Anti-Reflective Coating for Photolithography and Methods of Preparation Thereof

• US 20140227538A1
• Filed: 11/12/2002
• Published: 08/14/2014
• Est. Priority Date: 06/10/1999
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Kennedy, Joseph, Iwamoto, Nancy, Nakano, Tadashi, Stuck, Jason, Baldwin, Teresa, Bedwell, William, Suedmeyer, Arlene, Hebert, Mello
• Granted Patent: US 9,069,133 B2
• Time in Patent Office: Days
• US Class Current: 428/447
• 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

Claims

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

at least one silicon-based compound;

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

at least one material modification agent, wherein the at least one material modification agent consists of at least one leveling agent, at least one amine-based pH tuning agent, at least one capping agent or a combination thereof;

at least one catalyst comprising an acid; and

at least one solvent.

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

2. (canceled)

7-8. -8. (canceled)

11-12. -12. (canceled)

16-35. -35. (canceled)

38-101. -101. (canceled)

103. (canceled)

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

at least one silicon-based compound;

at least one incorporatable absorbing compound;

at least one material modification agent, wherein the at least one material modification agent consists of at least one leveling agent, at least one amine-based adhesion promoter, at least one capping agent or a combination thereof;

at least one catalyst comprising an acid; and

at least one solvent.

3. The composition of claim 104, wherein the incorporatable absorbing compound is an organic-based compound.

4. The composition of claim 104, 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.

5. The composition of claim 104, wherein the incorporatable absorbing compound strongly absorbs light over at least an approximately 10 nm wide wavelength range at wavelengths less than 375 nm.

6. The composition of claim 4, wherein the range comprises wavelengths less than about 260 nm.

10. The composition of claim 104, 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.

13. The composition of claim 104, wherein the at least one silicon-based compound comprises at least one organosiloxane compound.

14. The composition of claim 104, wherein the at least one silicon-based compound comprises hydrogensiloxane, hydrogensilsesquioxane, organohydridosiloxane, silsesquioxane-based compounds, derivatives of silicic acid and organhydridosilsesquioxane polymers;

copolymers of hydrogensilsesquioxane and an alkoxyhydridosiloxane, hydroxyhydridosiloxane, derivatives of silicic acid or mixtures thereof.

15. The composition of claim 104, wherein the polymer is of a general formula comprising (H_0-1.0SiO_1.5-2.0)_x, where x is greater than about 4, or (H_0-1.0SiO_1.5-2.0)_n(R_0-1.0SiO_1.5-2.0)_m, where m is greater than 0, the sum of n and m is from about 4 to about 5000 and R is a C₁-C₂₀ alkyl group or a C₆-C₁₂ aryl group.

36. A coating solution comprising the composition of claim 104 and an additional solvent or a solvent mixture.

37. The coating solution of claim 36, wherein the solution is between about 0.5% and about 20% by weight incorporatable absorbing compound.

102. The composition of claim 13, wherein the organosiloxane compound comprises methylsiloxane, methylsilsesquioxane, phenylsiloxane, phenylsilsesquioxane, acrylic siloxane polymers, methylphenylsiloxane, methylphenylsilsesquioxane, silicate polymers or mixtures thereof.

105. The absorbing composition of claim 104, wherein the catalyst comprises nitric acid.

106. The absorbing composition of claim 104, wherein the at least one absorbing compound is a silicon-based compound.

107. The absorbing composition of claim 104, wherein the at least one absorbing compound is a naphthalene-based, phenanthrene-based, anthracene-based, or phenyl-based compound.

108. The absorbing composition of claim 104, 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.

109. The absorbing composition of claim 104, wherein the at least one amine-based adhesion promoter comprises an aminopropylsilane.

110. The absorbing composition of claim 109, wherein the at least one amine-based adhesion promoter comprises H₂N(CH₂)₃Si(OCH₂CH₃)₃.