Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12473318-B2
Application number	US-202217656885-A
Country	US
Kind code	B2
Filing date	Mar 29, 2022
Priority date	Oct 8, 2021
Publication date	Nov 18, 2025
Grant date	Nov 18, 2025

Abstract

Provided are organometallic compounds based on platin or palladium and their various uses including as emitters in devices having the structure of Formula I comprising at least four rings as defined herein. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices and related consumer products that utilize these compounds.

First claim

What is claimed is:

1 . A compound of Formula I:

wherein
rings C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
Z 1 and Z 2 are independently C or N;
K 1 , K 2 , K 3 , and K 4 are each independently a direct bond, O, or S;
at least two of K 1 , K 2 , K 3 , and K 4 are a direct bond;
X 1 -X 8 , X 21 , and X 22 are each independently C or N;
L is selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′;
L 1 , L 2 , and L 3 are each independently a direct bond, a single atom linker, or a two atom linker selected from the group consisting of BR, BRR′, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, GeRR′, and combinations thereof,
at least one of conditions (1), (2), (3), (4), (5), (6) or (7) is met:
(1) at least two of X 1 -X 8 are N;
(2) X 1 and X 8 are both C, and at least one of X 2 —X 7 is N;
(3) X 1 and X 8 are both C, and one of K 1 and K 2 is not a direct bond;
(4) at least one of K 1 , K 2 , K 3 , and K 4 is not a direct bond;
(5) ring D is a six-membered ring and comprises at least one N that is not Z 2 ;
(6) L 2 is present and is not a direct bond;
(7) rings C and D are each independently a 6-membered carbocyclic or heterocyclic ring;
a, b, and c are each independently 0 or 1;
a+b+c=2 or 3;
X 2 is C if a=1 and L 1 is selected from the group consisting of BR, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′, and X 7 is C if c=1 and L 3 is selected from the group consisting of BR, NR, PR, O, S, Se, C═R″, CRR′, SiRR′, and GeRR′; X 1 , X 8 , Z 1 , and Z 2 are C if bonded to O or S;
R A , R B , R C , and R D each independently represent mono to the maximum allowable substitution, or no substitution;
each R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof,
each R″ is independently selected from the group consisting of O, S, NR and CRR′
M is Pt or Pd; and

any two adjacent R, R′, R A , R B , R C , and R D can be joined or fused to form a ring; and
with the proviso that the compound does not comprise Formula II:

wherein R 1 and R 2 are each independently alkyl or aryl; L X is a direct bond, CR X R X , or NR X ; L Y is a direct bond or NR X ; R X is an aryl group that does not connect to ring X, ring Y, or ring Z; and Z 1 and Z 2 are C or N.

2 . The compound of claim 1 , wherein at least one of X 1 and X 8 is N.

3 . The compound of claim 1 , wherein X 1 and X 8 are both C, and at least one of X 2 -X 7 is N.

4 . The compound of claim 1 , wherein X 1 and X 1 are both C, and one of K 1 and K 2 is not a direct bond.

5 . The compound of claim 1 , wherein at least one of K 1 , K 2 , K 3 , and K 4 is not a direct bond.

6 . The compound of claim 1 , wherein L 2 is present and is not a direct bond.

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

8 . The compound of claim 1 , wherein one of K 1 , K 2 , K 3 , and K 4 is O.

9 . The compound of claim 1 , wherein at least one of rings C and D is a 6-membered carbocyclic or heterocyclic ring.

10 . The compound of claim 1 , wherein L is CRR′.

11 . The compound of claim 1 , wherein L is O.

12 . The compound of claim 1 , wherein each R, R′, R A , R B , 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.

13 . The compound of claim 1 , wherein Z 2 is N and Z 1 is C, or wherein Z 2 is C and Z 1 is N.

14 . The compound of claim 1 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L A′ )(Ly):

wherein L A′ is selected from the group consisting of the structure shown below:

wherein L y is selected from the group consisting of the structures shown below:

15 . The compound of claim 1 , wherein the compound is selected from the group consisting of the compounds having the formula of Pt(L A′ )(Ly):

wherein L A′ is selected from the group consisting of the structures shown below:

Ligand L A′
Structure of L A′

L A′ 1-(R l )(R m )(R n )(L o ), wherein l, m, and n are each an integer from 1 to 309, wherein L A′ 1-(R1)(R1)(R1)(L1) to L A′ 1-(R309)(R309)(R309)(L15), having the structure

L A′ 2-(R l )(R m )(R n )(L o ), wherein l, m, and n are each an integer from 1 to 309, wherein L A′ 2-(R1)(R1)(R1)(L1) to L A′ 2-(R309)(R309)(R309)(L15), having the structure

L A′ 3-(R l )(R m )(R n )(L o ), wherein l, m, and n are each an integer from 1 to 309, wherein L A′ 3-(R1)(R1)(R1)(L1) to L A′ 3-(R309)(R309)(R309)(L15), having the structure

Assignees

• Universal Display Corp

Inventors

• Jradi Fadi M
• Chen Hsiao-Fan
• Thompson Nicholas J
• Fleetham Tyler

Classifications

• H10K85/346

  comprising platinum · CPC title

• H10K85/6572

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

• H10K85/6576

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title