Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-11930699-B2
Application number	US-202016983572-A
Country	US
Kind code	B2
Filing date	Aug 3, 2020
Priority date	Aug 15, 2019
Publication date	Mar 12, 2024
Grant date	Mar 12, 2024

Abstract

Provided are compounds comprising a ligand LA of Formula I

First claim

What is claimed is:

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

wherein:
A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are each independently C or N;
K 3 and K 4 are each independently a direct bond, O, or S;
X 1 , X 2 , and X 3 are each independently C or N, at least one of X 1 , X 2 , and X 3 is C;
X is O or NR′;
R A and R B each represents zero, mono, or up to the maximum number of allowed substitutions to its associated ring;
each of R, R′, R A , and R B is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
two adjacent groups can be joined or fused to form a ring wherever chemically feasible, wherein the ligand L A is complexed to a metal M to form a chelate ring as indicated by the two dotted lines;
the metal M can be coordinated to other ligands; and
the ligand L A can be linked with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand.

2. The compound of claim 1 , wherein the compound has Formula II

wherein:
M 1 is Pd or Pt;
rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 3 and Z 4 are each independently C or N;
K 1 , K 2 , K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of them are direct bonds;
L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, absent a bond, O, S, CR″R′″, SiR″R′″, BR″, and NR″,
at least one of L 1 and L 2 is not absent a bond;
X 4 -X 6 are each independently C or N;
R C and R D each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each R″, R′″, R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
two adjacent substituents can be joined or fused together to form a ring wherever chemically feasible.

3. The compound of claim 2 , wherein ring C is a 6-membered aromatic ring.

4. The compound of claim 2 , wherein L 1 is O, CRR′, or NR″.

5. The compound of claim 2 , wherein L 2 is a direct bond.

6. The compound of claim 2 , wherein L 2 is NR″.

7. The compound of claim 2 , wherein K 1 , K 2 , K 3 , and K 4 are each a direct bond.

8. The compound of claim 2 , wherein X 4 -X 5 are both N, and X 6 is C.

9. The compound of claim 2 , wherein L 3 is absent a bond.

10. The compound of claim 2 , wherein L 1 is absent a bond.

11. The compound of claim 2 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L A ′)(Ly) with the following structure:

wherein L A ′ is selected from the group consisting of L A ′1-G to L A ′8-G whose structures are defined in LIST7A
below, L A ″ is selected from the group consisting of L A ″9-G to L A ″16-G whose structures are defined in LIST7A
below, L A ′″ is selected from the group consisting of L A ′″16-G whose structures are defined in LIST7A below,
L A ″″ is selected from the group consisting of L A ″″17-G whose structures are defined in LIST7A below, and
L A ′″″ is selected from the group consisting of L A ′″″18-G whose structures are defined in LIST7A below, and
L A ″″″ is selected from the group consisting of L A ″″″19-G to L A ″″″21-G whose structures are defined in LIST7A below:

LIST7A

Ligand naming convention and structure

L A ′1-G having the structure
L A ′8-G having the structure
L A ″15-G having the structure

L A ′2-G having the structure
L A ″9-G having the structure
L A ″16-G having the structure

L A ′3-G having the structure
L A ″10-G having the structure
L A ′′′16-G having the structure

L A ′4-G having the structure
L A ″11-G having the structure
L A ′′″17-G having the structure

Assignees

• Universal Display Corp

Inventors

• Chen Hsiao-Fan
• Fitzgerald George
• Fleetham Tyler
• Wolohan Peter
• Macor Joseph A
• Macinnis Morgan C
• Palmer Wystan Neil
• Szigethy Geza
• Horwitz Noah

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K85/624

  containing six or more rings · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title