Organotin oxide hydroxide patterning compositions, precursors, and patterning

Patent metadata

Field	Value
Publication number	US-10228618-B2
Application number	US-201615291738-A
Country	US
Kind code	B2
Filing date	Oct 12, 2016
Priority date	Oct 13, 2015
Publication date	Mar 12, 2019
Grant date	Mar 12, 2019

Abstract

Organometallic precursors are described for the formation of high resolution lithography patterning coatings based on metal oxide hydroxide chemistry. The precursor compositions generally comprise ligands readily hydrolysable by water vapor or other OH source composition under modest conditions. The organometallic precursors generally comprise a radiation sensitive organo ligand to tin that can result in a coating that can be effective for high resolution patterning at relatively low radiation doses and is particularly useful for EUV patterning. The precursors compositions are readily processable under commercially suitable conditions. Solution phase processing with in situ hydrolysis or vapor based deposition can be used to form the coatings.

First claim

What is claimed is:

1. A coating solution comprising:
an organic solvent;
a first organometallic composition represented by the formula R z SnO (2−(z/2)−(x/2)) (OH) x where 0<z≤2 and 0<(z+x)≤4, by the formula R′ n SnX 4−n where n=1 or 2, or a mixture thereof, wherein R and R′ are independently hydrocarbyl groups with 1-31 carbon atoms, and X is a ligand with a hydrolysable bond to Sn or a combination thereof; and
a hydrolysable metal compound represented by the formula MX′ v , where M is a metal chosen from groups 2-16 of the periodic table of elements, v=a number from 2 to 6, and X′ is a ligand with a hydrolysable M-X bond or combination thereof.

2. The coating solution of claim 1 wherein M is Sn and v=4.

3. The coating solution of claim 2 wherein from about 2 to about 60 mole percent of the Sn is in the hydrolysable metal compound.

4. The coating solution of claim 1 having from about 0.0025M to about 1.5M tin in the solution.

5. The coating solution of claim 1 wherein X and X′ are independently selected from the group consisting of 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 and aryloxo (—OR, where R is an alkyl or aryl group with 1-10 carbon atoms), azido (—N 3 ), alkynido (—C≡CR, where R 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.

6. The coating solution of claim 1 wherein X and X′ are independently —NR 1 R 2 or —OR 3 ligands, where R 1 , R 2 and R 3 are C1-C10 alkyl or cycloalkyl groups or a combination thereof.

7. The coating solution of claim 1 wherein R or R′ is a methyl, ethyl, i-propyl, n-butyl, s-butyl or t-butyl group.

8. The coating solution of claim 1 wherein the solvent is an alcohol, an ester, or a mixture thereof.

9. A coating solution comprising:
an organic solvent;
at least about 10 mole percent relative to total metal content of a first organometallic composition represented by the formula R z SnO (2−(z/2)−(x/2)) (OH) x where 0<z≤2 and 0<(z+x)≤4, by the formula R n SnX 4−1 where n=1 or 2, or a mixture thereof, wherein R is a hydrocarbyl group with 1-31 carbon atoms and X is a ligand with a hydrolysable Sn—X bond or combination thereof; and,
at least 10 mole percent relative to total metal content of a second organometallic composition represented by the formula R′ y S n X′ 4−y where y=1 or 2, wherein R′ is a hydrocarbyl group that is different from R, and X′ is ligand with a hydrolysable Sn—X′ bond or combination thereof that is the same or different from X.

10. The coating solution of claim 9 wherein R is t-butyl and R′ is methyl.

11. The coating solution of claim 9 wherein X and X′ are independently selected from the group consisting of 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 and aryloxo (—OR, where R is an alkyl or aryl group with 1-10 carbon atoms), azido (—N 3 ), alkynido (—C≡CR, where R 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.

12. The coating solution of claim 9 having from about 0.0025M to about 1.5M tin in the solution, and wherein the solvent is an alcohol, an ester, or a mixture thereof.

13. The coating solution of claim 9 further comprising at least 10 mole percent relative to total metal content of a third organometallic composition represented by the formula R″ y SnX″ 4−y where y=1 or 2, wherein R″ is a hydrocarbyl group that is different from R and R′, and X″ is ligand with a hydrolysable Sn—X″ bond or combination thereof that is the same or different from X and/or X′.

14. The coating solution of claim 9 wherein R or R′ is a methyl, ethyl, i-propyl, n-butyl, s-butyl or t-butyl group.

Assignees

• Inpria Corp

Inventors

• Meyers Stephen T
• Anderson Jeremy T
• Cardineau Brian J
• Edson Joseph Burton
• Jiang Kai
• Keszler Douglas A
• Telecky Alan J

Classifications

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/168 Primary

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title