Organic electroluminescent devices
An organic light emitting device is disclosed in which the emissive dopant material in its organic emissive layer is an organic phosphorescent emissive material and a neat film of the organic phosphorescent emissive material is disposed between the organic emissive layer and the anode as an electron blocking layer.
1. An organic light emitting device comprising:
an anode;
a cathode;
an organic light emissive layer disposed between the anode and the cathode, wherein the organic emissive layer comprises one or more host material and an organic phosphorescent emissive dopant material; and
an electron blocking layer comprising a neat film of the organic phosphorescent emissive dopant material disposed between the organic emissive layer and the anode.
2. The device of claim 1 , wherein the electron blocking layer is a neat film of the organic phosphorescent emissive dopant material.
3. The device of claim 1 , wherein the organic phosphorescent emissive dopant material is a carbene based compound having a carbene ligand coordinated to a metal center.
4. The device of claim 3 , wherein the carbene based compound has the structure:
wherein M is a metal; ring D is an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring,
wherein ring D can be optionally substituted with one or more substitutents R 2 ;
R 1 and R 2 are independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, CN, CF 3 , CO 2 R′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, SO 3 R′, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R 3 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and additionally or alternatively, two R groups on the same or adjacent ring, together may form independently a 5 or 6-member cyclic group, which is a cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl; and wherein said cyclic group may be substituted by one or more substituents J;
each substituent J is independently selected from the group consisting of R′, CN, CF 3 , C(O)OR′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, or SO 3 R′, and additionally, or alternatively, two J groups on adjacent ring atoms may form a fused 5- or 6-membered aromatic group;
each R′ is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
Z 1 and Z 2 are selected from a bond, O, S, or NR′;
A 1 , A 2 , A′, and A″ are independently selected from C, N, or P;
(X—Y) is selected from a photoactive ligand or an ancillary ligand;
a is 0, 1, 2, 3, or 4;b is 0, 1, or 2;
m is a value from 1 to the maximum number of ligands that may be attached to metal M;
m+n is the maximum number of ligands that may be attached to metal M.
5. The device of claim 4 , wherein the carbene based compound is selected from the group consisting of:
wherein c is 0, 1, or 2; and
wherein R 4 is selected from H, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group.
6. The device of claim 3 , wherein the carbene based compound is Ir(pmp) 3 .
7. The device of claim 4 , wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Ti, Pb, Bi, In, Sn, Sb, Te, Al, Ga, Au, and Ag.
8. The device of claim 7 , wherein M is Ir.
9. The device of claim 8 , wherein m is 3 and n is 0.
10. The device of claim 3 , wherein the carbene ligand has the structure;
wherein ring D is an aromatic cyclic, heterocyclic, fused cyclic, or fused heterocyclic ring, wherein ring D can be optionally substituted with one or more substituents R 2 ;
R 1 and R 2 are independently selected from H, alkyl, alkenyl, alkynyl, aralkyl, CN, CF 3 , CO 2 R′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, SO 3 R′, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; R 3 is H, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group; and additionally or alternatively, two R groups on the same or adjacent ring, together may form independently a 5 or 6-member cyclic group, which is a cycloalkyl, cycloheteroalkyl, aryl, or heteroaryl; and wherein said cyclic group may be substituted by one or more substituents J;
each substituent J is independently selected from the group consisting of R′, CN, CF 3 , C(O)OR′, C(O)R′, C(O)NR′ 2 , NR′ 2 , NO 2 , OR′, SR′, SO 2 , SOR′, or SO 3 R′, and additionally, or alternatively, two J groups on adjacent ring atoms may form a fused 5- or 6-membered aromatic group;
each R′ is independently selected from halo, H, alkyl, alkenyl, alkynyl, heteroalkyl, aralkyl, aryl, and heteroaryl;
Z 1 is selected from a bond, O, S, or NR′;
A 1 and A 2 are independently selected from C, N, or P; and
a is 0, 1, 2, 3, or 4;b is 0, 1, or 2.
11. The device of claim 10 , wherein the carbene ligand is selected from:
wherein c is 0, 1, or 2.
12. The device of claim 10 , wherein the carbene ligand is selected from the group consisting of:
wherein c is 0, 1, or 2; and
wherein R 4 is selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group.
13. The device of claim 4 , wherein each of R 1 is H or an alkyl having 1-15 carbons and each of R 2 is H or an alkyl having 1-15 carbons.
14. The device of claim 13 , wherein M is Ir or Pt.
15. The device of claim 4 , wherein D is a 5-membered aromatic heterocyclic ring.
16. The device of claim 15 , wherein D is selected from the group consisting of
wherein R4 is selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, or a heterocyclic group.
17. The device of claim 4 , wherein D is a 6-membered aromatic heterocyclic ring.
18. The device of claim 17 , wherein D is
19. The device of claim 4 , wherein D-Z 1 is
20. The device of claim 1 , further comprising a hole blocking layer disposed between the organic emissive layer and the cathode;
wherein the organic emissive layer and the electron blocking layer forming an emissive layer/electron blocking layer interface and the organic emissive layer and the hole blocking layer forming an emissive layer/hole blocking layer interface; and
wherein the organic phosphorescent emissive dopant material is present in the organic emissive layer with a graded doping concentration wherein the doping concentration is linearly graded from highest concentration at the emissive layer/electron blocking layer interface, to lowest concentration at the emissive layer/hole blocking layer interface.
21. A device comprising one or more organic light emitting devices of claim 1 .