Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9722193-B2
Application number	US-201615365360-A
Country	US
Kind code	B2
Filing date	Nov 30, 2016
Priority date	Feb 10, 2006
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

Compounds comprising phosphorescent metal complexes comprising cyclometallated imidazo[1,2-f]phenanthridine and diimidazo[1,2-a:1′,2′-c]quinazoline ligands, or isoelectronic or benzannulated analogs thereof, are described. Organic light emitting diode devices comprising these compounds are also described.

First claim

We claim:

1. A phosphorescent compound comprising a metal and a monoanionic, bidentate ligand selected from the group below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein:
E 1a-q are each, independently, selected from the group consisting of C and N, and collectively comprise an 18 pi-electron system; provided that E 1a and E 1p are different; and
R 1a-h are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; provided that R 1a-i is other than H when attached to N.

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

wherein R 1a-h are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1a-i and R 2a-c may be linked to form a ring.

3. An organic light emitting device comprising the phosphorescent compound of claim 1 .

4. A consumer product comprising an organic light-emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a phosphorescent compound comprising a metal and a monoanionic, bidentate ligand selected from the group below, wherein the metal is selected from the group consisting of the non-radioactive metals with atomic numbers greater than 40, and wherein the bidentate ligand may be linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand;

wherein:
E 1a-q are each, independently, selected from the group consisting of C and N, and collectively comprise an 18 pi-electron system; provided that E 1a and E 1p are different; and
R 1a-h are each, independently, H, hydrocarbyl, heteroatom substituted hydrocarbyl, cyano, fluoro, OR 2a , SR 2a , NR 2a R 2b , BR 2a R 2b , or SiR 2a R 2b R 2c , where R 2a-c are each, independently, hydrocarbyl or heteroatom substituted hydrocarbyl, and where any two of R 1a-i and R 2a-c may be linked to form a saturated or unsaturated, aromatic or non-aromatic ring; provided that R 1a-i is other than H when attached to N.

5. The consumer product of claim 4 , wherein the consumer product is selected from the group consisting of flat panel displays, computer monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, personal digital assistants (PDAs), laptop computers, digital cameras, camcorders, viewfinders, micro-displays, vehicles, a wall, theater or stadium screen, and a sign.

Assignees

• Universal Display Corp

Inventors

• Knowles David
• Lin Chun
• Mackenzie Peter
• Tsai Jui-Yi
• Walters Robert W
• Beers Scott
• Brown Cory S
• Yeager Walter

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1081

  with sulfur · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1066

  with sulfur · CPC title

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title