IP Library › Granted Patent US 8,871,304
Granted Patent B2
US 8,871,304 · App. 13/882,824 · Granted Oct 28, 2014

(Amide amino alkane) metal compound, method of manufacturing metal-containing thin film using said metal compound

Inventors: Osamu Fujimura (Ube, JP); Hiroki Kanato (Ichihara, JP); Masashi Shirai (Ube, JP); Hiroshi Nihei (Ube, JP)
Assignee: Ube Industries, Ltd.
H01L51/0083H01L51/0084H01L51/0077H01L51/0089H01L51/0092C07F15/065C07F15/045C07F5/003C07F15/025C07F13/005C07F3/02C07F3/06
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Quick Facts
Patent No.
US 8,871,304
App. No.
13/882,824
Granted
Oct 28, 2014
Kind
B2
Abstract

The present invention relates to an (amide amino alkane) metal compound represented by the formula (1): wherein M represents a metal atom; R 1 represents a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms; R 2 and R 3 may be the same as, or different from each other, and each independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, or R 2 and R 3 may form a substituted or unsubstituted 5- or 6-membered ring together with the nitrogen atom to which they are bound; Z represents a linear or branched alkylene group having 1 to 10 carbon atoms (a part of which may optionally form a ring); and n represents a number of the ligands, which is equal to the valence of the metal (M), and represents an integer of from 1 to 3; with the proviso that the metal compounds in which M is Li (Lithium), Be (Beryllium), Ge (Germanium) or Nd (Neodymium) are excluded; the metal compounds in which M is Mg (Magnesium) and R 1 is methyl group are excluded; the metal compounds in which M is Zn (Zinc) and R 1 is methyl group are excluded; the metal compounds in which M is Bi (Bismuth) and R 1 is t-butyl group are excluded; and in cases where n is two or greater, two or more ligands may be the same as, or different from each other; and a method of producing a metal-containing thin film using the metal compound.

Claims (58)

1. An (amide amino alkane) metal compound represented by the formula (1);

wherein

M represents a metal atom;

R 1 represents a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms;

R 2 and R 3 may be the same as, or different from each other, and each independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, or R 2 and R 3 may form a substituted or unsubstituted 5- or 6-membered ring together with the nitrogen atom to which they are bound;

Z represents a linear or branched alkylene group having 1 to 10 carbon atoms (a part of which may optionally form a ring); and

n represents a number of the ligands, which is equal to the valence of the metal (M), and represents an integer of from 1 to 3;

with the proviso that

the metal compounds in which M is Li (Lithium), Be (Beryllium), Ge (Germanium) or Nd (Neodymium) are excluded;

the metal compounds in which M is Mg (Magnesium) and R 1 is methyl group are excluded;

the metal compounds in which M is Zn (Zinc) and R 1 is methyl group are excluded;

the metal compounds in which M is Bi (Bismuth) and R 1 is t-butyl group are excluded; and

in cases where n is two or greater, two or more ligands may be the same as, or different from each other.

2. The (amide amino alkane) metal compound as claimed in claim 1 , wherein M is sodium, magnesium, manganese, iron, cobalt, nickel, zinc, yttrium, lanthanum, or indium.

3. The (amide amino alkane) metal compound as claimed in claim 1 , wherein Z is a linear or branched alkylene group having 1 to 5 carbon atoms, or a group represented by the formula:

wherein

Z 1 represents a linear alkylene group having 1 to 3 carbon atoms, and

R represents a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms.

4. A method of producing an (amide amino alkane) metal compound as claimed in claim 1 , which is represented by the formula (1):

wherein M, R 1 , R 2 , R 3 , Z and n are defined as above;

comprising a step of;

reacting a mono- or di-alkyl metal compound represented by the formula (2a) or (2b):

R 4 M  (2a)

R 4 R 5 M  (2b)

wherein

M represents a metal atom; and

R 4 and R 5 may be the same as, or different from each other, and each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms;

with a di-amino alkane compound represented by the formula (3):

wherein R 1 , R 2 , R 3 and Z are defined as above.

5. A method of producing an (amide amino alkane) metal compound as claimed in claim 1 , which is represented by the formula (1);

wherein M, R 1 , R 2 , R 3 , Z and n are defined as above;

comprising steps of

reacting an alkyl alkali metal compound represented by the formula (4a);

R 4 A  (4a)

wherein

R 4 represents a linear or branched alkyl group having 1 to 10 carbon atoms; and

A represents an alkali metal atom;

or an alkali metal with a di-amino alkane compound represented by the formula (3):

wherein R 1 , R 2 , R 3 and Z are defined as above;

to form a (amide amino alkane) alkali metal compound represented by the formula (5):

wherein R 1 , R 2 , R 3 , A and Z are defined as above; and

reacting the (amide amino alkane) alkali metal compound with a metal halide compound represented by the formula (6):

MX n   (6)

wherein

M represents a metal atom;

X represents a halogen atom; and

n represents a number of the halogen atoms, which is equal to the valence of the metal (M), and represents an integer of from 1 to 3.

6. A method of producing an (amide amino alkane) metal compound as claimed in claim 1 , which is represented by the formula (1):

wherein R 1 , R 2 , R 3 , M, Z and n are defined as above;

comprising a step of:

reacting a metal represented by the formula (7):

M  (7)

wherein

M represents a metal atom, and is defined as above;

with a di-amino alkane compound represented by the formula (3):

wherein R 1 , R 2 , R 3 and Z are defined as above.

7. A method of producing a metal-containing thin film by a chemical vapor deposition method, wherein an (amide amino alkane) metal compound as claimed in claim 1 is used as a source.

8. A material for forming a metal-containing thin film, comprising an (amide amino alkane) metal compound as claimed in claim 1 .

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE INVENTORS ARE OMITTED PREVIOUSLY RECORDED ON REEL 030328 FRAME 0473. ASSIGNOR(S) HEREBY CONFIRMS THE UBE INDUSTRIES, LTD.. Recorded Jul 23, 2013
From: FUJIMURA, OSAMU; KANATO, HIROKI; SHIRAI, MASASHI; NIHEI, HIROSHI
To: UBE INDUSTRIES, LTD.
Reel/Frame 030855/0895 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2013
From: FUJIMURA, OSAMU; KANATO, HIROKI
To: UBE INDUSTRIES, LTD.
Reel/Frame 030328/0473 →
Priority Claims (4)
JP 2010-245941 · Nov 2, 2010 · national
JP 2011-000372 · Jan 5, 2011 · national
JP 2011-170697 · Aug 4, 2011 · national
JP 2011-192228 · Sep 5, 2011 · national
Continuity (1)
Related Publication 20130273250A1 · Oct 17, 2013