Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11183642-B2
Application number	US-201715825297-A
Country	US
Kind code	B2
Filing date	Nov 29, 2017
Priority date	Oct 3, 2016
Publication date	Nov 23, 2021
Grant date	Nov 23, 2021

Abstract

Novel phosphorescent metal complexes containing ligands having the Formula I:

bearing either a naphthalene or other fused heterocycle moieties such as benzofuran and benzothiophene useful as emitters in OLEDs and improve the device efficiency and the FWHM of the emission are disclosed.

First claim

We claim:

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

wherein Ring B represents a five- or six-membered aromatic ring;
wherein R 3 represents from none to the maximum number of substitutions;
wherein X 1 , X 2 , X 3 , and X 4 are each independently a CR or N;
wherein at least one of X 1 , X 2 , X 3 , or X 4 is N;
wherein at least two adjacent ones of X 1 , X 2 , X 3 , and X 4 are CR and the Rs are fused into a five- or six-membered aromatic ring;
wherein (a) R 1 is CR 15 R 16 R 17 or joins with R 2 to form into a ring; or
(b) at least two adjacent ones of X 1 , X 2 , X 3 , and X 4 are CR and are fused into a furan ring or a thiophene ring, or
(c) both (a) and (b) are true;

wherein R, R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
wherein R 15 , R 16 , and R 17 are each independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof;
wherein any two substituents among R, R 1 , R 2 , and R 3 are optionally joined to form into an aromatic ring;
wherein any two substituents among R 15 , R 16 , and R 17 are optionally joined to form into a ring;
wherein L A is coordinated to a metal M at the positions indicated with dashed lines;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
wherein M is optionally coordinated to other ligands.

2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1 , wherein M is Ir or Pt.

4. The compound of claim 1 , wherein R 1 is tert-butyl, partially or fully deuterated t-butyl, partially or fully fluorinated t-butyl, or a combination of partially deuterated and partially fluorinated t-butyl.

5. The compound of claim 1 , wherein R 1 and R 2 form into an aromatic ring, which can be further substituted.

6. The compound of claim 1 , wherein at least two adjacent ones of X 1 , X 2 , X 3 , and X 4 are CR and are fused into a furan ring or a thiophene ring, and R 2 is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, and combination thereof.

7. The compound of claim 1 , wherein the compound has formula (L A ) n Ir(L B ) 3-n ;
wherein L B is a bidentate ligand; and

n is 1, 2, or 3.

8. The compound of claim 7 , wherein L B is selected from the group consisting of:

9. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
L A391 through L A520 that are based on a structure of Formula III,

in which R 1 , R 9 , R 10 , and Y are defined as provided below:

Ligand
R 1
R 9
R 10
Y

L A391
R B6
H
H
N

L A392
R B6
R B1
H
N

L A393
R B6
R B3
H
N

L A394
R B6
R B4
H
N

L A395
R B6
R B7
H
N

L A396
R B6
R B10
H
N

L A397
R B6
R A3
H
N

L A398
R B6
R A34
H
N

L A399
R B6
H
R B1
N

L A400
R B6
H
R B2
N

L A401
R B6
H
R B3
N

L A402
R B6
H
R B4
N

L A403
R B6
H
R B7
N

L A404
R B6
H
R B10
N

L A405
R B6
H
R A3
N

L A406
R B6
H
R A34
N

L A407
R B6
R B1
R B1
N

L A408
R B6
R B3
R B3
N

L A409
R B6
R B4
R B4
N

L A410
R B6
R B7
R B7
N

L A411
R B6
R B10
R B10
N

L A412
R B6
R A3

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Su Mingjuan
• Wendt Harvey
• Joseph Scott

Classifications

• C07D221/18 Primary

  Ring systems of four or more rings · CPC title

• C07D251/24

  to three ring carbon atoms · CPC title

• C07D209/82

  Carbazoles; Hydrogenated carbazoles · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title