High purity monoorgano tin compounds and methods for preparation thereof

Patent metadata

Field	Value
Publication number	US-2025154178-A1
Application number	US-202418934327-A
Country	US
Kind code	A1
Filing date	Nov 1, 2024
Priority date	Nov 15, 2023
Publication date	May 15, 2025
Grant date	—

Abstract

Monoorgano tin compounds having chemical formula R′SnX 3 and high purity are described. R′ is an optionally substituted hydrocarbyl group, X is selected from NR 2 and OR, and each R is independently a linear or branched alkyl group having about 1 to about 10 carbon atoms. Methods for synthesizing and purifying these compounds are also provided. The monoorgano tin compounds may be used for the formation of high-resolution EUV lithography patterning precursors and are attractive due to their high purity and minimal concentration of diorgano tin impurities.

First claim

We claim:

1 . A monoorgano tin compound having formula (1) having a purity of at least about 95 mol % and containing less than about 5 mol % of a diorgano tin compound having formula (2):
R′SnX 3   (1)
R′ 2 SnX 2   (2)

wherein R′ has formula [I] or [II], and X is selected from NR 2 and OR, wherein each R is independently a linear or branched alkyl group having about 1 to about 10 carbon atoms which is optionally substituted with one or more halogen atoms;
[I] CRaRbRc, wherein Ra is an aromatic ring having about 3 to about 10 carbon atoms which is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms, Rb and Rc are each independently hydrogen or a hydrocarbyl substituent having about 1 to about 10 carbon atoms, wherein each hydrocarbyl substituent is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms;
[II] CR A R B R C , wherein R A is (CH 2 ) n OR E , n is 0, 1, or 2, R E is a saturated hydrocarbon group having 1 to about 10 carbon atoms, R B and R C are each independently hydrogen or a saturated hydrocarbon group having about 1 to about 10 carbon atoms, wherein R′ contains about 2 to about 20 carbon atoms, wherein R A and one of R B and R C optionally form a 3 to 8-membered ring containing an ether linkage.

2 . The monoorgano tin compound according to claim 1 , wherein a content of a compound having formula (5) is less than about 5 mol %:
SnX 4   (5).

3 . The monoorgano tin compound according to claim 1 , wherein R′ is selected from the group consisting of:

wherein each A substituent is independently hydrogen, a halogen, or a hydrocarbyl substituent having about 1 to about 5 carbon atoms which is optionally substituted with one or more oxygen, halogen, or nitrogen atoms; and wherein Rx, Ry, and Rz are each independently a halogen or a hydrocarbyl substituent having about 1 to about 5 carbon atoms which is optionally substituted with one or more oxygen or nitrogen atoms, or

4 . The monoorganotin compound according to claim 1 , wherein the carbon atom in R′ bonded to tin is a secondary or tertiary carbon.

5 . The monoorganotin compound according to claim 1 , wherein Ra is a phenyl group.

6 . The monoorganotin compound according to claim 1 , wherein R A in R′ is OR E and wherein R E and at least one of R B and R C optionally form a 3 to 8-membered ring containing an ether linkage.

7 . The monoorganotin compound according to claim 1 , wherein R E is a methyl group.

8 . The monoorgano tin compound according to claim 1 , wherein X═NMe 2 .

9 . A method of synthesizing a monoorgano tin compound having formula (1) having a purity of at least about 95 mol % and containing less than about 5 mol % of a diorgano tin compound having formula (2):
R′SnX 3   (1)
R′ 2 SnX 2   (2)
wherein R′ has formula [I] or [II], and X is selected from NR 2 and OR, wherein each R is independently a linear or branched alkyl group having about 1 to about 10 carbon atoms which is optionally substituted with one or more halogen atoms, the method comprising reacting a compound containing an R′ group with a compound having formula SnX 4 ;
[I] CRaRbRc, wherein Ra is an aromatic ring having about 3 to about 10 carbon atoms which is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms, Rb and Rc are each independently hydrogen or a hydrocarbyl substituent having about 1 to about 10 carbon atoms, wherein each hydrocarbyl substituent is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms;
[II] CR A R B R C , wherein R A is (CH 2 ) n OR E , n is 0, 1, or 2, R E is a saturated hydrocarbon group having 1 to about 10 carbon atoms, R B and R C are each independently hydrogen or a saturated hydrocarbon group having about 1 to about 10 carbon atoms, wherein R′ contains about 2 to about 20 carbon atoms, wherein R A and one of R B and R C optionally form a 3 to 8-membered ring containing an ether linkage.

10 . A method of synthesizing a monoorgano tin compound having formula (1) having a purity of at least about 95 mol % and containing less than about 5 mol % of a diorgano tin compound having formula (2):
R′SnX 3   (1)
R′ 2 SnX 2   (2)
wherein R′ has formula [I] or [II], and X is selected from NR 2 and OR, wherein each R is independently a linear or branched alkyl group having about 1 to about 10 carbon atoms which is optionally substituted with one or more halogen atoms, the method comprising reacting a compound containing an OR or NR 2 group with a compound having formula R′SnY 3 , where Y is a reactive ligand;
[I] CRaRbRc, wherein Ra is an aromatic ring having about 3 to about 10 carbon atoms which is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms, Rb and Rc are each independently hydrogen or a hydrocarbyl substituent having about 1 to about 10 carbon atoms, wherein each hydrocarbyl substituent is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms;
[II] CRAR B R C , wherein R A is (CH 2 ) n OR E , n is 0, 1, or 2, R E is a saturated hydrocarbon group having 1 to about 10 carbon atoms, R B and R C are each independently hydrogen or a saturated hydrocarbon group having about I to about 10 carbon atoms, wherein R′ contains about 2 to about 20 carbon atoms, wherein R A and one of R B and R C optionally form a 3 to 8-membered ring containing an ether linkage.

11 . A method of synthesizing a monoorgano tin compound having formula (1) having a purity of at least about 95 mol % and containing less than about 5 mol % of a diorgano tin compound having formula (2):
R′SnX 3   (1)
R′ 2 SnX 2   (2)
wherein R′ has formula [I] or [II], and X is selected from NR 2 and OR, wherein each R is independently a linear or branched alkyl group having about 1 to about 10 carbon atoms which is optionally substituted with one or more halogen atoms, the method comprising reacting a compound containing an OR or NR 2 group with a compound having formula R′SnY 3 , where Y is a reactive ligand, the method comprising: (a) reacting a metal compound comprising an alkali metal M and a ligand X with a compound having formula SnY 2 to form a compound having formula MSnX 3 ; and (b) reacting the compound having formula MSnX 3 with a compound R′Z, wherein Z is a halogen atom and Y is a reactive ligand;
[I] CRaRbRc, wherein Ra is an aromatic ring having about 3 to about 10 carbon atoms which is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms, Rb and Rc are each independently hydrogen or a hydrocarbyl substituent having about 1 to about 10 carbon atoms, wherein each hydrocarbyl substituent is optionally substituted with one or more oxygen, nitrogen, and/or halogen atoms;
[II] CR A R B R C , wherein R A is (CH 2 ) n OR E , n is 0, 1, or 2, R E is a saturated hydrocarbon group having 1 to about 10 carbon atoms, R B and R C are each independently hydrogen or a saturated hydrocarbon group having about 1 to about 10 carbon atoms, wherein R′ contains about 2 to about 20 carbon atoms, wherein R A and one of R B and R C optionally form a 3 to 8-membered ring containing an ether linkage.

12 . A monoorgano tin compound having formula (1′) having a purity of at least about 95 mol % and containing less than about 5 mol % of a diorgano tin compound having formula (2′) and le

Assignees

• Gelest Inc
• Mitsubishi Chem Corp

Inventors

• Yang Li
• Caroff Christopher Michael
• Hioki Yuta
• Kiya Noriaki
• Ishii Koki

Classifications

• G03F7/0042

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

• C07F7/2296

  Purification, stabilisation, isolation · CPC title

• C07F7/2208

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C07F7/2224

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

• C07F7/2284 Primary

  Compounds with one or more Sn-N linkages · CPC title