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US 7,279,704 B2Granted
Complexes with tridentate ligands
AssigneesUniversity of Southern California, Universal Display Corporation
InventorsRobert Walters, Jui-Yi Tsai, Peter B. MacKenzie, Mark E. Thompson
Life of this patent
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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.
Claims38
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:
- at least one of X2, Y2 and Z2 is a carbene carbon, forming a carbene-metal bond with M;
- 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.
33 more elements
Dependencies are inferred from the claim text.