Organotin clusters, solutions of organotin clusters, and application to high resolution patterning

Patent metadata

Field	Value
Publication number	US-2021347791-A1
Application number	US-202117380475-A
Country	US
Kind code	A1
Filing date	Jul 20, 2021
Priority date	Nov 20, 2017
Publication date	Nov 11, 2021
Grant date	—

Abstract

Organotin clusters are described with the formula R3Sn3(O2CR′)5−x(OH)2+x(μ3-O) with 0≤x<2; R=branched or cycloalkyl with 1 to 31 carbon atoms; R′═H or alkyl with 1 to 20 carbon atoms. Three carboxylato ligands are bridging, and two OH ligands are bridging. The remaining two carboxylato ligands are in non-bridging configurations, and the non-bridging carboxylato ligands are exchangeable in solution. Solutions of these clusters are suitable for forming radiation sensitive coatings that can be used to pattern nanometer scale structures. The radiation sensitive coatings are particularly suitable for EUV patterning.

First claim

What is claimed is:

1 . A method for synthesizing a monoalkyltin tri(alkylacetylide), the method comprising:
in an organic solvent, reacting an alkylacetylene having the formula HC≡CR″ with an alkyltin tri(dialkylamide) having the formula RSn(NR′″ 2 ) 3 to form a monoalkyltin tri(alkylacetylide) having the formula RSn(C≡CR″) 3 , wherein R, R″, and R′″ independently comprise a hydrocarbyl group having from 1 to 31 carbon atoms.

2 . The method of claim 1 wherein the hydrocarbyl group comprises an aryl, an alkenyl, a cycloalkyl, a linear alkyl, or a branched alkyl.

3 . The method of claim 1 wherein R is a methyl, ethyl, i-propyl, n-butyl, s-butyl, t-butyl, t-amyl, neopentyl group, or combination thereof.

4 . The method of claim 1 wherein R is t-butyl.

5 . The method of claim 1 wherein the alkyltin tri(dialkylamide) comprises t-butyltin tri(dimethylamide).

6 . The method of claim 1 wherein the alkylacetylene comprises phenylacetylene.

7 . The method of claim 1 wherein the organic solvent comprises hexane.

8 . The method of claim 1 wherein the alkylacetylene comprises phenylacetylene, the alkyltin tri(dialkylamide) comprises t-butyltin tri(dimethylamide), the organic solvent comprises hexane, and the monoalkyltin tri(alkylacetylide) comprises t-butyltin tri(phenylacetylide).

9 . The method of claim 1 wherein the reaction temperature is maintained below 50° C. and a vapor dialkylamine is removed from the reaction.

10 . The method of claim 1 wherein a crystalline monoalkyltin tri(alkylacetylide) is collected.

11 . A method for forming a tin cluster composition, the method comprising:
in an organic solvent, reacting a monoalkyltin tri(alkylacetylide) with a carboxylic acid and water to form a crystalline compound having the formula R 3 Sn 3 (O 2 CR′) 5−x (OH) 2+x (μ 3 -O) with 0≤x<2, wherein the carboxylic acid comprises a compound having the formula R′COOH, wherein R and R′ independently comprise a hydrocarbyl group having from 1 to 31 carbon atoms.

12 . The method of claim 11 wherein the organic solvent comprises an alcohol.

13 . The method of claim 11 wherein the organic solvent comprises ethanol.

14 . The method of claim 11 wherein the molar ratio of carboxylic acid to water is from about 3 to about 18.

15 . The method of claim 11 wherein the organic solvent comprises ethanol, wherein the monoalkyltin tri(alkylacetylide) comprises t-butyltin tri(phenylacetylide), and wherein the carboxylic acid comprises formic acid.

16 . The method of claim 11 further comprising heating a solution of the organic solvent and the monoalkyltin tri(alkylacetylide) compound of claim 1 to dissolve the compound.

17 . The method of claim 11 wherein the reacting is performed at room temperature for at least about 30 minutes to about 2 days.

18 . The method of claim 11 wherein the crystalline compound comprises radiation sensitive tire-carbon and tin-carboxylato bonds.

19 . The method of claim 11 wherein the crystalline compound comprises EUV radiation sensitive tin-carbon bonds.

20 . The method of claim 11 wherein the crystalline compound has the formula R 3 Sn 3 (O 2 CH) 5 (OH) 2 O.

Assignees

• Inpria Corp

Inventors

• Cardineau Brian J
• Meyers Stephen T
• Jiang Kai
• Earley William
• Anderson Jeremy T

Classifications

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• C07F7/2224 Primary

  Compounds having one or more tin-oxygen linkages · CPC title

• G03F7/0042

  with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence) · CPC title

• G03F7/2004

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

• G03F7/325

  Non-aqueous compositions · CPC title