High purity tin compounds containing unsaturated substituent and method for preparation thereof

Patent metadata

Field	Value
Publication number	US-2025257082-A1
Application number	US-202519192884-A
Country	US
Kind code	A1
Filing date	Apr 29, 2025
Priority date	Aug 12, 2022
Publication date	Aug 14, 2025
Grant date	—

Abstract

Monoorgano tin trialkoxide compounds having chemical formula R′Sn(OR)3 and containing less than about 5 mol % diorgano tin dialkoxide are described. R′ is a linear or branched, optionally fluorinated, unsaturated hydrocarbon group having about 2 to about 20 carbon atoms and each R is independently a linear or branched, optionally fluorinated, 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

1 - 41 . (canceled)

42 . A composition comprising an organotin compound having formula (3) and an organotin compound having formula (4):
R′SnO (3/2−x/2) (OH) x   (3)
R″SnO (3/2−x/2) (OH) x   (4)
wherein 0<x<3, R′ is a linear or branched, fluorinated or unfluorinated, unsaturated hydrocarbon group having about 2 to about 20 carbon atoms, and R″ is an optionally substituted hydrocarbon group having about 2 to about 20 carbon atoms.

43 . The composition according to claim 42 , wherein at least one of the compound having formula (3) and the compound having formula (4) is obtained by hydrolysis of a monoorgano tin trialkoxide compound having formula (1):
R′Sn(OR) 3   (1)
wherein each R is independently a linear or branched, fluorinated or unfluorinated, alkyl group having about 1 to about 10 carbon atoms.

44 . A solution comprising the composition according to claim 42 and an organic solvent.

45 . The solution according to claim 44 , wherein at least one of the compound having formula (3) and the compound having formula (4) is obtained by hydrolysis of a monoorgano tin trialkoxide compound having formula (1):
R′Sn(OR) 3   (1)
wherein each R is independently a linear or branched, fluorinated or unfluorinated, alkyl group having about 1 to about 10 carbon atoms.

46 . A film comprising the composition according to claim 42 .

47 . The film according to claim 46 , wherein at least one of the compound having formula (3) and the compound having formula (4) is obtained by hydrolysis of a monoorgano tin trialkoxide compound having formula (1):
R′Sn(OR) 3   (1)
wherein each R is independently a linear or branched, fluorinated or unfluorinated, alkyl group having about 1 to about 10 carbon atoms.

48 . The composition according to claim 42 , wherein R′ is a linear or branched, fluorinated or unfluorinated, unsaturated hydrocarbon group having about 2 to about 10 carbon atoms.

49 . The composition according to claim 42 , wherein R′ is a fluorinated or unfluorinated vinyl (ethenyl), allyl, 1-propenyl, 3-buten-1-yl, 2-methyl allyl, 3-buten-2-yl, or 3-methyl-2-buten-1-yl group.

50 . The composition according to claim 42 , wherein R′ is a fluorinated or unfluorinated 3-buten-1-yl group.

51 . The composition according to claim 42 , wherein R′ is a linear or branched, fluorinated or unfluorinated, unsaturated hydrocarbon group having about 2 to about 20 carbon atoms, and R″ is an isopropyl group.

52 . The composition according to claim 42 , wherein R′ is a linear or branched, fluorinated or unfluorinated, unsaturated hydrocarbon group having about 2 to about 10 carbon atoms, and R″ is an isopropyl group.

53 . The composition according to claim 42 , wherein R′ is a fluorinated or unfluorinated vinyl (ethenyl), allyl, 1-propenyl, 3-buten-1-yl, 2-methyl allyl, 3-buten-2-yl, or 3-methyl-2-buten-1-yl group, and R″ is an isopropyl group.

54 . The composition according to claim 42 , wherein R′ is a fluorinated or unfluorinated 3-buten-1-yl group, and R″ is an isopropyl group.

55 . The composition according to claim 42 , wherein a weight ratio of the organotin compound having formula (3) to the organotin compound having formula (4) is about 90:10 to 10:90.

56 . The composition according to claim 42 , wherein a weight ratio of the organotin compound having formula (3) to the organotin compound having formula (4) is about 70:30 to 30:70.

Assignees

• Gelest Inc
• Mitsubishi Chem Corp

Inventors

• Yang Li
• Caroff Christopher Michael
• Hioki Yuta

Classifications

• C09D7/63

  organic · 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

• C07F7/2224 Primary

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