Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11081658-B2
Application number	US-202016828080-A
Country	US
Kind code	B2
Filing date	Mar 24, 2020
Priority date	Oct 3, 2016
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

A novel compound is disclosed which includes a ligand LA of Formula I, Formula II, Formula III, or Formula IV:wherein:ring B is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring; X1 to X4 are each independently selected from the group consisting of C, N, and CR;at least one pair of adjacent X1 to X4 are each C and fused to a structure of Formula Vwhere indicated by “”; X5 to X12 are each independently C or N; the maximum number of N within a ring is two; Z and Y are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, SiR′R″, and GeR′R″; RB and RC each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring; each of RB, RC, R, R′, and R″ is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and two substituents can be joined or fused to form a ring; the ligand LA is complexed to a metal M through the two indicated dash lines of each Formula; and the ligand LA can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

First claim

What is claimed is:

1. A compound comprising a ligand L A of Formula I, Formula II, Formula III, or Formula IV:

wherein:
ring B is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
X 1 to X 4 are each independently selected from the group consisting of C and CR;
at least one pair of adjacent X 1 to X 4 are each C and fused to a structure of Formula V

where indicated by “ ”;
X 5 to X 8 are each independently C or N;
each of X 9 to X 12 is C;
Z and Y are each independently selected from the group consisting of O, S, Se, NR′, CR′R″, SiR′R″, and GeR′R″;
R B and R C each independently represents zero, mono, or up to a maximum allowed substitutions to its associated ring;
each of R B , R C , R, R′, and R″ is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and two substituents can be joined or fused to form an aromatic ring;
the ligand L A is complexed to a metal M through the two indicated dash lines of each Formula; and
the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

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

3. The compound of claim 1 , wherein ring B is a 6-membered ring.

4. The compound of claim 1 , wherein each of X 1 to X 4 is independently C or CR.

5. The compound of claim 1 , wherein each of X 5 to X 8 is C.

6. The compound of claim 1 , wherein at least one of X 5 to X 8 in each formula is N.

7. The compound of claim 1 , wherein Z for each occurrence is independently O or S.

8. The compound of claim 1 , wherein at least one R B in each formula is independently an alkyl or cycloalkyl group.

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

10. The compound of claim 1 , wherein the metal M is selected from the group consisting of Os, Ir, Pd, Pt, Cu, Ag, and Au.

11. The compound of claim 1 , wherein the compound comprises the ligand L A selected from the group consisting of:

wherein each of R B can be the same or different, each of R C can be the same or different, and
R B and R c for each occurrence is independently selected from deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfanyl, sulfonyl, phosphino, boryl, and combinations thereof.

12. The compound of claim 1 , wherein the compound comprises the ligand L A selected from the group consisting of
L Ai-1 based on Structure 1:

L Ai-2 based on Structure 2:

L Ai-3 based on Structure 3:

L Ai-4 based on Structure 4:

L Ai-5 based on Structure 5:

L Ai-6 based on Structure 6:

L Ai-7 based on Structure 7:

L Ai-8 based on Structure 8:

L Ai-9 based on Structure 9:

L Ai-10 based on Structure 10:

L Ai-11 based on Structure 11:

L Ai-12 based on Structure 12:

L Ai-13 based on Structure 13:

L Ai-14 based on Structure 14:

L Ai-15 based on Structure 15:

L Ai-16 based on Structure 16:

L Ai-17 based on Structure 17:

L Ai-18 based on Structure 18:

L Ai-19 based on Structure 19:

L Ai-20 based on Structure 20:

L Ai-21 based on Structure 21:

L Ai-22 based on Structure 22:

L Ai-23 based on Structure 23:

L Ai-24 based on Structure 24:

L Ai-25 based on Structure 25:

L Ai-26 based on

Assignees

• Universal Display Corp

Inventors

• Boudreault Pierre-Luc T
• Alleyne Bert
• Ji Zhiqiang

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• H10K85/342

  comprising iridium · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C07F15/0033

  Iridium compounds · CPC title