Metal complexes with boron-nitrogen heterocycle containing ligands

1. A compound comprising a monoanionic bidentate ligand L having the structure:

wherein A is pyridine;

wherein X 1 is nitrogen;

wherein X 2 , X 4 and X 6 are selected from the group consisting of carbon, nitrogen and boron,

wherein X 3 is nitrogen or boron;

wherein, when X 3 is boron, one of X 2 , X 4 and X 6 is nitrogen and the other two of X 2 , X 4 and X 6 are each carbon;

wherein, when X 3 is nitrogen, one of X 2 , X 4 and X 6 is boron and the other two of X 2 , X 4 and X 6 are each carbon;

wherein X 5 and X 7 are carbon;

wherein R 1 and R 2 represent mono, di, tri, or tetra substitutions;

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl; and

wherein X 1 and X 2 are coordinated to iridium.

2. The compound of claim 1 , wherein the ligand L is selected from the group consisting of:

wherein R 3 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl.

3. The compound of claim 1 , wherein the compound has the formula M n (L) a (L′) b (L″) c :

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and

wherein L′ and L″ are independently selected from the group consisting of:

wherein R′, R″, and R′″ are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl;

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

4. The compound of claim 1 , wherein the compound has the formula M n (L) a (L′) b (L″) c :

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and wherein L′ and L″ are independently selected from the group consisting of:

wherein R′, R″, and R′″ are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl;

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

5. The compound of claim 1 , wherein the compound is selected from the group consisting of:

wherein R 3 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl;

wherein R′, R″, and R′″ are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl;

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

6. The compound of claim 5 , wherein the compound is selected from the group consisting of:

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

7. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a monoanionic bidentate ligand L having the structure:

wherein A is pyridine;

wherein X 1 is nitrogen;

wherein X 2 , X 4 and X 6 are selected from the group consisting of carbon, nitrogen and boron,

wherein X 3 is nitrogen or boron;

wherein, when X 3 is boron, one of X 2 , X 4 and X 6 is nitrogen and the other two of X 2 , X 4 and X 6 are each carbon;

wherein, when X 3 is nitrogen, one of X 2 , X 4 and X 6 is boron and the other two of X 2 , X 4 and X 6 are each carbon;

wherein X 5 and X 7 are carbon;

wherein R 1 and R 2 represent mono, di, tri, or tetra substitutions;

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl; and

wherein X 1 and X 2 are coordinated to iridium.

8. The device of claim 7 , wherein the ligand L is selected from the group consisting of:

wherein R 3 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl.

9. The device of claim 7 , wherein the compound has the formula M n (L) a (L′) b (L″) c :

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and

wherein L′ and L″ are independently selected from the group consisting of:

wherein R′, R″, and R′″ is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl;

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

10. The device of claim 7 ,

wherein the compound is selected from the group consisting of:

wherein X is selected from the group consisting of S, NZ, O, Se, BZ, CZZ′, and C═O;

wherein R 3 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl;

wherein R′, R″, and R′″ are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aryl, and heteroaryl; and

wherein Z and Z′ are independently selected from the group consisting of hydrogen, alkyl, and aryl.

11. The device of claim 7 , wherein the organic layer is an emissive layer and the compound comprising the ligand L having FORMULA II is an emitting dopant; and the organic layer further comprises a host containing a benzene, carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, naphthalene, triphenylene, or biphenyl moiety.

12. A consumer product comprising a device, the device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a monoanionic bidentate ligand L having the formula:

wherein A is pyridine;

wherein X 1 is nitrogen;

wherein X 2 , X 4 and X 6 are selected from the group consisting of carbon, nitrogen and boron,

wherein X 3 is nitrogen or boron;

wherein, when X 3 is boron, one of X 2 , X 4 and X 6 is nitrogen and the other two of X 2 , X 4 and X 6 are each carbon;

wherein, when X 3 is nitrogen, one of X 2 , X 4 and X 6 is boron and the other two of X 2 , X 4 and X 6 are each carbon;

wherein X 5 and X 7 are carbon;

wherein R 1 and R 2 represent mono, di, tri, or tetra substitutions;

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, aryl, and heteroaryl; and

wherein X 1 and X 2 are coordinated to iridium.