Spin-on glass anti-reflective coatings for photolithography

• US 6,268,457 B1
• Filed: 06/10/1999
• Issued: 07/31/2001
• Est. Priority Date: 06/10/1999
• Status: Expired due to Term

• Current Assignee: Alliedsignal Inc. (Honeywell International Inc.)
• Original Assignee: Alliedsignal Inc. (Honeywell International Inc.)
• Inventors: Kennedy, Joseph, Spear, Richard, Hacker, Nigel P., Baldwin, Teresa
• Primary Examiner(s): Moore, Margaret G.
• Application Number:
  US09/330,248
• Time in Patent Office: 782 Days
• Field of Search: 528/39, 528/41, 528/43, 528/10, 524/769, 524/715, 524/728, 524/765, 524/775, 524/858, 524/859, 524/719, 524/718, 106/287.13, 106/287.16
• US Class Current: 528/39
• 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: 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: 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 deep ultraviolet photolithography include one or more organic dyes incorporated into spin-on-glass materials. Suitable dyes are strongly absorbing over wavelength ranges around wavelengths less than 260 nm such as 248 nm and 193 nm, that may be used in photolithography. A method of making dyed spin-on-glass materials includes combining one or more organic dyes with alkoxysilane reactants during synthesis of the spin-on-glass materials.

Claims

1. A dyed spin-on-glass composition comprising a siloxane polymer and an incorporatable organic dye that strongly absorbs light over at least an approximately 10 nm wide wavelength range, the range at wavelengths less than about 260 nm.

2. The composition of claim 1 wherein the organic dye comprises from one to three benzene rings and a reactive group selected from the group consisting of hydroxyl groups, amine groups, carboxylic acid groups, and silicontriethoxy groups.

3. The composition of claim 2 wherein the organic dye comprises a dye 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-methyl triethoxysilane, and mixtures thereof.

4. The composition of claim 2 wherein the organic dye comprises a dye selected from the group consisting of 9-anthracene methanol, alizarin, quinizarin, 2-hydroxy-4(3-triethoxysilylpropoxy)-diphenylketone, rosolic acid, 9-anthracene carboxy-methyl triethoxysilane, and mixtures thereof.

5. The composition of claim 2 wherein the organic dye comprises 9-anthracene carboxy-methyl triethoxysilane.

6. The composition of claim 1 wherein the siloxane polymer is a polymer selected from the group consisting of methylsiloxane, methylsilsesquioxane, methylphenylsiloxane, methylphenylsilsesquioxane, and silicate polymers.

7. The composition of claim 4 wherein the siloxane polymer is a polymer selected from the group consisting of methylsiloxane, methylsilsesquioxane, methylphenylsiloxane, methylphenylsilsesquioxane, and silicate polymers.

8. A coating solution comprising the dyed spin-on-glass composition of claim 1 and a solvent.

9. The coating solution of claim 8 wherein the solution is between about 1% and about 20% by weight dyed spin-on-glass composition.

10. A method of making a dyed spin-on-glass composition comprising:

combining one or more alkoxysilanes, one or more incorporatable organic dyes, an acid/water mixture, and one or more solvents to form a reaction mixture, wherein the organic dyes strongly absorb light over at least an approximately 10 nm wide wavelength range, the range at wavelengths less than about 260 nm; and

refluxing the reaction mixture to form the dyed spin-on-glass composition.

11. The method of claim 10 wherein the one or more organic dye comprises from one to three benzene rings and a reactive group selected from the group consisting of hydroxyl groups, amine groups, carboxylic acid groups, and silicontriethoxy groups.

12. The method of claim 11 wherein the one or more organic dye comprises a dye 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-methyl triethoxysilane, and mixtures thereof.

13. The method of claim 10 wherein the one or more alkoxysilane is selected from the group consisting of tetraethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, tetramethoxysilane, methyltrimethoxysilane, phenyltriethoxysilane, and phenyltrimethoxysilane.

14. The method of claim 13 wherein the one or more alkoxysilane is tetraethoxysilane and methyltriethoxysilane.

15. The method of claim 10 wherein the acid/water mixture is a nitric acid/water mixture.

16. A method of making a dyed spin-on-glass composition comprising:

combining one or more alkoxysilanes, one or more incorporatable organic dyes, and one or more solvents to form a first reaction mixture, wherein the organic dyes strongly absorb light over at least an approximately 10 nm wide wavelength range, the range at wavelengths less than about 260 nm;

refluxing the first reaction mixture;

adding an acid/water mixture to the first reaction mixture to form a second reaction mixture.

refluxing the second reaction mixture to form the dyed spin-on-glass composition.

17. A method of making a coating solution containing a dyed spin-on-glass polymer comprising:

combining one or more alkoxysilanes, one or more incorporatable organic dyes, an acid/water mixture, and one or more solvents to form a reaction mixture, wherein the organic dyes strongly absorb light over at least an approximately 10 nm wide wavelength range, the range at wavelengths less than about 260 nm;

refluxing the reaction mixture to form a dyed spin-on-glass polymer; and

adding one or more dilutant solvents to the dyed spin-on-glass composition to produce a coating solution.

18. The method of claim 17 wherein the coating solution is between about 1% and about 20% dyed spin-on-glass polymer.