Luminescent janus-type, two-coordinated metal complexes

Patent metadata

Field	Value
Publication number	US-11920070-B2
Application number	US-202016901087-A
Country	US
Kind code	B2
Filing date	Jun 15, 2020
Priority date	Jul 12, 2019
Publication date	Mar 5, 2024
Grant date	Mar 5, 2024

Abstract

The co-linear or near co-linear structure of bimetallic Janus-type two-coordinated metal complexes may allow for a large transition dipole moment that can enhance the radiative lifetime. The symmetric nature of the bimetallic Janus complexes diminishes or eliminates the polar nature of the monometallic carbene-metal-amide/arene complexes.

First claim

We claim:

1. A compound of Formula III or Formula IV:

wherein E is a carbene coordinated to metal M, wherein E has the structure:

each E can be the same or different;
each ring D is independently a single or fused carbocyclic ring or heterocyclic ring, which may be saturated or unsaturated, which is bound covalently bound to Z, wherein each ring D may be the same or different, and wherein each ring D is independently substituted with R;
Z is a linking group selected from the group consisting of a single bond, aryl, heteroaryl, alkyl, O, S, NR, and combinations thereof;
m is 2, 3, or 4;
G is a single or fused heterocyclic ring, which may be saturated or unsaturated; which comprises m atoms Q; and which may be optionally substituted with one or more R,
each occurrence of R and R′ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
each occurrence of Q is independently C or N; and
M is Au, Ag, or Cu.

2. The compound of claim 1 , wherein the compound is a compound of Formula Ma or Formula IVa

3. The compound of claim 1 , wherein m is 2.

4. The compound of claim 1 , wherein G is selected from the group consisting of

wherein dashed lines indicate coordination to the metal M;
X is O, S, or C(R 6 ) 2 ;
Y is O, S, or C(R 6 ) 2 ;
each occurrence of R 6 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and two R 6 may optionally together form a ring.

5. The compound of claim 1 , wherein each D is independently selected from the group consisting of phenyl, fluorene, naphthalene, triphenylene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, and benzimidazole.

6. The compound of claim 2 , wherein

is represented by

wherein arrows indicate coordination to the metal M;
Y is O, S, SO, SO 2 , NR 7 , or C(R 7 ) 2 ;
each occurrence of R 7 is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and two R 7 may optionally together form a ring.

7. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound according to claim 1 .

8. A formulation comprising the compound of claim 1 .

Assignees

• Univ Southern California

Inventors

• Djurovich Peter I
• Thompson Mark E
• Ukwitegetse Narcisse
• Li tian-yi
• Hamze Rasha

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D233/06

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C07D239/10

  Oxygen or sulfur atoms · CPC title

• H10K85/361

  Polynuclear complexes, i.e. complexes comprising two or more metal centers · CPC title

• H10K85/371

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