Organometallic compound, organic light emitting diode and organic light emitting device including the same

1. An organometallic compound of Formula 1:

wherein M is platinum (Pt) or palladium (Pd), and X1 is selected from the group consisting of oxygen (O), sulfur (S), and NR 6 ,

wherein X2 is NR 6 ,

wherein Y is selected from the group consisting of a single bond, *—O—*, *—S—*, *—Se—* *—CR7R8-*, *—CR7═CR8-*, *—NR9-*, *—C(═O)—*, *—S(═O)—*, *—S(═O) 2 —*, and *—SiR7R8-*,

wherein each of R1 to R9 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic, C3 to C20 heteroalicyclic, C6 to C30 aromatic, and C3 to C30 heteroaromatic, or adjacent two of R1 to R9 are combined with each other to form a fused ring,

R2′ and R5′ are combined with each other to form a fused ring, and

wherein each of n1, n2, and n5 is independently an integer of 0 to 2, and each of n3 and n4 is independently an integer of 0 to 4.

2. The organometallic compound according to claim 1 , wherein the Formula 1 is represented by Formula 2:

wherein X3 is NR10, O, S, or CR11R12, and

wherein each of R10 to R12 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 cycloaliphatic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic group, and C3 to C30 heteroaromatic group.

3. The organometallic compound according to claim 1 , wherein the Formula 1 is represented by one of Formulas 3-1 to 3-3:

wherein R13 is selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic, and C3 to C30 heteroaromatic group, and n6 is an integer of 0 to 4.

4. The organometallic compound according to claim 1 , wherein the Formula 1 is represented by one of Formulas 4-1 to 4-3:

wherein X3 is NR10, O, S or CR11R12, and each of R10 to R12 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic group, and C3 to C30 heteroaromatic group, and

wherein R13 is selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic, and C3 to C30 heteroaromatic group, and n6 is an integer of 0 to 4.

5. The organometallic compound according to claim 1 , wherein the organometallic compound is selected from:

6. An organic light emitting diode, comprising:

a first electrode;

a second electrode facing the first electrode; and

a first emitting unit positioned between the first and second electrodes and including a first emitting material layer,

wherein the first emitting material layer includes an organometallic compound of Formula 1:

wherein M is platinum (Pt) or palladium (Pd), and X1 is selected from the group consisting of oxygen (O), sulfur (S) and NR 6 ,

wherein X2 is NR 6 ,

wherein Y is selected from the group consisting of a single bond, *—O—*, *—S—*, *—Se—* *—CR7R8-*, *—CR7-CR8-*, *—NR9-*, *—C(═O)—*, *—S(═O)—*, *—S(═O) 2 —*, and *—SiR7R8-*,

wherein each of R1 to R9 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic, C3 to C20 heteroalicyclic, C6 to C30 aromatic, and C3 to C30 heteroaromatic, or adjacent two of R1 to R9 are combined with each other to form a fused ring,

R2′ and R5′ are combined with each other to form a fused ring, and

wherein each of n1, n2, and n5 is independently an integer of 0 to 2, and each of n3 and n4 is independently an integer of 0 to 4.

7. The organic light emitting diode according to claim 6 , wherein the first emitting material layer includes a first host and a first dopant, and the first dopant is the organometallic compound.

8. The organic light emitting diode according to claim 6 , further comprising:

a second emitting unit including a second emitting material layer and positioned between the first emitting unit and the first electrode; and

a first charge generation layer positioned between the first and second emitting units,

wherein the second emitting material layer includes a blue dopant.

9. The organic light emitting diode according to claim 8 , wherein the first emitting unit further includes a third emitting material layer on or under the first emitting material layer, and

wherein the third emitting material layer includes a red dopant.

10. The organic light emitting diode according to claim 8 , further comprising:

a third emitting unit positioned between the first emitting unit and the second electrode and including a third emitting material layer; and

a second charge generation layer positioned between the first and third emitting units,

wherein the third emitting material layer includes a green dopant.

11. The organic light emitting diode according to claim 8 , further comprising:

a third emitting unit positioned between the first emitting unit and the second electrode and including a third emitting material layer; and

a second charge generation layer positioned between the first and third emitting units,

wherein the first emitting unit further includes a fourth emitting material layer on or under the first emitting material layer, and

wherein the third emitting material layer includes a blue dopant, and the fourth emitting material layer includes a red dopant.

12. The organic light emitting diode according to claim 6 , wherein the Formula 1 is represented by Formula 2:

wherein X3 is NR10, O, S, or CR11R12, and

wherein each of R10 to R12 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 cycloaliphatic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic group, and C3 to C30 heteroaromatic group.

13. The organic light emitting diode according to claim 6 , wherein the organometallic compound is selected from:

14. An organic light emitting display device, comprising:

a substrate;

an organic light emitting diode disposed on or over the substrate, the organic light emitting diode including:

a first electrode;

a second electrode facing the first electrode;

a first emitting unit positioned between the first and second electrodes and including a first emitting material layer; and

a thin film transistor positioned between the substrate and the organic light emitting diode and connected to the organic light emitting diode,

wherein the first emitting material layer includes an organometallic compound of Formula 1:

wherein M is platinum (Pt) or palladium (Pd), and X1 is selected from the group consisting of oxygen (O), sulfur (S), and NR 6 ,

wherein X2 is NR 6 ,

wherein Y is selected from the group consisting of a single bond, *—O—*, *—S—*, *—Se—*, *—CR7R8-*, *—CR7=CR8-*, *—NR9-*, *—C(═O)—*, *—S(═O)—*, *—S(═O) 2 —*, and *—SiR7R8-*,

wherein each of R1 to R9 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic, C3 to C20 heteroalicyclic, C6 to C30 aromatic, and C3 to C30 heteroaromatic, or adjacent two of R1 to R9 are combined with each other to form a fused ring,

R2′ and R5′ are combined with each other to form a fused ring, and

wherein each of n1, n2, and n5 is independently an integer of 0 to 2, and each of n3 and n4 is independently an integer of 0 to 4.

15. The organic light emitting display device according to claim 14 , wherein the organic light emitting diode further includes:

a second emitting unit including a second emitting material layer and positioned between the first emitting unit and the first electrode; and

a first charge generation layer positioned between the first and second emitting units,

wherein the second emitting material layer includes a blue dopant.

16. The organic light emitting display device according to claim 15 , wherein the first emitting unit further includes a third emitting material layer on or under the first emitting material layer, and

wherein the third emitting material layer includes a red dopant.

17. The organic light emitting display device according to claim 15 , wherein the organic light emitting diode further includes:

a third emitting unit positioned between the first emitting unit and the second electrode and including a third emitting material layer; and

a second charge generation layer positioned between the first and third emitting units,

wherein the third emitting material layer includes a green dopant.

18. The organic light emitting display device according to claim 15 , wherein the organic light emitting diode further includes:

a third emitting unit positioned between the first emitting unit and the second electrode and including a third emitting material layer; and

a second charge generation layer positioned between the first and third emitting units,

wherein the first emitting unit further includes a fourth emitting material layer on or under the first emitting material layer, and

wherein the third emitting material layer includes a blue dopant, and the fourth emitting material layer includes a red dopant.

19. The organic light emitting display device according to claim 15 , wherein a red pixel, a green pixel and a blue pixel are defined on the substrate, and the organic light emitting diode corresponds to each of the red, green and blue pixels, and

wherein the organic light emitting device further includes:

a color filter layer disposed between the substrate and the organic light emitting diode or on the organic light emitting diode and corresponding to the red, green and blue pixels.

20. The organic light emitting display device according to claim 14 , wherein the Formula 1 is represented by Formula 2:

wherein X3 is NR10, O, S, or CR11R12, and

wherein each of R10 to R12 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 cycloaliphatic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic group, and C3 to C30 heteroaromatic group.

21. An organometallic compound is represented by Formula 4-3:

wherein M is platinum (Pt) or palladium (Pd),

wherein X1 is selected from the group consisting of oxygen (O), sulfur (S), and NR 6 , and X2 is NR 6 ,

wherein each of R1 to R6 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic, C3 to C20 heteroalicyclic, C6 to C30 aromatic, and C3 to C30 heteroaromatic, or adjacent two of R1 to R6 are combined with each other to form a fused ring,

wherein each of n1, n2, and n5 is independently an integer of 0 to 2, and each of n3 and n4 is independently an integer of 0 to 4,

wherein R13 is selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic, and C3 to C30 heteroaromatic group, and n6 is an integer of 0 to 4, and

wherein X3 is NR10, O, S or CR11R12, and each of R10 to R12 is independently selected from the group consisting of deuterium, halogen, hydroxy group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1 to C20 alkyl group, C2 to C20 alkenyl group, C2 to C20 alkynyl group, C1 to C20 alkoxy group, C3 to C20 alicyclic group, C3 to C20 heteroalicyclic group, C6 to C30 aromatic group, and C3 to C30 heteroaromatic group.

22. The organometallic compound according to claim 21 , wherein the organometallic compound is selected from: