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;
L is an ancillary ligand;
Ring A is selected from the group consisting of;
(a) an 8- to 12-membered bicyclic group having from 3 to 5 ring heteroatoms;
(b) an 11- to 18-membered tricyclic group having from 3 to 6 ring heteroatom;
(c) an 11- to 14-membered fused tricyclic group; and
(d) a 14- to 18-membered fused tetracyclic group;
each RA is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;
a is 0 to 4Ring B is selected from a 5- or 6-membered cyclic group, an 8- to 12-membered bicyclic group, an 11- to 18-membered tricyclic group, an 11- to 14-membered fused tricyclic group, and a 14- to 18-membered fused tetracyclic group;
each RB is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;
b is 0 to 4;
X1 is selected from C—
R1 and N;
X2 is selected from C—
R2 and N;
X3 is selected from C—
R3 and N;
R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;
alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;
additionally or alternatively, R1 and an RB taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group;
additionally or alternatively, R3 and an RA taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group;
each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;
each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl;
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.
1 Assignment
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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.
66 Citations
22 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; L is an ancillary ligand; Ring A is selected from the group consisting of; (a) an 8- to 12-membered bicyclic group having from 3 to 5 ring heteroatoms; (b) an 11- to 18-membered tricyclic group having from 3 to 6 ring heteroatom; (c) an 11- to 14-membered fused tricyclic group; and (d) a 14- to 18-membered fused tetracyclic group; each RA is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;a is 0 to 4 Ring B is selected from a 5- or 6-membered cyclic group, an 8- to 12-membered bicyclic group, an 11- to 18-membered tricyclic group, an 11- to 14-membered fused tricyclic group, and a 14- to 18-membered fused tetracyclic group; each RB is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;b is 0 to 4; X1 is selected from C—
R1 and N;X2 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and an RB taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and an RA taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl;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)
M is a second or third row transition metal; Ring A is selected from the group consisting of; (a) an 8- to 12-membered bicyclic group having from 3 to 5 ring heteroatoms; (b) an 11- to 18-membered tricyclic group having from 3 to 6 ring heteroatom; (c) an 11- to 14-membered fused tricyclic group; and (d) a 14- to 18-membered fused tetracyclic group; each RA is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;a is 0 to 4 Ring B is selected from a 5- or 6-membered cyclic group, an 8- to 12-membered bicyclic group, an 11- to 18-membered tricyclic group, an 11- to 14-membered fused tricyclic group, and a 14- to 18-membered fused tetracyclic group; each RB is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;b is 0 to 4; X1 is selected from C—
R1 and N;X2 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and an RB taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and an RA taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;and each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl.
-
-
6. The device of claim 5, wherein M is Os.
-
7. The device of claim 1, wherein the emissive material has the formula III:
-
wherein; M is a second or third row transition metal; L is an ancillary ligand; Y1 is selected from N and C—
R4;Y2 is selected from N and C—
R5;R4 and R5 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R4 and R5 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R12 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;Z1 is selected from N and C—
R6;Z2 is selected from N and C—
R7;R6 and R7 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R6 and R7 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R22 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;X1 is selected from C—
R1 and N;X2 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and R6 taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and R4 taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl;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.
-
-
8. The device of claim 7, wherein M is Os.
-
9. The device of claim 1, wherein the emissive material has the formula IV:
-
wherein; M is a second or third row transition metal; dotted lines represent optional double bonds; X2 is selected from C—
R2 or N;R2 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R5 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R7 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R12 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;R13 and R14 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively R13 and R14 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R22 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;R23 and R24 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, SO2R′
, SOR′
, SO3k′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively R23 and R24 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)N′
2, CN, CF3, NO2, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;and each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl.
-
-
10. The device of claim 9, wherein M is Os.
-
11. The device according to claim 1, wherein the emissive material is selected from:
-
12. A compound having the formula I:
-
wherein; M is a second or third row transition metal; L is an ancillary ligand; Ring A is selected from the group consisting of; (a) an 8- to 12-membered bicyclic group having from 3 to 5 ring heteroatoms; (b) an 11- to 18-membered tricyclic group having from 3 to 6 ring heteroatom; (c) an 11- to 14-membered fused tricyclic group; and (d) a 14- to 18-membered fused tetracyclic group; each RA is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;a is 0 to 4 Ring B is selected from a 5- or 6-membered cyclic group, an 8- to 12-membered bicyclic group, an 11- to 18-membered tricyclic group, an 11- to 14-membered fused tricyclic group, and a 14- to to 18-membered fused tetracyclic group; each RB is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;b is 0 to 4; X1 is selected from C—
R1 and N;X2 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and an RB taken together form a 5 or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and an RA taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl;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 (13, 14, 15, 16, 17, 18, 19, 20, 21, 22)
M is a second or third row transition metal; Ring A is selected from the group consisting of; (a) an 8- to 12-membered bicyclic group having from 3 to 5 ring heteroatoms; (b) an 11- to 18-membered tricyclic group having from 3 to 6 ring heteroatom; (c) an 11- to 14-membered fused tricyclic group; and (d) a 14- to 18-membered fused tetracyclic group; each RA is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;a is 0 to 4 Ring B is selected from a 5- or 6-membered cyclic group, an 8- to 12-membered bicyclic group, an 11- to 18-membered tricyclic group, an 11- to 14-membered fused tricyclic group, and a 14- to 18-membered fused tetracyclic group; each RB is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;b is 0 to 4; X1 is selected from C—
R1 and N;X2 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and an RB taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and an RA taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;and each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl.
-
-
17. The compound of claim 16, wherein M is Os.
-
18. The compound of claim 12, having the formula III:
-
wherein; M is a second or third row transition metal; L is an ancillary ligand; Y1 is selected from N and C—
R4;Y2 is selected from N and C—
R5;R4 and R5 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R4 and R5 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R12 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;Z1 is selected from N and C—
R6;Z2 is selected from N and C—
R7;R6 and R7 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R6 and R7 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R22 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;X1 is selected from C—
R1 and N;X1 is selected from C—
R2 and N;X3 is selected from C—
R3 and N;R1, R2, and R3 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;alternatively, R1 and R2, or R2 and R3 taken together form a 5- or 6-membered cyclic group, an 8- to 10-membered fused bicyclic group, an 11- to 14-membered fused tricyclic 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively, R1 and R6 taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; additionally or alternatively, R3 and R4 taken together form a 5- or 6-membered cyclic group, or an 8- to 10-membered fused bicyclic group; each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl;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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19. The compound of claim 18, wherein M is Os.
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20. The compound of claim 12, having the formula IV:
-
wherein; M is a second or third row transition metal; dotted lines represent optional double bonds; X2 is selected from C—
R2 or N;R2 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R5 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R7 is 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R12 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;R13 and R14 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively R13 and R14 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;R22 is selected from alkyl, aryl, aralkyl, cycloalkyl and C(O)R′
;R23 and R24 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;additionally or alternatively R23 and R24 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, SO2R′
, SOR′
, SO3R′
, Si(R″
)3, halo, aryl and heteroaryl;each R′
is independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl and heteroaryl;and each R″
is independently selected from H, alkyl, alkenyl, alkynyl and aralkyl.
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-
21. The compound of claim 20, wherein M is Os.
-
22. The compound according to claim 12, having a structure selected from:
Specification
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Current AssigneeUniversal Display Corporation
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Original AssigneeUniversal Display Corporation
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InventorsTsai, Jui-yi, Mackenzie, Peter Borden, WALTERS, Robert W., Beers, Scott
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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 Current313/504
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CPC Class CodesC07F 15/002 Osmium compoundsC09K 11/06 containing organic luminesc...C09K 2211/1014 bridged by heteroatoms, e.g...C09K 2211/1029 containing one nitrogen ato...C09K 2211/185 of the platinum group, i.e....H05B 33/14 characterised by the chemic...Y10S 428/917 Electroluminescent
