Electroluminescent efficiency
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Abstract
An organic light emitting device is provided. The device has an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer further includes a molecule of Formula I wherein an alkyl substituent at position R′5 results in high efficiency and operational stability in the organic light emitting device.
44 Citations
73 Claims
- 1. A compound having the formula:
- 2. A compound having the formula:
-
9. A compound having the formula:
- 10. A compound having the formula:
- 22. A compound having the formula
-
27. A compound having the structure:
-
41. An organic light emitting device comprising
an anode a cathode, and an emissive layer disposed between the anode and the cathode wherein the emissive layer comprises an emissive material wherein the emissive layer comprises an emissive material having the formula: -
wherein;
M is a metal selected from Ir, Pt, Rh or Pd;
ring A is an aromatic heterocyclic or a fused aromatic heterocyclic ring having an alkyl substituent at the R′
5 position and having at least one nitrogen atom, N, that is coordinated to the metal M,wherein the ring A can be optionally substituted with one or more substituents at the R′
3, R′
4 and R′
6 positions; and
additionally or alternatively the R′
3 and R′
4 substituted positions on ring A together form, independently a fused ring, wherein the fused ring may be optionally substituted;
ring B is an aromatic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents at the R3, R4, R5 and R6 positions;
R′
3 R′
4 and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, aralkyl; and
wherein R′
3, R′
4, and R′
6 are optionally substituted by one or more substituents Z; and
R3, R4, R5 and R6 is each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, alkylaryl, CN, CO2R, C(O)R, NR2, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl or a heterocyclic group;
wherein at least one of R3, R4, R5 and R6 is a phenyl substituent;
alternatively, R′
3 and R6 may be bridged by a group selected from —
CR2—
CR2—
, —
CR═
CR—
, —
CR2—
, —
O—
, —
NR—
, —
O—
CR2—
, —
NR—
CR2—
, and —
N═
CR—
;
each R is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl;
wherein R is optionally substituted by one or more substituents Z;
each Z is independently a halogen, R′
, OR′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)N(R′
)2, CN, SO2, SOR′
, SO2R′
, or SO3R′
;
Each R′
is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, or heteroaryl;
(X—
Y) is an ancillary ligand;
m is a value from 1 to the maximum number of ligands that may be attached to the metal;
and m+n is the maximum number of ligands that may be attached to the metal. - View Dependent Claims (42, 43, 44, 45, 46, 47, 48)
-
-
49. An organic light emitting device comprising
an anode a cathode, and an emissive layer disposed between the anode and the cathode. wherein the emissive layer comprises an emissive material having the formula: -
wherein;
M is a metal selected from Ir, Pt, Rh or Pd;
ring A is an aromatic heterocyclic or a fused aromatic heterocyclic ring having an alkyl substituent at the R′
5 position and having at least one nitrogen atom, N, that is coordinated to the metal M,wherein the ring A can be optionally substituted with one or more substituents at the R′
3, R′
4 and R′
6 positions; and
additionally or alternatively the R′
3 and R′
4 substituted positions on ring A together form, independently a fused ring, wherein the fused ring may be optionally substituted;
ring B is an aromatic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents at the R3, R4 R5, and R6 positions;
R′
3, R′
4 and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, aralkyl; and
wherein R′
3, R′
4 and R′
6 are optionally substituted by one or more substituents Z; and
wherein at least one of R′
3, R′
4, and R′
6 is not HR3, R4, R5, and R6 is each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, alkylaryl, CN, CO2R, C(O)R, NR2, NO2, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl or a heterocyclic group. alternatively, R′
3 and R6 may be bridged by a group selected from —
CR2—
CR2—
, —
CR═
CR—
, —
CR2—
, —
O—
, —
NR—
, —
O—
CR2—
, —
NR—
CR2—
, and —
N═
CR—
;
each R is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl;
wherein R is optionally substituted by one or more substituents Z;
each Z is independently a halogen, R′
, OR′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)N(R′
)2, CN, SO2, SOR′
, SO2R′
, or SO3R′
;
Each R′
is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, or heteroaryl;
(X—
Y) is an ancillary ligand;
m is a value from 1 to the maximum number of ligands that may be attached to the metal;
and m+n is the maximum number of ligands that may be attached to the metal. - View Dependent Claims (50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60)
-
-
61. An organic light emitting device comprising
an anode a cathode, and an emissive layer disposed between the anode and the cathode. wherein the emissive layer comprises an emissive material having the formula: -
wherein;
M is Ir, Pt, Rh or Pd;
R′
5 is alkyl;
(X—
Y) is an ancillary ligand;
m is a value from 1 to the maximum number of ligands that may be attached to the metal;
and m+n is the maximum number of ligands that may be attached to the metal. - View Dependent Claims (62, 63, 64, 65, 66)
-
-
67. An organic light emitting device comprising
an anode a cathode, and an emissive layer disposed between the anode and the cathode; -
wherein the emissive layer comprises an emissive material having the formula;
wherein M is a metal selected from Ir, Pt, Rh or Pd;
ring A is an aromatic heterocyclic or a fused aromatic heterocyclic ring having an alkyl substituent at the R′
5 position and having at least one nitrogen atom, N, that is coordinated to the metal M,wherein the ring A can be optionally substituted with one or more substituents at the R′
3, R′
4 and R′
6 positions; and
additionally or alternatively the R′
3 and R′
4 substituted positions on ring A together form, independently a fused ring, wherein the fused ring may be optionally substituted;
ring B is an aromatic ring with at least one carbon atom coordinated to metal M, wherein ring B can be optionally substituted with one or more substituents at the R3, R4, R5, and R6 positions;
R′
3 R′
4 and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, aralkyl; and
wherein R′
3 R′
4 and R′
6 are optionally substituted by one or more substituents Z; and
R3 R4 R5 R6 are each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, alkylaryl, CN, CO2R, C(O)R, NR2, NO2, OR, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl or a heterocyclic group such that when R′
3 R′
4 and R′
6 are all H, R3, R4, R5 and R6 are also all H or at least one of R4, R5 and R6 is a phenyl substituent;
alternatively, R′
3 and R6 may be bridged by a group selected from —
CR2—
CR2—
, —
CR═
CR—
, —
CR2—
, —
O—
, —
NR—
, —
O—
CR2—
, —
NR—
CR2—
, and —
N═
CR—
;
each R is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl;
wherein R is optionally substituted by one or more substituents Z;
each Z is independently a halogen, R′
, OR′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)N(R′
)2, CN, SO2, SOR′
, SO2R′
, or SO3R′
;
Each R′
is independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, or heteroaryl;
(X—
Y) is an ancillary ligand;
m is a value from 1 to the maximum number of ligands that may be attached to the metal; and
m+n is the maximum number of ligands that may be attached to the metal - View Dependent Claims (68, 69)
-
-
70. A compound having the structrual formula:
-
71. A ligand having the formuala
-
72. A ligand having the formula:
-
73. A ligand having the formula:
Specification