Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10121975-B2
Application number	US-201414302042-A
Country	US
Kind code	B2
Filing date	Jun 11, 2014
Priority date	Jul 3, 2013
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A compound comprising a ligand L A selected from:

as well as, devices and formulations containing the compound are disclosed. In the compounds, independently X 1 -X 6 are CH or N; Y 1 -Y 12 are independently selected from CH, N, and C-APR 1 ′R 1 ″; when present, exactly one of Y 1 through Y 12 is C-APR 1 ′R 1 ″ in L A8 ; A is selected from a single bond, —CR A R B —, —NR A —, —O—, —S— and —SiR A R B —; and R, R 1 ′, R 1 ″, R 2 , R 3 , R A , and R B are each independently a substituent selected from hydrogen, deuterium, alkyl, cycloalkyl, aryl, and combinations thereof. The P-atom of the ligand L A is bonded to a metal M having an atomic weight of at least 40.

First claim

We claim:

1. A compound comprising a metal and a ligand L A selected from the group of ligands consisting of:

wherein Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , Y 8 , Y 9 , Y 10 , Y 11 , and Y 12 are independently selected from the group consisting of CH, C bonded to metal M, N, and C-APR 1 ′R 1 ″, and the ligand L A is bidentate with a first bond to the metal M formed with the P-atom of the C-APR 1 ′R 1 ″ and a second bond to the metal M formed with a ring carbon of ligand L A5 , ligand L A6 , ligand L A7 , or ligand L A8 ; wherein the metal M has an atomic weight of at least 40;
wherein exactly one of Y 1 through Y 8 is C-APR 1 ′R 1 ″ in L A5 and L A6 , and exactly one of Y 1 through Y 8 is the ring carbon bonded to the metal;
wherein exactly one of Y 1 through Y 10 is C-APR 1 ′R 1 ″ in L A7 , and exactly one of Y 1 through Y 10 is the ring carbon bonded to the metal;
wherein exactly one of Y 1 through Y 12 is C-APR 1 ′R 1 ″ in L A8 , and exactly one of Y 1 through Y 12 is the ring carbon bonded to the metal;
wherein A is selected from the group consisting of a single bond, —CR A R B —, —NR A —, —O—, —S— and —SiR A R B —;
wherein R, R 1 ′, R 1 ″, R 2 , R 3 , R A , and R B are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl.

2. The compound of claim 1 , wherein M is a metal selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1 , wherein R 1 ′ and R 1 ″ are each phenyl.

4. The compound of claim 1 , wherein the compound has the formula M(L A ) m (L B ) n , wherein the ligand L B is a different ligand from the ligand L A ;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M; and m+n is the maximum number of ligands that may be coordinated to the metal M, and the ligand L B is selected from the group of ligands consisting of:

wherein:
X 7 , X 8 , X 9 , and X 10 are independently selected from the group consisting of CH, and N;
X 11 , X 12 , and X 13 are independently selected from the group consisting of CH, CR′, and N;
R a , R b , and R c , may represent mono, di, tri, or tetra substitution, or no substitution;
R d may represent mono, di, or tri substitution, or no substitution;
R′, R a , R b , R c , R d are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acids, ester, nitrile, isonitrile, and phosphino; and
two adjacent substituents of R a , R b , R c , and R d are optionally joined to form a fused ring;
wherein dotted arcs of ligand L B28 and ligand L B29 represent optional fused rings, which can be cyclic, heterocyclic, aromatic, or heteroaromatic, and which can be further substituted; and
if present, each end of each dotted arc is fused to a carbon atom.

5. The compound of claim 1 , wherein the compound has the formula M(L A ) x (L B ) y (LC) z ,
wherein the ligands L A , L B and L C are three different ligands, and L C is a monodentate ligand;
x is 1, or 2;
y is 0, 1, or 2;
z is 0, 1, or 2; and
wherein x+y+z is the oxidation state of the metal M.

6. The compound of claim 1 , wherein the compound is homoleptic.

7. The compound of claim 6 , wherein the compound has a facial configuration.

8. The compound of claim 6 , wherein the compound has a meridional configuration.

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

10. The compound of claim 9 , wherein the second bond between the metal and the ligand L A is formed by:
a carbon atom of Ring 2 of the ligands L A5-1 and L A6-1 .

11. The compound of claim 1 , wherein the compound has the formula M(L A ) m (L B ) n , wherein the ligand L B is a different ligand from the ligand L A ;
wherein m is an integer from 1 to the maximum number of ligands that may be coordinated to the metal M; and m+n is the maximum number of ligands that may be coordinated to the metal M, and the ligand L B is selected from the group of ligands consisting of:

wherein:
X 7 , X 8 , X 9 , and X 10 are independently selected from the group consisting of CH, and N;
X 11 , X 12 , and X 13 are independently selected from the group consisting of CH, CR′, and N;
R a , R b , and R c , may represent mono, di, tri, or tetra substitution, or no substitution;
R′, R a , R b , and R c are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carboxylic acids, ester, nitrile, isonitrile, and phosphino; and
two adjacent substituents of R a , R b , and R c are optionally joined to form a fused ring;
wherein dotted arcs of ligand L B29 represent optional fused rings, which can be cyclic, heterocyclic, aromatic, or heteroaromatic, and which can be further substituted; and
if present, each end of each dotted arc is fused to a carbon atom.

12. The compound of claim 11 , where the compound is selected from the group consisting of:

wherein

is selected from the group consisting of L B1 through L B10 , L B12 through L B25 , and L B29 ,
wherein each R 1 is independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, and aryl, and
wherein n=0, 1, or 2.

13. A first device comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a metal and a ligand L A selected from the group of ligands consisting of:

Assignees

• Univ Southern California
• Universal Display Corp

Inventors

• Thompson Mark E
• Liu Yifei
• Djurovich Peter I

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• C09K2211/185

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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic