IP Library Granted Patent US 9,643,988
Granted Patent B2
US 9,643,988 · App. 14/490,628 · Granted May 9, 2017

Compounds having low ionization energy

Inventors: Dennis Lichtenberger (Tucson, AZ); Carlos Murillo (College Station, TX)
Assignee: The Arizona Board of Regents on behalf of the University of Arizona
C07F11/00B01J31/2295C07D487/04C07F11/005B01J2231/005B01J2531/66
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Quick Facts
Patent No.
US 9,643,988
App. No.
14/490,628
Granted
May 9, 2017
Kind
B2
Abstract

The present invention provides compounds that are soluble in a non-polar solvent and having a low ionization energy and negative oxidation potentials in tetrahydrofuran (THF). The present invention also provides a method for producing and using the same.

Claims (36)

1. A thin film comprising a compound of the formula: M a (L) b X c , wherein each M is independently tungsten or chromium; each L is independently a bicyclic heterocyclic anionic compound; X is a halide; a is 1 or 2; b is an integer from 1 to 4; and c is an integer from 0 to 2, and wherein said solid crystal has an onset ionization energy of about 4 eV or less and is soluble in an organic solvent.

2. The thin film of claim 1 , wherein said compound is soluble in an aprotic organic solvent.

3. The thin film of claim 1 , wherein said compound is soluble in a nonpolar organic solvent.

4. The thin film of claim 1 , wherein said compound has an oxidation potential in THF of about −1.5 V or less.

5. The thin film of claim 4 , wherein said compound has an oxidation potential in THF of about −1.8 V or less.

6. The thin film of claim 1 , wherein said compound has an onset ionization energy of about 3.6 eV or less.

7. The substrate of claim 1 , wherein the solubility of said compound in THF is at least 0.1 g/L.

8. The thin film of claim 7 , wherein the solubility of said compound in THF is at least 1 g/L.

9. The thin film of claim 1 , wherein the solubility of said compound in benzene is at least 0.1 g/L.

10. The thin film of claim 7 , wherein the solubility of said compound in benzene is at least 1 g/L.

11. An integrated circuit comprising a compound of the formula: M a (L) b X c , wherein each M is independently tungsten or chromium; each L is independently a bicyclic heterocyclic anionic compound; X is a halide; a is 1 or 2; b is an integer from 1 to 4; and c is an integer from 0 to 2, and wherein said compound has an oxidation potential in THF of about −1.5 V or less, and is soluble in an organic solvent.

12. The integrated circuit of claim 11 , wherein said compound has an oxidation potential in THF of about −1.8 V or less.

13. The integrated circuit of claim 11 , wherein said compound has an onset ionization energy of about 4 eV or less.

14. The integrated circuit of claim 13 , wherein said compound has an onset ionization energy of about 3.6 eV or less.

15. A compound of the formula:

M a (L) b X c

wherein

each M is independently tungsten or chromium;

each L is independently a bicyclic heterocyclic anionic compound;

X is a halide;

a is 1 or 2;

b is an integer from 1 to 4; and

c is an integer from 0 to 2.

16. The compound of claim 15 , wherein said bicyclic heterocyclic anionic compound is of the formula:

wherein

each of m and n is independently an integer from 0 to 4, provided the sum of m and n is at least 1; and

each of R 1 and R 2 is independently alkyl.

17. The compound of claim 16 , wherein R 1 and R 2 are independently methyl, or ethyl.

18. The compound of claim 16 , wherein m is 2.

19. The compound of claim 16 , wherein n is 2.

20. The compound of claim 16 , wherein said compound is of the formula:

M 2 (L) 4 X c

wherein

M and X are those defined in claim 15 ;

L is that defined in claim 16 ; and

c is an integer of 0 or 2.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2016
From: LICHTENBERGER, DENNIS; MURILLO, CARLOS
To: THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA
Reel/Frame 039181/0895 →
CONFIRMATORY LICENSE Recorded Apr 9, 2015
From: UNIVERSITY OF ARIZONA
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 035389/0584 →
Continuity (2)
Provisional Application 61880135 · Sep 19, 2013
Related Publication 20150080571A1 · Mar 19, 2015