Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11196010-B2
Application number	US-201715706186-A
Country	US
Kind code	B2
Filing date	Sep 15, 2017
Priority date	Oct 3, 2016
Publication date	Dec 7, 2021
Grant date	Dec 7, 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.

First claim

We claim:

1. A neutral compound that has a structure of formula (L A ) n Ir(L B ) 3-n ;
wherein L B is a bidentate ligand;
wherein n is 1, 2, or 3; and
wherein ligand L A has a structure 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 , or X 3 is nitrogen;
wherein (a) R 1 is CR 11 R 12 R 13 or joins with R 2 to form into a ring; or
(b) R 2 is not hydrogen, or
(c) both (a) and (b) are true;

wherein R, R 1 , R 2 , R 11 , R 12 , R 13 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein, with the exception of a ring between R and R 2 , any two substituents among R, R 1 , R 2 , R 11 , R 12 , R 13 are optionally joined to form into an aromatic ring;
wherein L A is coordinated to a metal M;
wherein L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein M is optionally coordinated to other ligands; and
wherein L B is C 1 to C 7 alkyl substituted or unsubstituted acetylacetonate.

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

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

4. The neutral compound of claim 1 , wherein X 2 is nitrogen.

5. The neutral compound of claim 1 , wherein R 1 is tert-butyl or substituted tert-butyl.

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

7. The neutral compound of claim 1 , wherein R 2 is selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, and combination thereof.

8. The neutral compound of claim 1 , wherein Ring B is phenyl.

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

wherein X is S or O;
wherein Y is N;
wherein R 1 , R 2 , R 9 , R 10 , R 11 , R 12 , R 13 , and R 14 are each independently selected from the group consisting of hydrogen, deuterium, halogen, 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 substituents are optionally joined to form into a ring.

10. The neutral compound of claim 1 , wherein L B is selected from the group consisting of:

11. The neutral 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 five-membered aromatic ring.

12. The neutral 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 six-membered aromatic ring.

13. The neutral 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

Assignees

• Universal Display Corp

Inventors

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

Classifications

• H10K50/12

  comprising dopants · CPC title

• H10K85/342

  comprising iridium · CPC title

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title