Anti-reflective coating for photolithography and methods of preparation thereof

• US 9,069,133 B2
• Filed: 11/12/2002
• Issued: 06/30/2015
• Est. Priority Date: 06/10/1999
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Baldwin, Teresa, Kennedy, Joseph, Iwamoto, Nancy, Nakano, Tadashi, Bedwell, William, Stuck, Jason, Hebert, Mello, Suedemeyer, Arlene
• Primary Examiner(s): MOORE, MARGARET G
• Application Number:
  US10/495,686
• Publication Number:
  US 20140227538A1
• Time in Patent Office: 4,613 Days
• Field of Search: 106/287.11, 428/447
• US Class Current: 1/1
• CPC Class Codes: C03C 17/008 comprising a mixture of materials covered by two or more of the groups C03C17/02, C03C17/06, C03C17/22 and C03C17/28
• CPC Class Codes: C03C 17/30 with silicon-containing compounds
• CPC Class Codes: C08G 77/04 Polysiloxanes
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: C09D 183/06 containing silicon bound to oxygen-containing groups C09D183/12 takes precedence
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: G02B 5/23 Photochromic filters
• CPC Class Codes: G03F 7/091 characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
• CPC Class Codes: H01L 21/0276 using an anti-reflective coating anti-reflective coating for lithography in general G03F7/09
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Anti-reflective coating materials for ultraviolet photolithography include at least one absorbing compound and at least one material modification agent, such as at least one porogen, at least one high-boiling solvent, at least one capping agent, at least one leveling agent, at least one catalyst, at least one replacement solvent, at least one pH tuning agent, and/or a combination thereof that are incorporated into inorganic-based materials or inorganic compositions and/or compounds. Suitable absorbing compounds are those that absorb around wavelengths such as 365 nm, 248 nm, 193 nm and 157 nm that may be used in photolithography.

Claims

1. An absorbing composition formed from the constituents consisting of:

tetraethoxysilane (TEOS);

methyltriethoxysilane (MTEOS);

at least one incorporatable absorbing compound, wherein the incorporatable absorbing compound comprises two or more benzene rings;

at least one material modification agent comprising γ

-aminopropyltriethoxysilane (APTEOS);

at least one catalyst comprising an acid; and

at least one solvent.

6. The composition of claim 1, wherein the two or more benzene rings are fused.

2. An absorbing composition formed from the constituents consisting of:

tetraethoxysilane (TEOS);

methyltriethoxysilane (MTEOS);

at least one incorporatable absorbing compound;

γ

-aminopropyltriethoxysilane (APTEOS);

at least one catalyst comprising nitric acid, hydrochloric acid, lactic acid, acetic acid, oxalic acid, succinic acid or maleic acid; and

at least one solvent.

3. The composition of claim 2, wherein the incorporatable absorbing compound strongly absorbs light over at least an approximately 0.5 nm wide wavelength range at wavelengths less than 375 nm.

4. The composition of claim 2, wherein the incorporatable absorbing compound strongly absorbs light over at least an approximately 10 nm wide wavelength range at wavelengths less than 375 nm.

5. The composition of claim 3, wherein the range comprises wavelengths less than about 260 nm.

7. The composition of claim 2, wherein the incorporatable 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.

8. A coating solution comprising the composition of claim 2 and an additional solvent or a solvent mixture.

9. The coating solution of claim 8, wherein the solution is between about 0.5% and about 20% by weight incorporatable absorbing compound.

10. The composition of claim 2, wherein the incorporatable absorbing compound is an organic-based compound.

12. The absorbing composition of claim 2, wherein the at least one absorbing compound is a silicon-based compound.

13. The absorbing composition of claim 2, wherein the at least one absorbing compound is a naphthalene-based, phenanthrene-based, anthracene-based, or phenyl-based compound.

14. The absorbing composition of claim 2, wherein the solvent comprises isopropylalcohol, propanol, butanol, ethanol, acetone, toluene, cyclohexanone, butyrolactone, methylethylketone, methylisobutylketone, N-methylpyrrolidone, polyethyleneglycolmethylether, mesitylene, anisole, 2-heptanone, propylene glycol methyl ether acetate, at least one ether, ethyl lactate, water or a combination thereof.

15. The absorbing composition of claim 2, wherein the solvent comprises propylene glycol methyl ether acetate (PGMEA).

11. An absorbing composition formed from the constituents consisting of:

tetraethoxysilane (TEOS);

methyltriethoxysilane (MTEOS);

at least one incorporatable absorbing compound;

at least one material modification agent comprising γ

-aminopropyltriethoxysilane (APTEOS);

at least one catalyst comprising an acid, wherein the catalyst comprises nitric acid; and

at least one solvent.

16. The composition of claim 11, wherein the incorporatable absorbing compound strongly absorbs light over at least an approximately 0.5 nm wide wavelength range at wavelengths less than 375 nm.

17. The composition of claim 11, wherein the incorporatable absorbing compound strongly absorbs light over at least an approximately 10 nm wide wavelength range at wavelengths less than 375 nm.

18. The composition of claim 11, wherein the incorporatable 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.

19. The composition of claim 11, wherein the at least one absorbing compound is a silicon-based compound.

20. The composition of claim 11, wherein the at least one absorbing compound is a naphthalene-based, phenanthrene-based, anthracene-based, or phenyl based compound.