Carbene compounds and organic electroluminescent devices

Patent metadata

Field	Value
Publication number	US-12180230-B2
Application number	US-201816191604-A
Country	US
Kind code	B2
Filing date	Nov 15, 2018
Priority date	Nov 28, 2017
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

Abstract

A compound selected from the group consisting of Formula I, Formula II, and Formula III,whereinring A, ring B, and ring C are independently a five-membered or six-membered, carbocyclic or heterocyclic ring, each of which is optionally aromatic;ring W of Formula I is a 6-membered heterocyclic ring, and ring W of Formula II or Formula III is a 5-membered or 6-membered heterocyclic ring;L is a monodentate ligand with a metal coordinating member selected from the group consisting of C, N, O, S, and P; andM is a metal selected from the group consisting of Cu, Au, and Ag.

First claim

The invention claimed is:

1. A compound selected from the group consisting of Formula I and Formula III,

wherein
L is a monodentate anionic 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 Cu, Au, and Ag;
each of R 1 and R 2 is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, cycloalkenyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted;
wherein R 1 and R 2 are further joined to form a single carbocyclic ring with an optional heteroatom, wherein the carbocyclic ring does not include an unsubstituted cyclohexyl ring or an adamantyl ring;
each of R A and R B independently represent mono to the maximum allowable substitution, or no substitution, and
each R A and R B is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
or optionally, any two adjacent R A or R B can join to form a ring, which is optionally substituted;
one of Y 1 and Y 2 is C═O and the other of Y 1 and Y 2 is CRR′ or C═O, wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, or optionally, R and R′ can be joined to form a ring, which is optionally substituted;
L is selected from the group consisting of: NR X R Y , PR X R Y , CR X R Y R Z , phenyl, 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; and
wherein in Formula I, when L is a substituted phenyl, the substitution is not two methyl groups at both ortho positions, and
in Formula III, when L is OR X , R X is not butyl; and when L is CR X R Y R Z , R X , R Y , and R Z are not methyl.

2. The compound of claim 1 , selected from the group consisting of Formula 1A and Formula 1B

3. The compound of claim 1 , 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′ , R Y′ , and R N 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 l are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, and combinations thereof.

4. The compound of claim 1 , 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 of 0.05 μs to 10 μs, as measured as a polystyrene film at 23° C.

6. The compound of claim 1 with an energy separation (ΔE) of 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 390 nm to 850 nm as measured as a polystyrene film at 23° C.

8. The compound of claim 1 , with maximum emission wavelength (λ max ) of from 432 nm to 666 nm as measured as a polystyrene film at 23° C.

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

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

11. An organic electroluminescent device (OLED) that includes an anode, a cathode, and an organic layer comprising a compound selected from the group consisting of Formula I and Formula III,

wherein
L is a monodentate anionic 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 Cu, Au, and Ag;
each of R 1 and R 2 is independently selected from the group consisting of hydrogen,
deuterium, fluorine, alkyl, cycloalkyl, cycloalkenyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; each of which is optionally substituted;
wherein R 1 and R 2 are further joined to form a single carbocyclic ring with an optional heteroatom, wherein the carbocyclic ring does not include an unsubstituted cyclohexyl ring or an adamantyl ring;
each of R A and R B independently represent mono to the maximum allowable substitution, or no substitution, and
each R A and R B is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
or optionally, any two adjacent R A or R B can join to form a ring, which is optionally substituted;
one of Y 1 and Y 2 is C═O and the other of Y 1 and Y 2 is CRR′ or C═O, wherein R and R′ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof, or optionally, R and R′ can be joined to form a ring, which is optionally substituted;
L is selected from the group consisting of: NR X R Y , PR X R Y , CR X R Y R Z , phenyl, 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; and
wherein in Formula I, when L is a substituted phenyl, the substitution is not two methyl groups at both ortho positions, and in Formula III, when L is OR X , R X is not butyl; and when L is CR X R Y R Z , R X , R Y , and R Z are not methyl.

12. The OLED of claim 11 , 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 radia

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