Complexes with tridentate ligands
First Claim
Patent Images
1. An organic light emitting device, comprising:
- an anode;
a cathode; and
a phosphorescent emissive region disposed between the anode and the cathode, wherein the emissive region comprises an emissive material having the formula I;
wherein;
M is a second or third row transition metal;
the dotted lines represent optional double bonds;
L is an ancillary ligand;
X1 is selected from C and N;
X2 is selected from C, N, O, S and P;
X3 is selected from C and N;
each Q is independently selected from a chemical bond and —
C(R′
)2—
;
Y1 is C or N;
Y2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N;
R1 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
a is 1 or 2;
R3 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
c is 1 or 2;
alternatively, R1 and R3, taken together with Y1 and Y2, form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
Z1 is C or N;
Z2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N;
R2 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
b is 1 or 2;
R4 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
d is 1 or 2;
alternatively, R2 and R4, taken together with Z1 and Z2, form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
R5 and R6 are independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
or alternatively, R5 and R6, taken together with X1, X2 and X3 form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
additionally or alternatively R1 and R5 taken together with X1, Q and Y1 form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
additionally or alternatively R2 and R6 taken together with X3, Q and Z′
form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;
n is 1 or 2; and
m is 0 to 3, wherein when n is 1, m is 1 to 3, and when n is 2, m is 0;
wherein at least one of X2, Y2 or Z2 is C and is selected to be a carbene donor.
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Abstract
The present invention relates to organic light emitting devices (OLEDs), and more specifically to phosphorescent organic materials used in such devices. More specifically, the present invention relates to emissive phosphorescent material which comprise at least one tridentate ligand bound to a metal center, wherein at least one of the bonds to the tridentate ligand is a carbon-metal bond.
711 Citations
38 Claims
-
1. An organic light emitting device, comprising:
-
an anode;
a cathode; and
a phosphorescent emissive region disposed between the anode and the cathode, wherein the emissive region comprises an emissive material having the formula I;
wherein;
M is a second or third row transition metal;
the dotted lines represent optional double bonds;
L is an ancillary ligand;
X1 is selected from C and N;
X2 is selected from C, N, O, S and P;
X3 is selected from C and N;
each Q is independently selected from a chemical bond and —
C(R′
)2—
;
Y1 is C or N;
Y2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N;
R1 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
a is 1 or 2;
R3 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
c is 1 or 2;
alternatively, R1 and R3, taken together with Y1 and Y2, form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
Z1 is C or N;
Z2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N;
R2 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
b is 1 or 2;
R4 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
d is 1 or 2;
alternatively, R2 and R4, taken together with Z1 and Z2, form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
R5 and R6 are independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, C(O)R′
, C(O)OR′
, C(O)NR′
2, aryl and heteroaryl;
or alternatively, R5 and R6, taken together with X1, X2 and X3 form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
additionally or alternatively R1 and R5 taken together with X1, Q and Y1 form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
additionally or alternatively R2 and R6 taken together with X3, Q and Z′
form a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, which may be optionally substituted with one or more substituents independently selected from alkyl, alkenyl, alkynyl, aralkyl, O—
R′
, N(R′
)2, SR′
, C(O)R′
, C(O)OR′
, C(O)NR′
2, CN, CF3, NO2, SO2, SOR′
, or SO3R′
halo, aryl and heteroaryl;
each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;
n is 1 or 2; and
m is 0 to 3, wherein when n is 1, m is 1 to 3, and when n is 2, m is 0;
wherein at least one of X2, Y2 or Z2 is C and is selected to be a carbene donor. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38)
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Current AssigneeUniversal Display Corporation, University of Southern California
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Original AssigneeUniversity of Southern California
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InventorsTsai, Jui-Yi, Thompson, Mark E., Walters, Robert, MacKenzie, Peter B.
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current428/690
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CPC Class CodesC09K 11/06 containing organic luminesc...C09K 2211/1044 containing two nitrogen ato...C09K 2211/185 of the platinum group, i.e....H05B 33/14 characterised by the chemic...H10K 2101/10 Triplet emissionH10K 50/11 characterised by the electr...H10K 85/348 comprising osmium
