Patterned organometallic photoresists and methods of patterning
A rinse process is described for processing an initially patterned structure formed with an organometallic radiation sensitive material, in which the rinse process can remove portions of the composition remaining after pattern development to make the patterned structure more uniform such that a greater fraction of patterned structures can meet specifications. The radiation sensitive material can comprise alkyl tin oxide hydroxide compositions. The rinsing process can be effectively used to improve patterning of fine structures using extreme ultraviolet light.
1. A method for forming an adjusted patterned structure, the method comprising rinsing an initial patterned structure with a rinse solution to remove a portion of developed photoresist to control pattern dimensions and to form an adjusted patterned structure,
wherein the initial patterned structure comprises an organotin oxide hydroxide and tin residue.
2. The method of claim 1 wherein the organotin oxide hydroxide comprises an R—Sn bond, wherein R is a hydrocarbyl ligand with 1-31 carbon atoms and wherein the hydrocarbyl ligand can be linear, branched or cyclic moieties bound to the Sn at a primary, secondary, or tertiary carbon, and may optionally comprise aryl, alkenyl, alkynyl groups and/or heteroatom functional groups.
3. The method of claim 1 wherein the removed portion comprises the tin residue.
4. The method of claim 3 wherein the tin residue is associated with regions of unexposed or partially exposed developed photoresist and/or one or more microbridge defects.
5. The method of claim 4 wherein the regions of unexposed or partially exposed developed photoresist are along edges of features in the initial developed pattern.
6. The method of claim 1 wherein the rinse solution comprises aqueous quaternary ammonium hydroxide.
7. The method of claim 1 wherein the rinse solution comprises an organic solvent.
8. The method of claim 1 wherein the rinse solution is about 0.5 to 30 weight percent aqueous tetramethyl ammonium hydroxide (TMAH).
9. The method of claim 1 wherein the initial patterned structure was formed by (i) coating the surface of the substrate with an organometallic radiation sensitive resist material to form the radiation sensitive resist film, (ii) exposing the radiation sensitive resist film to patterned radiation to form an exposed film with exposed portions and unexposed portions, and (iii) contacting the exposed film with a developing solution to form a developed photoresist wherein either the exposed portions or the unexposed portions are selectively soluble in the developing solution.
10. The method of claim 9 further comprising, during coating and/or after coating, hydrolysing the organometallic radiation sensitive resist material to form the radiation sensitive resist film.
11. The method of claim 10 wherein hydrolysing is performed with water vapor.
12. The method of claim 9 wherein the organometallic radiation sensitive resist material comprises a composition represented by the formula RSnX 3 , wherein R is a hydrocarbyl ligand with 1-31 carbon atoms bound to Sn with a metal-carbon bond, and wherein X is a ligand having a hydrolysable bond with Sn.
13. The method of claim 12 wherein the hydrocarbyl ligand can be linear, branched or cyclic moieties bound to the Sn at a primary, secondary, or tertiary carbon, and may optionally comprise aryl, alkenyl, alkynyl groups and/or heteroatom functional groups.
14. The method of claim 12 wherein R is a methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, t-butyl, isobutyl, t-amyl, cyclopropropyl, cyclobutyl, cyclopentyl, benzyl, or allyl group.
15. The method of claim 12 wherein the hydrocarbyl ligand is substituted with cyano, thio, silyl, ether, keto, ester, phenyl, or halogenated groups.
16. The method of claim 12 wherein X is alkylamido or dialkylamido (—NR 1 R 2 , where R 1 and R 2 are independently hydrocarbon groups with 1-10 carbon atoms or hydrogen), siloxo (—OSiR 1 R 2 R 3 , where R 1 , R 2 , are independently hydrocarbon groups with 1-10 carbon atoms), silylamido (—N(SiR 1 3 )(R 2 ), where R 1 and R 2 are independently hydrocarbon groups with 1-10 carbon atoms), disilylamido (—N(SiR 1 3 )(SiR 2 3 ) where R 1 and R 2 are independently hydrocarbon groups with 1-10 carbon atoms), alkoxo or aryloxo (—OR 1 , where R 1 is an alkyl or aryl group with 1-10 carbon atoms), azido (—N 3 ), alkynido (—C≡CR 1 , where R 1 is a hydrocarbon group with 1-9 carbon atoms), amidato (—NR 1 (COR 2 ) where R 1 and R 2 are independently hydrocarbon groups with 1-7 carbon atoms or hydrogen), amidinato (—NR 1 C(NR 2 )R 3 ) where R 1 and R 2 are independently hydrocarbon groups with 1-8 carbon atoms or hydrogen), imido (—N(COR 1 )(COR 2 ), where R 1 and R 2 are independently hydrocarbon groups with 1-8 carbon atoms or hydrogen), or fluorinated analogues thereof, or combinations thereof.
17. The method of claim 16 wherein R 1 and/or R 2 are a methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, or t-amyl group.
18. The method of claim 16 wherein R 1 and/or R 2 are a branched alkyl group.
19. The method of claim 12 wherein X is alkylamido or dialkylamido (—NR 1 R 2 , where R 1 and R 2 are independently hydrocarbon groups with 1-10 carbon atoms or hydrogen) or wherein X is alkoxo (—OR, where R is an alkyl group with 1-10 carbon atoms).
20. The method of claim 9 wherein coating comprises spin coating, spray coating, dip coating, vapor deposition, knife edge coating, and/or printing.
21. The method of claim 9 wherein the radiation sensitive resist film comprises radiation sensitive tin-carbon bonds and/or radiation sensitive tin-carboxylate bonds.