Carbene compounds and organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12577261-B2
Application number	US-202318193678-A
Country	US
Kind code	B2
Filing date	Mar 31, 2023
Priority date	Nov 28, 2017
Publication date	Mar 17, 2026
Grant date	Mar 17, 2026

Abstract

Provided is a compound having Formula I

where rings A and B are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic; together with nitrogen atoms bonded to ring A and ring B, ring W is a 5-membered N-heterocyclic carbene; and the remaining variables are as defined herein.

First claim

We claim:

1 . A compound having Formula I

wherein
X 1 and X 4 can be both C or both N;
X 2 and X 3 are C;
ring A and ring B are each a benzene ring with at least one substituent at ortho position;
L is a monodentate ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Au and Ag; and
each of R A and R B represents mono-substituted or di-substituted alkyl.

2 . The compound of claim 1 , wherein L is selected from the group consisting of:
NR X R Y , PR X R Y , CR X R Y R Z , substituted phenyl, OR X , and SR X , wherein R X , R Y , and R Z are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof, each of which is optionally substituted, or optionally, R X and R Y can join to form five-membered or six-membered, carbocyclic or heterocyclic ring, which is optionally substituted.

3 . The compound of claim 2 , wherein L is NR X R Y and is selected from the group consisting of:
an optionally substituted carbazolyl, or an aza-derivative thereof; an optionally substituted diphenylamino, or an aza-derivative thereof;

wherein R x′ and R y′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, and R k and R 1 are as defined above.

4 . The compound of claim 2 , wherein R X and/or R Y is selected from the group consisting of: an aryl optionally substituted with deuterium, alkyl, or an electron donating substituent group; a heteroaryl optionally substituted with deuterium, alkyl, or an electron donating substituent group; and an alkyl optionally substituted with one or more deuterium atoms.

5 . The compound of claim 1 , with an emission lifetime selected from the group consisting of 0.05 μs to 10 μs, and 0.05 μs to 2 μs, as measured as a polystyrene film at 23° C.

6 . The compound of claim 1 , whose energy separation (ΔE) between the lowest excited singlet state and triplet states is from 10 meV and 150 meV as determined by temperature dependent emission lifetime measurement.

7 . The compound of claim 1 , with an emission spectra spanning from 400 nm to 550 nm as measured in MeCy at RT.

8 . The compound of claim 1 , being an E-type delayed fluorescent emitter.

9 . The compound of claim 1 , wherein the metal is Ag.

10 . The compound of claim 1 , wherein the metal is Au.

11 . The compound of claim 1 , selected from the group consisting of:

12 . An organic electroluminescent device (OLED) that includes an anode, a cathode, and an organic layer comprising a compound having Formula I

wherein
X 1 and X 4 can be both C or both N;
X 2 and X 3 are C;
ring A and ring B are each a benzene ring with at least one substituent at ortho position;
L is a monodentate ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Au and Ag; and
each of R A and R B represents a mono-substituted or di-substituted alkyl.

13 . The OLED of claim 12 , wherein the device emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device, and the luminescent radiation comprises a first radiation component that arises from a delayed fluorescent process or triplet exciton harvesting process.

14 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

15 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

16 . A consumer product comprising an organic light-emitting device (OLED), the OLED including an anode, a cathode, and an organic layer comprising A compound having Formula I

wherein
X 1 and X 4 can be both C or both N;
X 2 and X 3 are C;
ring A and ring B are each a benzene ring with at least one substituent at ortho position;
L is a monodentate ligand with a coordinating member selected from the group consisting of C, N, O, S, and P;
M is a metal selected from the group consisting of Au and Ag; and
each of R A and R B represents a mono-substituted or di-substituted alkyl.

17 . The compound of claim 1 , wherein each of R A and R B is a di-substituted alkyl wherein the di-substituted alkyl is isopropyl.

Assignees

• Univ Southern California

Inventors

• Thompson Mark E
• Djurovich Peter I
• Hamze Rasha
• Shi Shuyang
• Jung Moon Chul

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K85/371

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C07F1/12

  Gold compounds · CPC title

• C07F1/08 Primary

  Copper compounds · CPC title