Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12281129-B2
Application number	US-202117380482-A
Country	US
Kind code	B2
Filing date	Jul 20, 2021
Priority date	Dec 12, 2018
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

Provided are organometallic compounds including a ligand L A of the following Formula I

Also provided are formulations including these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

First claim

What is claimed is:

1. A compound having the structure of Formula II:

wherein:
ring A and ring B are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
moieties E and F are each independently a monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
M 1 is Pd or Pt;
Z 1 to Z 7 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, C═NR′, C═CR′R″, CR′R″, SiR′R″, BR′, and NR′, wherein at least one of L 1 and L 2 is present;
X is BR 1 , BR 1 R 2 , AlR 1 , AlR 1 R 2 , GaR 1 , GaR 1 R 2 , InR 1 , InR 1 R 2 , CO, SO 2 , or POR 1 ;
Y is NR 3 , NR 3 R 4 , PR 3 , O, S, Se, SO, SO 2 , CR 3 R 4 , SiR 3 R 4 , PR 3 R 4 , or GeR 3 R 4 ;
R A , R B , R E , and R F each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R A , R B , R E , R F , R′, R″, R 1 , R 2 , R 3 , and R 4 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two substituents can be joined or fused together to form a ring.

2. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1 .

3. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1 .

4. A compound comprising a ligand L A of the following Formula IA

wherein:
ring A is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
ring B is a 6-membered carbocyclic or heterocyclic ring:
Z 2 to Z 4 are each independently C or N;
X is BR 1 , AlR 1 , GaR 1 , or InR 1 ;
Y is NR 3 , PR 3 , O, S, Se, CR 3 R 4 , SiR 3 R 4 , or GeR 3 R 4 ;
each of R 1 , R 3 , and R 4 is independently selected from the group consisting of alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, silyl, boryl, aryl, heteroaryl, alkoxy, aryloxy, amino, and combinations thereof;
R A and R B each represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each 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, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
two substituents can be joined to form a ring except that R 1 of BR 1 does not form a 6-membered ring with R 3 of NR 3 when X is BR 1 and Y is NR 3 ;
the ligand L A is coordinated to a metal M by the two indicated dash lines;
the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
one of the following is true;
i) the ligand L A is selected from the group consisting of the following structures:

wherein R A1 and R B1 each represents zero, mono, or up to a maximum allowed substitution to its associated ring;
each of R A1 , R A10 , R A11 , R A12 , R B1 , and R B10 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, or
ii) the ligand L A is selected from the group consisting of: L A 1-(Ri)(Rm)(Rn), L A 2-(Ri)(Rm)(Rn), L A 3-(Ri)(Rm)(Rn), L A 4-(Ri)(Rm)(Rn), L A 5-(Ri)(Rm)(Rn), L A 6-(Ri)(Rn), L A 7-(Ri)(Rn), L A 8-(Ri)(Rn), L A 9-(Ri)(Rn), L A 10-(Ri)(Rn), L A 11-(Ri)(Rn), L A 12-(Ri)(Rn), L A13 -(Ri)(Rn), L A14 -(Ri)(Rn), L A15 -(Ri)(Rm)(Rn)(Rl), L A 16-(Ri)(Rm)(Rn), L A 17-(Ri)(Rm)(Rl), L A 18-(Ri)(Rm)(Rn)(Rl), and L A 19-(Ri)(Rm)(Rn), wherein i, m, n, and l, are each independently an integer from 1 to 70, wherein:

L A
Structure of L A

L A 1-(R1)(R1)(R1) to L A 1-(R70)(R70)(R70) having the structure

L A 2-(R1)(R1)(R1) to L A 2-(R70)(R70)(R70) having the structure

L A 3-(R1)(R1)(R1) to L A 3-(R70)(R70)(R70) having the structure

L A 4-(R1)(R1)(R1) to L A 4-(R70)(R70)(R70) having the structure

L A 5-(R1)(R1)(R1) to L A 5-(R70)(R70)(R70) having the structure

L A 6-(R1)(R1) to L A 6- (R70)(R70) having the structure

Assignees

• Universal Display Corp

Inventors

• Fitzgerald George
• Macor Joseph A
• Brooks Jason
• Chen Hsiao-Fan
• Szigethy Geza
• Drennan Diana
• Palmer Wystan Neil
• Shih Wei-Chun
• Boudreault Pierre-Luc T
• Ji Zhiqiang
• So Woo-Young
• Horwitz Noah

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title