Tridentate cyclometalated metal complexes with six-membered coordination rings

1. A complex represented by Formula 3:

wherein:

M is Pt(II), Pd(II), Ir(I), Rh(I), or Au(II),

x is 1;

y is 1;

z is 1;

each n is independently an integer of 1 to 4, valency permitting,

each R 1 , R 2 , and R 3 is independently hydrogen, halogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted alkyl, alkoxyl, alkenyl, alkynyl, heteroaryl, or aryl; and any two of R 1 , any two of R 2 , and any two of R 3 are optionally linked together;

Y 1a is N;

Y 1b is N;

Y 3b is N;

Y 3a is C:

Y 3c , Y 3d , and Y 3e are C or N;

Y 2c is N;

Y 2d , Y 4c , and Y 4d are C or N;

Y 2b , Y 4b , and Y 2a are C;

Y 4a is C or N;

Ar 1 , Ar 2 , and Ar 3 are aromatic;

Y is halogen, OCOR 7a , OR 7b , SR 7c , NR 7d R 7e , CO, NR 7f , PR 7g , AsR 7h R 7i R 7j , C≡CR 7k , substituted or unsubstituted: pyridine, imidazole, pyrazole, oxazole, thiazole, isoxazole, or quinoline, where each of R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g , R 7h , R 7i , R 7j , and R 7k is independently acetylacetonate, pyridine, imidazole or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or trisubstituted phosphine;

p is 4:

each R 4 and R 5 is independently hydrogen, halogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted alkyl, alkoxyl, alkenyl, alkynyl, heteroaryl, or aryl;

any two of R 4 are optionally linked together; and

any two of R 5 are optionally linked together.

2. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:

U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR;

M is Pt(II) or Pd(II);

each R is independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl; and

each Ar 1 is independently selected from the group consisting of 6-membered substituted or unsubstituted heteroaryl.

3. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:

U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR;

M is Rh(I) or Ir(I);

each R is independently selected from the group consisting of hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl; and

each Ar 1 is 6-membered substituted or unsubstituted heteroaryl.

4. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:

U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR;

M is Au(III);

each R is independently hydrogen, halogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl;

n is an integer of 1 to 4; and

each Ar 1 is independently 6-membered substituted or unsubstituted heteroaryl.

5. A light emitting device comprising the complex of claim 1 .

6. An OLED device comprising the complex of claim 1 .

7. The OLED device of claim 6 , wherein the device is a phosphorescent OLED device.

8. A photovoltaic device comprising the complex of claim 1 .

9. A luminescent display device comprising the complex of claim 1 .

10. The complex of claim 1 , wherein the complex has the structure:

11. The complex of claim 1 , wherein M is Pt(II).

12. The complex of claim 1 , wherein R 1 , R 2 , and R 3 are each independently hydrogen, halogen, hydroxyl, amino, or substituted or unsubstituted alkyl.

13. The complex of claim 1 , wherein R 1 , R 2 , and R 3 are hydrogen.

14. The complex of claim 1 , wherein Y is halogen, OCOR 7a , OR 7b , SR 7c , NR 7d R 7e , CO, NR 7f , PR 7g , AsR 7h R 7i R 7j , or C≡CR 7k .

15. The complex of claim 1 , wherein Y is halogen.

16. The complex of claim 1 , wherein R 4 and R 5 are hydrogen.

17. The complex of claim 2 , wherein

M is Pd(II);

each R is independently hydrogen; and

each Ar 1 is independently 6-membered unsubstituted heteroaryl.