Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2016240798-A1
Application number	US-201615010560-A
Country	US
Kind code	A1
Filing date	Jan 29, 2016
Priority date	Feb 10, 2006
Publication date	Aug 18, 2016
Grant date	—

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 as set forth 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 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-i 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, and

is excluded from the bidentate ligand.

2 . The compound of claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au, and the bidentate ligand is selected from the group consisting of:

wherein:
R 1a-i 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.

3 . The compound of claim 2 , wherein the bidentate ligand is of the formula gs1-1.

4 . The compound of claim 2 , wherein the metal is Ir or Pt.

5 . The compound of claim 1 , wherein the metal is selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, Pt, and Au, and at least one of R 1a-i is a 2,6-di-substituted aryl group.

6 . The compound of claim 5 , wherein R 1b is a 2,6-di-substituted aryl group.

7 . The compound of claim 6 , wherein the metal is Ir or Pt.

8 . The compound of claim 5 , wherein the 2,6-di-substituted aryl group is selected from the group consisting of 2,6-dimethylphenyl; 2,4,6-trimethylphenyl; 2,6-di-isopropylphenyl; 2,4,6-triisopropylphenyl; 2,6-di-isopropyl-4-phenylphenyl; 2,6-dimethyl-4-phenylphenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-diphenylphenyl; 2,6-diphenyl-4-isopropylphenyl; 2,4,6-triphenylphenyl; 2,6-di-isopropyl-4-(4-isopropylphenyl)phenyl; 2,6-di-isopropyl-4-(3,5-dimethylphenyl)phenyl; 2,6-dimethyl-4-(2,6-dimethylpyridin-4-yl)phenyl; 2,6-di-isopropyl-4-(pyridine-4-yl)phenyl; and 2,6-di-(3,5-dimethylphenyl)phenyl.

9 . The compound of claim 1 , wherein any two of R 1a-i may be linked to only form a saturated, or non-aromatic ring.

10 . The compound of claim 2 , wherein the compound is a homoleptic Ir complex.

11 . The compound of claim 2 , wherein the compound is a heteroleptic Ir complex.

12 . The compound of claim 1 , wherein R 1a-i are each independently H, fluoro, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 3 -C 8 cycloalkyl, or substituted or unsubstituted C 6 -C 18 aryl; and the metal is Ir or Pt.

13 . The compound of claim 1 , wherein the bidentate ligand is:

14 . The compound of claim 13 , wherein each of E 1e-o and E 1q is carbon.

15 . The compound of claim 13 , wherein at least one pair of R 1a-i are linked to form a saturated, or non-aromatic ring

16 . The compound of claim 15 , wherein the compound is selected from the group consisting of:

17 . An OLED device comprising the compound of claim 1 .

18 . An OLED device of claim 17 , wherein the metal is Ir or Pt, and R 1b is a 2,6-di-substituted aryl group.

19 . An OLED device of claim 17 , wherein the bidentate ligand is

20 . An OLED device comprising the compound of claim 3 .

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

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1066

  with sulfur · CPC title

• C09K2211/1055

  with other heteroatoms · CPC title

• C09K2211/1081

  with sulfur · CPC title

• C09K2211/1062

  with oxygen · CPC title