Spin-on anti-reflective coatings for photolithography

• US 8,344,088 B2
• Filed: 11/15/2001
• Issued: 01/01/2013
• Est. Priority Date: 11/15/2001
• Status: Expired due to Term

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Kennedy, Joseph T., Baldwin-Hendricks, Teresa
• Primary Examiner(s): Kelly, Cynthia
• Assistant Examiner(s): Johnson, Connie P
• Application Number:
  US10/495,688
• Publication Number:
  US 20050058929A1
• Time in Patent Office: 4,065 Days
• Field of Search: 430/270, 430/270.1, 430/272.1, 428/447, 106/287.13, 528/12, 528/23, 528/28, 528/40, 528/41, 528/43
• US Class Current: 528/31
• CPC Class Codes: C08G 77/04 Polysiloxanes
• CPC Class Codes: C09D 183/04 Polysiloxanes
• CPC Class Codes: C09D 5/006 Anti-reflective coatings
• 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: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Anti-reflective coating materials for ultraviolet photolithography include at least one absorbing compounds and at least one pH tuning agent that are incorporated into spin-on materials. 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. Suitable pH tuning agents not only adjust the pH of the final spin-on composition, but also influence the chemical performance and characteristics, mechanical performance and structural makeup of the final spin-on composition that is part of the layered material, electronic component or semiconductor component, such that the final spin-on composition is more compatible with the resist material that is coupled to it. A method of making absorbing and pH tuned spin-on materials includes combining at least one organic absorbing compound and at least one pH tuning agent with at least one silane reactant during synthesis of the spin-on materials and compositions.

Claims

1. A method of making a spin-on composition comprising:

combining at least one silane reactant, at least one incorporatable organic absorbing compound, an acid/water mixture, and one or more solvents to form a reaction mixture;

heating the reaction mixture to form the spin-on composition; and

adding at least one of the following to the spin-on composition;

an γ

-aminoalkyltrialkoxysilane, an oxide, an alkoxide, a hydrogen halide, propylene glycol methyl ether acetate, tetramethylammonium hydroxide, an amine-based oligomer and combinations thereof.

2. The method of claim 1, wherein the at least one organic absorbing compound comprises at least one benzene ring and a reactive group comprising hydroxyl groups, amine groups, carboxylic acid groups, and substituted silyl groups with silicon bonded to at least one substituent comprising alkoxy groups and halogen atoms.

3. The method of claim 1, wherein the at least one organic absorbing compound comprises an absorbing compound selected from the group consisting of 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, and mixtures thereof.

4. The method of claim 1, wherein the at least one silane reactants comprises triethoxysilane, tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, trimethoxysilane, dimethyldimethoxysilane, phenyltriethoxysilane, phenyltrimethoxysilane, diphenyldiethoxysilane, and diphenyldimethoxysilane, trichlorosilane, methyltrichlorosilane, ethyltrichlorosilane, phenyltrichlorosilane, tetrachlorosilane, chlorotriethoxysilane, chlorotrimethoxysilane, chloromethyltriethoxysilane, chloroethyltriethoxysilane, chlorophenyltriethoxysilane, chloromethyltrimethoxysilane, chloroethyltrimethoxysilane, and chlorophenyltrimethoxysilane.

5. The method of claim 1, wherein-water is also added to the spin-on composition after the step of heating the reaction mixture to form the spin-on composition.

6. The method of claim 1, wherein the acid/water mixture comprises nitric acid, lactic acid, or acetic acid.

7. A method of making a coating solution containing a spin-on material comprising:

combining at least one alkoxysilane or halosilane;

at least one incorporatable organic absorbing compounds;

an acid/water mixture, and one or more solvents to form a reaction mixture;

heating the reaction mixture to form the spin-on material; and

adding at least one of the following to the spin-on composition;

an γ

-aminoalkyltrialkoxysilane, an oxide, an alkoxide, a hydrogen halide, propylene glycol methyl ether acetate, tetramethylammonium hydroxide, an amine-based oligomer and combinations thereof.

8. The method of claim 7, further comprising adding one or more dilutant solvents to the spin-on material to produce a coating solution.