Hardmask compositions for resist underlayer films

Abstract

Provided herein are hardmask compositions for resist underlayer films, wherein according to some embodiments of the invention, hardmask compositions include a polymer prepared by the reaction of a compound of Formula 1

Description

Claims

1. A hardmask composition for a resist underlayer film, comprising: a polymer prepared by the reaction of a compound of Formula 1

2. The hardmask composition according to claim 1, wherein R is an alkyl or aryl group.

3. The hardmask composition according to claim 2, wherein R is phenyl.

4. The hardmask composition according to claim 1, wherein the catalyst comprises an acid or a base catalyst.

5. The hardmask composition according to claim 4, wherein the acid catalyst is selected from one or more of the group consisting of p-toluenesulfonic acid, organic acids, p-toluenesulfonic acid monohydrate, pyridinium p-toluenesulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate and alkyl esters of organic sulfonic acids.

6. The hardmask composition according to claim 4, wherein the base catalyst comprises one or more ammonium hydroxides of the formula NH4OH or N(R′)4OH, wherein R′ is a monovalent organic group.

7. The hardmask composition of claim 4, wherein the catalyst is an acid catalyst, and wherein the hardmask composition further comprises an amine base.

8. The hardmask composition of claim 7, wherein the amine base comprises one or more of a trialkyl amine and an aromatic amine comprising a pyridine ring.

9. The hardmask composition according to claim 7, wherein the amine base is present in an amount in a range of about 0.01 to about 10 parts by weight, based on the total weight of the composition.

10. The hardmask composition according to claim 4, wherein the polymer is prepared by reacting about 10 to about 90 parts by weight of the compound of Formula 1 with about 90 to about 10 parts by weight of the compound of Formula 2 in about 5 to about 70 parts by weight of the solvent, in the presence of about 0.01 to about 5 parts by weight of the acid or base catalyst, based on the total weight of the hardmask composition.

11. The hardmask composition according to claim 1, wherein the polymer is present in an amount in a range of about 1 to about 50 parts by weight, based on the total weight of the composition.

12. The hardmask composition according to claim 1, further comprising one or more of a crosslinking agent and a surfactant.

13. The hardmask composition according to claim 1, further comprising one or more of the compounds selected from the group consisting of pyridinium p-toluenesulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate and alkyl esters of organic sulfonic acids.

14. The hardmask composition according to claim 1, wherein the polymer comprises at least one structure selected from the structures represented by Formulae 6-10

15. A hardmask composition for a resist underlayer film, comprising: a polymer comprising about 10 to about 99 mol %, based on the total moles of silicon-containing monomeric units, of the monomeric unit of Formula 3 below:

16. The hardmask composition according to claim 15, wherein R, R1 and R2 are each independently an alkyl or an aryl group.

17. The hardmask composition according to claim 16, wherein R, R1 and R2 are each a phenyl group.

18. The hardmask composition according to claim 15, further comprising an amine base.

19. The hardmask composition according to claim 18, wherein the amine base comprises one or more of a trialkyl amine and an aromatic amine comprising a pyridine ring.

20. The hardmask composition according to claim 18, wherein the amine base is present in an amount in a range of about 0.01 to about 10 parts by weight, based on the total weight of the composition.

21. The hardmask composition according to claim 15, further comprising one or more of a crosslinkng agent and a surfactant.

22. The hardmask composition according to claim 15, wherein the polymer is present in an amount in a range of about 1 to about 50 parts by weight, based on the total weight of the composition.

23. The hardmask composition according to claim 15, further comprising one or more compound selected from the group consisting of pyridinium p-toluenesulfonate, 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and alkyl esters of organic sulfonic acids.

24. A method for producing a semiconductor integrated circuit device, comprising the steps of: (a) providing a material layer on a substrate;(b) forming a hardmask layer on the material layer wherein the hardmask layer is composed of an organic material;(c) forming an antireflective hardmask layer using the hardmask composition according to claim 1 for a resist underlayer film on the material layer;(d) forming a radiation-sensitive imaging layer on the antireflective hardmask layer;(e) patternwise exposing the imaging layer to radiation to form a pattern of radiation-exposed regions in the imaging layer;(f) selectively removing portions of the radiation-sensitive imaging layer and the antireflective hardmask layer to expose portions of the hardmask material layer containing an organic material;(g) selectively removing portions of the patterned antireflective hardmask layer and the hardmask material layer containing an organic material to expose portions of the material layer; and(h) etching the exposed portions of the material layer to form a patterned material layer.

25. A semiconductor integrated circuit device produced by the method according to claim 24.

26. A method for producing a semiconductor integrated circuit device, comprising the steps of: (a) providing a material layer on a substrate;(b) forming a hardmask layer on the material layer wherein the hardmask layer is composed of an organic material;(c) forming an antireflective hardmask layer using the hardmask composition according to claim 15 for a resist underlayer film on the material layer;(d) forming a radiation-sensitive imaging layer on the antireflective hardmask layer;(e) patternwise exposing the imaging layer to radiation to form a pattern of radiation-exposed regions in the imaging layer;(f) selectively removing portions of the radiation-sensitive imaging layer and the antireflective hardmask layer to expose portions of the hardmask material layer containing an organic material;(g) selectively removing portions of the patterned antireflective hardmask layer and the hardmask material layer containing an organic material to expose portions of the material layer; and(h) etching the exposed portions of the material layer to form a patterned material layer.

27. A semiconductor integrated circuit device produced by the method according to claim 26.