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;
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.
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Accused Products
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.
1177 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; 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. - 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)
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; ring A selected from a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, wherein ring A 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 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;each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;n is 1 or 2; m is 0 to 3, wherein when n is 1, m is 1 to 3, and when n is 2, m is 0.
-
-
8. The device of claim 7, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
9. The device of claim 8, wherein M is selected from Os and Ru.
-
10. The device of claim 9, wherein M is Os.
-
11. The device of claim 7, wherein the emissive material has the formula III:
-
wherein M is a second or third row transition metal; the dotted lines represent optional double bonds; X1 is selected from C and N; X2 is selected from C, N, O, S and P; X3 is selected from C and N; ring A selected from a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, wherein ring A 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 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;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 Z1 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.
-
-
12. The device of claim 11, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
13. The device of claim 12, wherein M is selected from Os and Ru.
-
14. The device of claim 13, wherein M is Os.
-
15. The device of claim 1, wherein the emissive material has the formula IV:
-
wherein M is a second or third row transition metal; the dotted lines represent optional double bonds; X1 is selected from C and N; X2 is selected from C and N; X3 is selected from C and N; 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; R 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;R7, R8 and R9 are 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; and
additionally or alternatively, R5 and R6 or R6 and R7 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group optionally contains 1 to 3 ring heteroatoms and is optionally substituted with one of more substituents 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 R7 taken together with the atoms to which they are attached 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 R9 taken together with the atoms to which they are attached 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.
-
-
16. The device of claim 15, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
17. The device of claim 16, wherein M is selected from Os and Ru.
-
18. The device of claim 17, wherein M is Os.
-
19. The device of claim 1, wherein the emissive material has the formula V:
-
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 and N; X3 is selected from C and N; ring A selected from a 5- or 6-membered cyclic group or a 8- to 10-membered fused bicyclic group, wherein ring A 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;ring B and ring C are independently selected from 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 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; Z1 is C or N; Z2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;n is 1 or 2; m is 0 to 3, wherein when n is 1, m is 1 to 3, and when n is 2, m is 0.
-
-
20. The device of claim 19, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
21. The device of claim 20, wherein M is selected from Os and Ru.
-
22. The device of claim 21, wherein M is Os.
-
23. The device of claim 1, wherein the emissive material has the formula VI:
-
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 and N; X3 is selected from C and N; ring B and ring C are independently selected from 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 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; Z1 is C or N; Z2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N; R7, R8 and R9 are 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; and
additionally or alternatively, R5 and R6 or R6 and R7 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group optionally contains 1 to 3 ring heteroatoms and is optionally substituted with one of more substituents 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; m is 0 to 3, wherein when n is 1, m is 1 to 3, and when n is 2, m is 0.
-
-
24. The device of claim 23, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
25. The device of claim 24, wherein M is selected from Os and Ru.
-
26. The device of claim 25, wherein M is Os.
-
27. The device of claim 1, wherein the emissive material has the formula VII:
-
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 and N; X3 is selected from C and N; ring B and ring C are independently selected from 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 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; Z1 is C or N; Z2 is C, N, O, S or P, wherein when Y1 is N, Y2 is C or N; R7, R8 and R9 are 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; and
additionally or alternatively, R5 and R6 or R6 and R7 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group optionally contains 1 to 3 ring heteroatoms and is optionally substituted with one of more substituents 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.
-
-
28. The device of claim 27, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
29. The device of claim 28, wherein M is selected from Os and Ru.
-
30. The device of claim 29, wherein M is Os.
-
31. The device of claim 1, wherein the emissive material has the formula VIII
wherein: -
M is a second or third row transition metal; X2 is selected from C or N; Q is a bond or —
C(R′
)2—
;R7, R8 and R9 are 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; and
additionally or alternatively, R5 and R6 or R6 and R7 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group optionally contains 1 to 3 ring heteroatoms and is optionally substituted with one of more substituents 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;R12 is selected from alkyl, aryl and aralkyl; R10 and R11 are independently selected from H, 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 R10 and R11, or R11 and R12 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group is optionally substituted with one of more substituents 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;R22 is selected from alkyl, aryl and aralkyl; R20 and R21 are independently selected from H, 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; andadditionally or alternatively R20 and R21, or R21 and R22 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group is optionally substituted with one of more substituents 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; andeach R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl.
-
-
32. The device of claim 31, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
33. The device of claim 32, wherein M is selected from Os and Ru.
-
34. The device of claim 33, wherein M is Os.
-
35. The device of claim 1, wherein the emissive material has the formula X:
-
wherein; M is a second or third row transition metal; Y2 and Z2 are independently selected from C and N; R8, R9, R13, R14, R15, R16, R25, and R26 are independently selected from H 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 R8 and R9 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group is optionally substituted with one of more substituents 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 R13 and R14, or R14 and R5, or R15 and R16 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group is optionally substituted with one of more substituents 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; andadditionally or alternatively R23 and R24, or R24 and R25, or R25 and R26 form a fused 5- or 6-membered cyclic group, wherein the fused cyclic group is optionally substituted with one of more substituents 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; andeach R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl.
-
-
36. The device of claim 35, wherein M is selected from Ru, Os, Re, Rh, Ir, Pd and Pt.
-
37. The device of claim 36, wherein M is selected from Os and Ru.
-
38. The device of claim 37, wherein M is Os.
Specification