# US 11,897,906 B2 · Monoalkyl tin compounds with low polyalkyl contamination, their compositions and methods

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- Number: US 11,897,906 B2
- Document ID: US11897906B2
- Status: Granted
- Kind: B2
- Application number: 17/198,669
- Filed: 2021-03-11
- Published: 2021-07-01
- Granted: 2024-02-13
- Earliest claimed: 2018-04-11
- Assignees: Inpria Corporation
- Applicants: Inpria Corporation
- Inventors: Joseph B. Edson; Thomas J. Lamkin; William Earley; Truman Wambach; Jeremy T. Anderson
- Web page: https://patentgrep.com/patent/US11897906B2

## CPC

- C07F 7/2284: {Compounds with one or more Sn-N linkages}
- C07F 7/2224: {Compounds having one or more tin-oxygen linkages}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

A pure composition comprises a monoalkyltin trialkoxide compound represented by the chemical formula RSn(OR′)3 or a monoalkyl tin triamide compound represented by the chemical formula RSn(NR′2)3 and no more than 4 mole % dialkyltin compounds relative to the total tin amount, where R is a hydrocarbyl group with 1-31 carbon atoms, and wherein R′ is a hydrocarbyl group with 1-10 carbon atoms. Methods are described for the formation of the pure compositions. A solid composition comprises a monoalkyl triamido tin compound represented by the chemical formula RSn—(NR′COR″)3, where R is a hydrocarbyl group with 1-31 carbon atoms, and where R′ and R″ are independently a hydrocarbyl group with 1-10 carbon atoms. The compositions are suitable for the formation of resist compositions suitable for EUV patterning in which the compositions have a high EUV absorption.

## Claims

### Claim 1

A high purity liquid composition comprising a mixture of a compound represented by the formula (CH2)5CHSn(N(CH3)2)3 and no more than 4 mole % dialkyltin compounds as an impurity relative to the total tin amount.

### Claim 2 (depends on 1)

The composition according to claim 1 further comprising one or more alkyl-tin compounds with a different alkyl ligand relative to the cyclohexyl compound and no more than 4 mole % dialkyltin compounds as an impurity relative to the total tin amount.

### Claim 3 (depends on 2)

The composition of claim 2 wherein the different alkyl ligand is methyl, ethyl, tert-butyl, tert-amyl, or a combination thereof.

### Claim 4 (depends on 1)

A solution comprising an organic solvent and the high purity liquid composition according to claim 1.

### Claim 5 (depends on 4)

The solution of claim 4 having a concentration of the compound represented by the formula (CH2)5CHSn(N(CH3)2)3 of from about 0.01M to about 2M.

### Claim 6 (depends on 4)

The solution of claim 4 wherein the organic solvent comprises an alkane, an aromatic hydrocarbon, an ether, an alcohol, or a mixture thereof.

### Claim 7 (depends on 4)

The solution of claim 4 further comprising RSnO(3/2-x/2)(OH)x (0<x<3), where R is an alkyl, cycloalkyl, branched alkyl, or substituted alkyl moiety having from 1 to 31 carbon atoms.

### Claim 8 (depends on 1)

A method to selectively form a monoalkyltin trialkoxide compound with low dialkyl tin contamination, the method comprising,
reacting a (CH2)5CHSn(N(CH3)2)3 compound with an alcohol represented by the formula HOR″ in an organic solvent to form (CH2)5CHSn(OR″)3, wherein the (CH2)5CHSn(N(CH3)2)3 reagent comprises the high purity liquid composition according to claim 1, wherein R″ is a hydrocarbyl group with 1-10 carbon atoms.

### Claim 9 (depends on 8)

The method of claim 8 wherein the reaction is performed with a tetradentate chelating agent in an amount from about 0.5 mole % to about 15 mole % relative to the tin molar quantity.

### Claim 10 (depends on 8)

A solution comprising an organic solvent and the (CH2)5CHSn(OR″)3 prepared according to the method of claim 8.

### Claim 11 (depends on 10)

The solution of claim 10 having a concentration of from about 0.01M to about 2M and wherein the solvent comprises an alcohol.