Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10930864-B2
Application number	US-201815952817-A
Country	US
Kind code	B2
Filing date	Apr 13, 2018
Priority date	May 10, 2017
Publication date	Feb 23, 2021
Grant date	Feb 23, 2021

Abstract

The present invention includes novel metal complexes of 5H-benzimidazo[1,2-a]benzimidazole (“BimBim”) and related ligands. The novel ligands may coordinate to one or two metal centers. The metal complexes of the present invention comprising these ligands may be useful as emissive materials and n-dopants in OLED devices.

First claim

We claim:

1. A compound having a formula selected from the group consisting of:

wherein M 1 and M 2 are metal atoms;
wherein X 1 -X 8 are each independently selected from group consisting of carbon and nitrogen;
wherein Y is N, O, or S;
wherein the dashed line (----) represents no bond to the maximum possible number of allowed bonds;
wherein L 1 and L 2 are one or more ligands that are optionally attached to M 1 and M 2 , respectively;
wherein when L 1 or L 2 are present, m or n has a value of at least one and is the maximum number of ligands L 1 and L 2 that may be attached to M 1 and M 2 , respectively;
wherein L 1 and L 2 may be joined together to form a bridging ligand;
wherein R 1 and R 2 each independently represent mono to the maximum possible number of substitutions, or no substitution;
wherein each R 1 and R 2 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two adjacent R 1 or R 2 are optionally joined or fused to form a ring; and
wherein p is an integer between 1 and 4.

2. The compound of claim 1 , wherein each R 1 and R 2 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, and combinations thereof.

3. The compound of claim 1 , wherein M 1 and M 2 are each independently selected from the group consisting of Cr, Mo, W, Os, Ir, Pd, and Pt.

4. The compound of claim 1 , wherein M′ is the same as M 2 .

5. The compound of claim 1 , wherein M′ is different from M 2 .

6. The compound of claim 1 , wherein X 1 -X 8 are carbon.

7. The compound of claim 1 , wherein at least one of X 1 -X 8 is nitrogen.

8. The compound of claim 1 , wherein Y is N.

9. The compound of claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of:

wherein each Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f RR, SiR e R f , and GeR e R f ;
wherein R e and R f are optionally fused or joined to form a ring;
wherein each R a , R b , R e , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each R a , R b , R e , R d , R e and R f is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.

10. The compound of claim 9 , wherein L 1 and L 2 are each independently selected from the group consisting of:

11. The compound of claim 9 , wherein L 1 and L 2 are each independently selected from the group consisting of:

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Silverstein Daniel W
• Brooks Jason
• Feldman Jerald

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• H01L51/0084

  Electricity · mapped topic