IP Library › Granted Patent US 8,058,798
Granted Patent B2
US 8,058,798 · App. 12/580,844 · Granted Nov 15, 2011

Emissive metal complexes

Assignee: Massachusetts Institute of Technology
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Quick Facts
Patent No.
US 8,058,798
App. No.
12/580,844
Granted
Nov 15, 2011
Kind
B2
Abstract

Monomeric metal complexes having desirable luminescence properties are provided. In one embodiment, a monomeric metal compound is represented by the formula (ArN)M(L) x , where ArN is an arylamido ligand, and M may be any metal capable of exhibiting luminescent properties, for example, a d 10 metal. L may be a tertiary phosphine.

Claims (88)

1. A compound represented by Formula II:

wherein:

L is Z(R c ) 3 or has the formula:

Z is P, and Z′, if present, is P;

R d is a group selected from an optionally substituted alkylene group optionally interrupted by O, S or NR b , an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted arylalkylene group, and an optionally substituted heteroarylalkylene group;

x is 1 or 2;

each of R 1 through R 10 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

2. The compound of claim 1 , wherein the compound is (Ph 3 P) 2 Cu(NPh 2 ), (Ph 3 P) 2 Cu(NTol 2 ), or (Ph 3 P) 2 Cu(N(ρ-FPh) 2 ).

3. A monomeric metal compound represented by Formula I:

wherein:

L has the formula

x is 1; and

Z and Z′ are each independently P;

each R c , independently, is a group selected from hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;

R d is a group selected from an optionally substituted alkylene group optionally interrupted by O, S or NR b , an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted arylalkylene group, and an optionally substituted heteroarylalkylene group;

M is Cu, Ag, Au, Zn, Cd or Hg; and

R a is an optionally substituted aryl group;

R b is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; or

R a and R b and N together form an aryl group.

4. The compound of claim 3 , wherein the compound is represented by Formula III:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 5 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;

R 11 is selected from the group consisting of hydrogen, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

5. The compound of claim 3 , wherein the compound is represented by Formula IV:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 8 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

6. The compound of claim 3 , wherein the compound is represented by Formula V:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 6 independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

7. The compound of claim 3 , wherein L is a bisphosphinoalkane family ligand, a BISBI family ligand, a DPPF family ligand, a XANTphos family ligand, or a BINAP family ligand.

8. A luminescent device including a compound represented by Formula II:

wherein:

L is Z(R c ) 3 or has the formula:

Z is P, and Z′, if present, is P;

R d is a group selected from an optionally substituted alkylene group optionally interrupted by O, S or NR b , an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted arylalkylene group, and an optionally substituted heteroarylalkylene group;

x is 1 or 2;

each of R 1 through R 10 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

9. The device of claim 8 , wherein the compound is (Ph 3 P) 2 Cu(NPh 2 ), (Ph 3 P) 2 Cu(NTol 2 ), or (Ph 3 P) 2 Cu(N(ρ-FPh) 2 ).

10. A luminescent device including a compound represented by Formula I:

wherein:

L has the formula

x is 1; and

Z and Z′ are each independently P;

each R c , independently, is a group selected from hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;

R d is a group selected from an optionally substituted alkylene group optionally interrupted by O, S or NR b , an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted arylalkylene group, and an optionally substituted heteroarylalkylene group;

M is Cu, Ag, Au, Zn, Cd or Hg; and

R a is an optionally substituted aryl group;

R b is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; or

R a and R b and N together form an aryl group.

11. The device of claim 10 , wherein the compound is represented by Formula III:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 5 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;

R 11 is selected from the group consisting of hydrogen, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

12. The device of claim 10 , wherein the compound is represented by Formula IV:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 8 , independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

13. The device of claim 10 , wherein the compound is represented by Formula V:

wherein:

Z is P, and Z′ is P;

each of R 1 through R 6 independently, is selected from the group consisting of hydrogen, a halogen, hydroxyl, cyano, nitro, di(alkyl)amino, an alkoxy group, an acyl group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group; and

each R c , independently, is selected from the group consisting of hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group.

14. The device of claim 10 , wherein L is a bisphosphinoalkane family ligand, a BISBI family ligand, a DPPF family ligand, a XANTphos family ligand, or a BINAP family ligand.

15. The device of claim 10 , further comprising an electric power source configured to electrically excite the compound.

16. A method of generating light comprising:

exciting a compound represented by Formula I

wherein:

L has the formula:

Z and Z′ are each independently P;

each R c , independently, is a group selected from hydrogen, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group;

R d is a group selected from an optionally substituted alkylene group, an optionally substituted arylene group, an optionally substituted heteroarylene group, an optionally substituted arylalkylene group, and an optionally substituted heteroarylalkylene group;

x is 1;

M is Cu, Ag, Au, Zn, Cd or Hg; and

R a is an optionally substituted aryl group;

R b is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group; or

R a and R b and N together form an aryl group.

17. The method of claim 16 , wherein exciting the compound includes photoexcitation or electrical excitation.

Assignments (2)
CONFIRMATORY LICENSE Recorded May 24, 2012
From: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 028274/0744 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 8, 2009
From: PETERS, JONAS C.; LOTITO, KENNETH J.
To: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
Reel/Frame 023622/0544 →
Continuity (1)
Related Publication 20110089818A1 · Apr 21, 2011