Granted Patent B2

US 12,250,872 · App. 17/001,052 · Granted Mar 11, 2025

Inventors: Jui-Yi Tsai (Newtown, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Jerald Feldman (Cherry Hill, NJ); Zhiqiang Ji (Chalfont, PA); Hsiao-Fan Chen (Lawrence Township, NJ); Tyler Fleetham (Newtown, PA); Sean Michael Ryno (Yardley, PA); Rasha Hamze (Philadelphia, PA); Morgan C. Macinnis (Yardley, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/346H10K85/322H10K85/371H10K85/654H10K85/6572H10K85/6574H10K85/6576

Abstract

Claims (76)

1. A compound comprising a ligand L A of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N;

one of Y 1 or Y 2 is selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

the other of Y 1 or Y 2 is selected from the group consisting of Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

Z 1 and Z 2 are each independently C or N;

R A , R B , and R C each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;

each of R, R′, R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

the ligand L A is complexed to a metal M through the indicated dashed lines to form a 6-membered chelate ring;

M is selected from the group consisting of Pd, Pt, Cu, and Au;

any two substituents can be joined to form a ring; and

at least one of the following is true:

at least one of Y 1 or Y 2 is SiRR′ and GeRR′:

at least one of Y 1 or Y 2 comprises a substituent and said substituent joins with one of R A or R B to form a ring;

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein a linking atom separates ring A and ring B from the two other ligands; or

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein at least one of the two other ligands is substituted with terphenyl or a phenyl comprising two alkyl groups.

2. The compound of claim 1 , wherein each of R, R′, R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

3. The compound of claim 1 , wherein ring A and ring B are each 6-membered aromatic rings.

4. The compound of claim 1 , wherein one of Y 1 and Y 2 O and the other of Y 1 and Y 2 is NR, wherein R is a six-membered aryl or heteroaryl.

5. The compound of claim 1 , wherein X 1 -X 5 are each independently C.

6. The compound of claim 1 , wherein Z 1 and Z 2 are each independently C.

7. The compound of claim 1 , wherein the two other ligands are each independently selected from the group consisting of pyrazole, imidazole, isoimidazole, triazole, N-heterocyclic carbene, pyridine, pyrimidine, triazine, pyrazine, and pyridazine.

8. The compound of claim 1 , wherein M is Pt.

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

wherein X 6 -X 11 are each independently C or N and the rest are previously defined.

10. The compound of claim 1 , wherein the ligand L A can comprise a structure selected from the group consisting of ligands Ln-Yi-Yj, Ln′-Yi, and L137 to L142, wherein n is an integer from 1 to 100, n′ is an integer from 101 to 136, and i and j are each independently an integer from 1 to 30, wherein Ln-Yi-Yj have the following structures:

wherein Ln′-Yi have the following structures:

and

wherein L137 to L142 have the following structures:

wherein Y1 to Y30 have the following structures

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

12. An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a ligand L A of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N;

one of Y 1 or Y 2 is selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

the other of Y 1 or Y 2 is selected from the group consisting of Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

Z 1 and Z 2 are each independently C or N;

R A , R B , and R C each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;

each of R, R′, R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

the ligand L A is complexed to a metal M through the indicated dashed lines to form a 6-membered chelate ring;

M is selected from the group consisting of Pd, Pt, Cu, and Au;

any two substituents can be joined to form a ring; and

at least one of the following is true:

at least one of Y 1 or Y 2 is SiRR′ and GeRR′:

at least one of Y 1 or Y 2 comprises a substituent and said substituent joins with one of R A or R B to form a ring:

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein a linking atom separates ring A and ring B from the two other ligands; or

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein at least one of the two other ligands is substituted with terphenyl or a phenyl comprising two alkyl groups.

13. The OLED of claim 12 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

14. The OLED of claim 13 , wherein the host is selected from the group consisting of:

and combinations thereof.

15. A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a ligand L A of Formula I

wherein:

ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

X 1 -X 5 are each independently C or N;

one of Y 1 or Y 2 is selected from the group consisting of O, S, Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

the other of Y 1 or Y 2 is selected from the group consisting of Se, BR, NR, PR, CRR′, SiRR′, and GeRR′;

Z 1 and Z 2 are each independently C or N;

R A , R B , and R C each independently represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;

each of R, R′, R A , R B , and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

the ligand L A is complexed to a metal M through the indicated dashed lines to form a 6-membered chelate ring;

M is selected from the group consisting of Pd, Pt, Cu, and Au;

any two substituents can be joined to form a ring; and

at least one of the following is true:

at least one of Y 1 or Y 2 is SiRR′ and GeRR′;

at least one of Y 1 or Y 2 comprises a substituent and said substituent joins with one of R A or R B to form a ring;

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein a linking atom separates ring A and ring B from the two other ligands; or

the ligand L A is joined with two other ligands at ring A and ring B to form a tetradentate ligand, wherein at least one of the two other ligands is substituted with terphenyl or a phenyl comprising two alkyl groups.

16. A formulation comprising a compound according to claim 1 .

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

Assignments (2)

Continuity (4)

References Cited (195)