Light-emitting compound

Patent metadata

Field	Value
Publication number	US-11040992-B2
Application number	US-201616063662-A
Country	US
Kind code	B2
Filing date	Dec 15, 2016
Priority date	Dec 18, 2015
Publication date	Jun 22, 2021
Grant date	Jun 22, 2021

Abstract

A compound of formula (I): wherein M is a transition metal; x is at least 1; z is 0 or a positive integer; L1 is a ligand selected from one of ligands (II-A), (II-B); L2 is a ligand selected from another of ligands of formulae (II-A), (II-B) and (II-C); and L3 is a ligand other than a ligand of formulae (II-A), (II-B) or (II-C): (II-A) (II-B) (II-C) in which each of R1-R6 is substituent and Ar1-Ar3 are each an unsubstituted or substituted aryl or heteroaryl group. The compound of formula (I) may be used as a phosphorescent light-emitting material of an organic light-emitting device.

First claim

The invention claimed is:

1. A compound of formula (I):
M ( L 1 ) x ( L 2 ) y ( L 3 ) z   (I)

wherein:
M is a transition metal;
x is at least 1;
y is at least 1;
z is 0 or a positive integer;
L 1 is a ligand of formula (II-A) or (II-B);
L 2 is a ligand of formula (II-C);
and L 3 is a ligand not of formula (II-A), (II-B) or (II-C):

R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in each occurrence is independently a substituent;
Ar 1 , Ar 2 and Ar 3 are each independently an aryl or heteroaryl group that may be unsubstituted or may be substituted with one or more substituents; and
the ligands of formulae (II-A), (II-B) and (II-C), where present in the compound of formula (I), are bound to M by a direct bond between M and nitrogen atom N 1 , N 2 and N 3 respectively and by a direct bond between M and aromatic carbon atom C 1 , C 2 and C 3 respectively.

2. A compound according to claim 1 wherein M is selected from iridium, platinum, osmium, palladium, rhodium and ruthenium.

3. A compound according to claim 2 wherein M is iridium and one of x and y is 1 and the other of x and y is 2.

4. A compound according to claim 1 wherein z is 0.

5. A compound according to claim 1 wherein R 1 , R 3 and R 5 are each independently selected from the group consisting of:
C 1-20 alkyl wherein one or more non-adjacent C atoms of the C 1-20 alkyl may be replaced with —O—, —S—, —NR 8 —, —SiR 8 2 — or COO— and one or more H atoms may be replaced with F wherein R 8 in each occurrence is independently a C 1-20 hydrocarbyl group; and
a group of formula (Ar 4 )n wherein Ar 4 in each occurrence is a C 6-20 aryl group or a 5-20 membered heteroaryl group that may be unsubstituted or substituted with one or more substituents; and n is at least 1.

6. A compound according to claim 1 wherein R 2 , R 4 and R 6 are each independently selected from the group consisting of C 1-20 alkyl and a group of formula —(Ar 5 )m wherein Ar 5 in each occurrence is a C 6-20 aryl group or a 5-20 membered heteroaryl group that may be unsubstituted or substituted with one or more substituents; and m is at least 1.

7. A compound according to claim 1 wherein Ar1, Ar2 and Ar3 are each independently unsubstituted or are substituted with at least one substituent selected from the group consisting of:
C 1-20 alkyl wherein one or more non-adjacent C atoms of the C 1-20 alkyl may be replaced with —O—, —S—, —NR8-, —SiR82- or —COO— and one or more H atoms may be replaced with F wherein R8 in each occurrence is independently a C 1-20 hydrocarbyl group; and
a group of formula —(Ar6)p wherein Ar6 in each occurrence is a C 6-20 aryl group or a 5-20 membered heteroaryl group that may be unsubstituted or substituted with one or more substituents; and p is at least 1.

8. A compound according to claim 1 wherein Ar1, Ar2 and Ar3 are each independently phenyl that may be unsubstituted or substituted with one or more substituents.

9. A compound according to claim 1 , wherein the compound is of formula (III-2) or (III-3):

10. A compound according to claim 9 wherein M is iridium; one of x and y is 1; and the other of x and y is 2.

11. A compound according to claim 1 wherein the compound has a highest occupied molecular orbital energy level in the range of 4.8-5.4 eV.

12. A compound according to claim 1 wherein the compound has a photoluminescent spectrum having a peak wavelength in the range of 400-490 nm.

13. A composition comprising a host material and a compound according to claim 1 .

14. A solution comprising a compound or composition according to claim 1 dissolved in one or more solvents.

15. An organic light-emitting device comprising an anode, a cathode and a light-emitting layer between the anode and cathode wherein the light-emitting layer comprises a compound or composition according to claim 1 .

16. An organic light-emitting device according to claim 15 wherein the device emits white light.

17. A method of forming an organic light-emitting device according to claim 15 comprising the step of depositing the light-emitting layer over one of the anode and cathode, and depositing the other of the anode and cathode over the light-emitting layer.

18. A method according to claim 17 wherein the light-emitting layer is formed by depositing a solution comprising a compound or composition of formula (I):
M ( L 1 ) x ( L 2 ) y ( L 3 ) z   (I)

wherein:
M is a transition metal;
x is at least 1;
y is at least 1;
z is 0 or a positive integer;
L 1 is a ligand of formula (II-A) or (II-B);
L 2 is a ligand of formulae (II-C);
and L 3 is a ligand not of formula (II-A), (II-B) or (II-C):

R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in each occurrence is independently a substituent;
Ar 1 , Ar 2 and Ar 3 are each independently an aryl or heteroaryl group that may be unsubstituted or may be substituted with one or more substituents; and
the ligands of formulae (II-A), (II-B) and (II-C), where present in the compound of formula (I), are bound to M by a direct bond between M and nitrogen atom N 1 , N 2 and N 3 respectively and by a direct bond between M and aromatic carbon atom C 1 , C 2 and C 3 respectively,
dissolved in one or more solvents and evaporating the one or more solvents.

19. A compound according to claim 1 wherein L 1 is a ligand of formula (II-B).

Assignees

• Cambridge Display Tech Ltd
• Sumitomo Chemical Co

Inventors

• Kamtekar Kiran
• Conway Natasha
• Tarran William

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• Y10S428/917

  Electroluminescent · CPC title

• H01L51/0085

  Electricity · mapped topic