ELECTROLUMINESCENT EFFICIENCY
First Claim
Patent Images
1. A compound having the formula:
- wherein M is a metal selected from Ir, Pt, Rh, or Pd;
(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;
wherein R′
5 is an unsubstituted alkyl having 1-15 carbon atoms;
wherein R′
3 is an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and is optionally substituted by one or more substituents Z;
wherein R′
4 and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and each is optionally substituted by one or more substituents Z;
wherein R3, R4, R5, and R6 are 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;
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.
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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 (shown below) wherein an alkyl substituent at position R′5 results in high efficiency and operational stability in the organic light emitting device.
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Citations
20 Claims
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1. A compound having the formula:
-
wherein M is a metal selected from Ir, Pt, Rh, or Pd; (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; wherein R′
5 is an unsubstituted alkyl having 1-15 carbon atoms;wherein R′
3 is an alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and is optionally substituted by one or more substituents Z;wherein R′
4 and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and each is optionally substituted by one or more substituents Z;wherein R3, R4, R5, and R6 are 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; 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.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8)
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-
5. The compound of claim 3, wherein the compound is:
-
6. The compound of claim 1, wherein R3, R4, and R5 are all H.
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7. The compound of claim 1, wherein m=3, n=0, and M is iridium.
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8. The compound of claim 1, wherein R′
- 5 is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, or tert-butyl.
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9. A compound having the formula:
-
wherein M is a metal selected from Ir, Pt, Rh, or Pd; (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; wherein R′
5 is an unsubstituted alkyl having 1-15 carbon atoms;wherein R′
3, R′
4, and R′
6 are each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and each is optionally substituted by one or more substituents Z;wherein R3, R5, and R6 are 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 R7 represents one or more optional substitutions located on any position of ring C, wherein the one or more optional R7 substitutions are all fluoro or all alkyl; 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.- View Dependent Claims (10, 11, 12, 13)
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13. The compound of claim 9, wherein m=3, n=0, and M is iridium.
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14. An organic light emitting device comprising:
-
an anode; a cathode; an organic layer disposed between the anode and the cathode, wherein the organic layer comprises an emissive material; wherein the device produces phosphorescent emission and has an unmodified external quantum efficiency of at least 10% when operated at a current density between 0.1 to 1000 mA/cm2; wherein the emissive material has the formula; wherein M is a metal selected from Ir, Pt, Rh or Pd; (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; wherein R′
5 is an unsubstituted alkyl having 1-15 carbon atoms;wherein R′
3, R′
4, and R′
6 is each independently H, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, or aralkyl, and each is optionally substituted by one or more substituents Z;wherein 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; 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.- View Dependent Claims (15, 16, 17, 18, 19, 20)
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20. The device of claim 14, wherein the emissive material is:
Specification