorene of structure (9)
13. The composition of claim 1 , where the composition further comprises a thermal acid generator.
14. The composition of claim 1 further comprising a second polymer.
15. The composition of claim 1 further comprising a crosslinker.
16. The composition of claim 1 further comprising a crosslinker comprising multiple functional groups selected from the group consisting of esters, ethers, alcohols olefins, methoxymethylamino, and methoxymethylphenyl.
17. The composition of claim 1 further comprising a crosslinker selected from a group consisting of 1,3-adamantane diol, 1,3,5-adamantane triol, polyfunctional reactive benzylic compounds, aminoplast crosslinkers, glycourils and powderlinks.
18. 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) optionally, providing at least a second antireflective coating layer over the first antireflective coating composition layer;
b) coating a photoresist layer above the antireflective coating layers;
c) imagewise exposing the photoresist layer with radiation;
d) developing the photoresist layer with an aqueous alkaline developing solution.
19. The process of claim 18 , where the photoresist is imageable with radiation from about 240 nm to about 12 nm.
20. The process of claim 18 , where the second antireflective coating layer comprises silicon.