Luminescent janus-type, two-coordinated metal complexes

Patent metadata

Field	Value
Publication number	US-2021009895-A1
Application number	US-202016901087-A
Country	US
Kind code	A1
Filing date	Jun 15, 2020
Priority date	Jul 12, 2019
Publication date	Jan 14, 2021
Grant date	—

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 I, Formula IIa, or Formula IIb:

wherein each ring A is independently a 5, 6, or 7-membered N-heterocyclic carbene which is condensed with ring B, wherein each ring A may be the same or different;
n is 1, 2, or 3;
ring B is a single or fused saturated or unsaturated carbocyclic or heterocyclic ring which is fused to the n adjacent rings A at arbitrary positions;
ring C in Formula IIa is a 6, 7, or 8-membered N-heterocyclic carbene;
ring C in Formula IIb is a 5, 6, or 7-membered N-heterocyclic carbene;
Q is NR 1 , O, or S;
each occurrence of R 1 is independently alkyl or aryl, wherein R 1 may be further substituted with a substituent selected from the group consisting of 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;
M is Au, Ag, or Cu; and
L is a monoanionic ligand.

2 . The compound of claim 1 , wherein the compound of Formula I is a compound of Formula Ia or Formula Ib:

3 . The compound of claim 1 , wherein ring B is selected from the group consisting of

wherein each occurrence of X is independently N or CR 2 ;
each occurrence of Y is selected from the group consisting of a single bond, O, S, Se, C(R 3 ) 2 , Si(R 3 ) 2 , and NR 3 ;
each occurrence of R 2 and R 3 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;
ring B may be further substituted; and
dashed lines indicate the positions of the ring fusion to ring A.

4 . The compound of claim 1 , wherein ring A selected from the group consisting of

wherein dashed lines indicate the positions of the ring fusion to ring B; and
arrows indicate the coordination site to M.

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

wherein each occurrence of X is independently N or CR 2 ;
each occurrence of Y is selected from the group consisting of a single bond, O, S, Se, C(R 3 ) 2 , Si(R 3 ) 2 , and NR 3 ;
each occurrence of R 2 and R 3 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; ring B may be further substituted.

6 . The compound of claim 1 , wherein L is a monoanionic hydrocarbon, amide, alkoxide, sulfide, or phosphide, which may be optionally further substituted.

7 . The compound of claim 1 , wherein L is selected from the group consisting of:

wherein each occurrence of 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; and
each occurrence of Z is independently C or N.

8 . The compound of claim 1 , wherein ring C in Formula IIb is

wherein arrows indicate coordination sites to M.

9 . A compound of Formula III or Formula IV:

wherein E is a carbene coordinated to metal M;
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 carbocyclic ring or 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 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.

10 . The compound of claim 9 , wherein the compound is a compound of Formula IIIa or Formula IVa

11 . The compound of claim 9 , wherein E is selected from the group consisting of:

wherein each occurrence of 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;
any two adjacent groups R may together join to form a fused ring;
X represents O or S; and
each occurrence of y is independently 1, 2, 3, or 4.

12 . The compound of claim 9 , wherein E is

wherein each occurrence of R′ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino

Assignees

• Univ Southern California

Inventors

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

Classifications

• C07D239/10

  Oxygen or sulfur atoms · CPC title

• C07D233/06

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• H10K2101/10

  Triplet emission · CPC title