Antireflective coatings for via fill and photolithography applications and methods of preparation thereof

• US 8,992,806 B2
• Filed: 08/25/2011
• Issued: 03/31/2015
• Est. Priority Date: 11/18/2003
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Li, Bo, Kennedy, Joseph, Iwamoto, Nancy, Fradkin, Mark A., Hussein, Makarem A., Goodner, Michael D., Lu, Victor, Leung, Roger
• Primary Examiner(s): Hamilton, Cynthia
• Application Number:
  US13/217,706
• Publication Number:
  US 20120001135A1
• Time in Patent Office: 1,314 Days
• Field of Search: 430/270.1, 430/273.1, 430/271.1
• US Class Current: 252/589
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: G03F 7/0751 used as adhesion-promoting additives or as means to improve adhesion
• CPC Class Codes: G03F 7/0752 in non photosensitive layers or as additives, e.g. for dry lithography
• CPC Class Codes: G03F 7/091 characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement

Abstract

An absorbing composition is described herein that includes at least one inorganic-based compound, at least one absorbing compound, and at least one material modification agent. In addition, methods of making an absorbing composition are also described that includes: a) combining at least one inorganic-based compound, at least one absorbing compound, at least one material modification agent, an acid/water mixture, and one or more solvents to form a reaction mixture; and b) allowing the reaction mixture to form the absorbing composition at room temperature. Another method of making an absorbing composition includes: a) combining at least one inorganic-based compound, at least one absorbing compound, at least one material modification agent, an acid/water mixture, and one or more solvents to form a reaction mixture; and b) heating the reaction mixture to form the absorbing composition. Yet another method of making an absorbing composition is described that includes: a) combining at least one inorganic-based compound, at least one absorbing compound, at least one material modification agent, and one or more solvents to form a reaction mixture, wherein the at least one material modification agent comprises at least one acid and water; and b) heating the reaction mixture to form an absorbing material, a coating or a film. In other methods of making an absorbing composition described herein, those methods include: a) combining at least one inorganic-based compound, at least one absorbing compound, at least one material modification agent, and one or more solvents to form a reaction mixture, wherein the at least one material modification agent comprises at least one acid and water; and b) allowing the reaction mixture to form an absorbing material, a coating or a film.

Claims

1. An absorbing composition formed from a reaction mixture comprising:

at least one inorganic compound;

at least one light absorbing compound, wherein the at least one light absorbing compound comprises anthraflavic acid, 9-anthracene carboxylic acid, 9-anthracene methanol, alizarin, quinizarin, primuline, 2-hydroxy-4(3-triethoxysilylpropoxy)-diphenylketone, rosolic acid, triethoxysilylpropyl-1,8-naphthalimide, 9-anthracene carboxy-alkyl triethoxysilane, phenyltriethoxysilane, 10-phenanthrene carboxy-methyl triethoxysilane, 4-phenylazophenol, 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane or mixtures thereof; and

at least one adhesion promoter comprising, γ

-aminopropyltriethoxysilane or a salt of γ

-aminopropyltriethoxysilane.

2. The composition of claim 1, wherein the at least one adhesion promoter comprises the salt of γ

-aminopropyltriethoxysilane, and the salt of γ

-aminopropyltriethoxysilane comprises γ

-aminopropyltriethoxysilane triflate, γ

-aminopropyltriethoxysilane methanesulfonate, γ

-aminopropyltriethoxysilane nitrate, γ

-aminopropyltriethoxysilane nonafluorobutane-1-sulfonate or a combination thereof.

3. The composition of claim 1, wherein the at least one light absorbing compound comprises 9-anthracene carboxy-alkyl triethoxysilane, phenyltriethoxysilane, 10-phenanthrene carboxy-methyl triethoxysilane, 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane or mixtures thereof.

4. The composition of claim 3, wherein the at least one light absorbing compound comprises 9-anthracene carboxy-methyl triethoxysilane.

5. The composition of claim 1, wherein the at least one light absorbing compound is chemically bonded to the at least one inorganic compound.

6. An absorbing composition comprising:

at least one inorganic compound;

at least one light absorbing compound; and

at least one adhesion promoter comprising a salt of γ

-aminopropyltriethoxysilane, wherein the salt of γ

-aminopropyltriethoxysilane comprises γ

-aminopropyltriethoxysilane triflate, γ

-aminopropyltriethoxysilane methanesulfonate, γ

-aminopropyltriethoxysilane nitrate, γ

-aminopropyltriethoxysilane nonafluorobutane-1-sulfonate or a combination thereof.

7. The composition of claim 6, wherein the at least one light absorbing compound comprises at least one benzene ring and a reactive group selected from the group consisting of hydroxyl groups, amine groups, carboxylic acid groups and substituted silyl groups.

8. The composition of claim 6, wherein the at least one inorganic compound comprises a silicon compound.

9. The composition of claim 8, wherein the silicon compound comprises a polymer.

10. The composition of claim 6, wherein the at least one inorganic compound comprises methylsiloxane, methylsilsesquioxane, phenylsiloxane, phenylsilsesquioxane, acrylic siloxane polymers, methylphenylsiloxane, methylphenylsilsesquioxane, vinyltriethoxysilane, phenyltriethoxysilane, tetraethoxysilane, carbosilane polymers, silicate polymers, silazane polymers or mixtures thereof.

11. The composition of claim 6, wherein the at least one compound comprises hydrogensiloxane polymers, hydrogensilsesquioxane polymers, organohydridosiloxane polymers, organohydridosilsesquioxane polymers, copolymers of hydrogensilsesquioxane and an alkoxyhydridosiloxane or a hydroxyhydridosiloxane, derivatives of silicic acid or mixtures thereof.

12. The composition of claim 6, wherein the composition further comprises an alkoxy or hydroxy-containing silane monomer, a vinyl-containing silane monomer, an acrylated silane monomer or a silyl hydride compound.

13. A coating solution comprising the composition of claim 6 and at least one solvent or a solvent mixture.

14. The coating solution of claim 13, wherein the at least one solvent or the solvent mixture comprises at least one alcohol, at least one ketone, propylene glycol methyl ether acetate, at least one ether, water or a combination thereof.

15. The coating solution of claim 14, wherein the at least one alcohol comprises ethanol, iso-butyl alcohol, n-propoxy propanol, cyclopentanol, iso-amyl alcohol, t-amyl alcohol, 1-octanol, 1-methoxy-2-propanol, or a combination thereof.

16. A film formed from the absorbing composition of claim 6.

17. The film of claim 16, wherein the film absorbs light at a wavelength at or less than 365 nm.

18. The composition of claim 6, wherein the at least one light absorbing compound comprises phenylsiloxane, phenylsilsesquioxane, phenyltriethoxysilane, methylphenylsiloxane, methylphenylsilsesquioxane, silicate polymers, silazane polymers or mixtures thereof.

19. The composition of claim 6, wherein the at least one light absorbing compound comprises or is formed from 9-anthracene carboxy-alkyl triethoxysilane, phenyltriethoxysilane, 10-phenanthrene carboxy-methyl triethoxysilane, 4-ethoxyphenylazobenzene-4-carboxy-methyl triethoxysilane, 4-methoxyphenylazobenzene-4-carboxy-methyl triethoxysilane or mixtures thereof.

20. The composition of claim 19, wherein the at least one light absorbing compound comprises or is formed from 9-anthracene carboxy-methyl triethoxysilane.

21. The composition of claim 6, wherein the at least one light absorbing compound is chemically bonded to the at least one inorganic compound.

22. The composition of claim 6, wherein the at least one inorganic compound is the product of the synthesis of silane reactants in the presence of an acid/water mixture.

23. The composition of claim 22, wherein the silane reactants comprise tetraethoxysilane and methyltriethoxysilane.

24. An absorbing composition formed from a reaction mixture comprising:

at least one inorganic compound,

at least one light absorbing compound,

at least one adhesion promoter comprising a salt of γ

-aminopropyltriethoxysilane, wherein the salt of γ

-aminopropyltriethoxysilane comprises γ

-aminopropyltriethoxysilane triflate, γ

-aminopropyltriethoxysilane methanesulfonate, γ

-aminopropyltriethoxysilane nitrate, γ

-aminopropyltriethoxysilane nonafluorobutane-1-sulfonate or a combination thereof.

25. The absorbing composition of claim 24, wherein the reaction mixture further comprises:

an acid/water mixture, and

at least one solvent.

26. The absorbing composition of claim 24, wherein the at least one inorganic compound comprises a silicon compound.

27. The absorbing composition of claim 24, wherein the at least one adhesion promoter comprises γ

-aminopropyltriethoxysilane triflate.