IP Library Granted Patent US 10,074,815
Granted Patent B2
US 10,074,815 · App. 15/086,795 · Granted Sep 11, 2018

Organic electroluminescent devices

Inventors: Stephen R. Forrest (Ann Arbor, MI); Jaesang Lee (Seoul, KR); Mark E. Thompson (Anaheim Hills, CA)
Assignees: THE REGENTS OF THE UNIVERSITY OF MICHIGAN; UNIVERSITY OF SOUTHERN CALIFORNIA
H01L51/0085C09K11/025C09K11/06H05B33/14H05B33/20C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/185H01L51/0058H01L51/0067H01L51/0072H01L51/5016H01L51/5096H01L2251/5346
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Quick Facts
Patent No.
US 10,074,815
App. No.
15/086,795
Granted
Sep 11, 2018
Kind
B2
Abstract

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.

Claims (51)

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 .

Assignments (3)
CONFIRMATORY LICENSE Recorded Aug 3, 2016
From: MICHIGAN, UNIVERSITY OF
To: ENERGY, UNITED STATES DEPARTMENT OF
Reel/Frame 039627/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2016
From: THOMPSON, MARK E.
To: UNIVERSITY OF SOUTHERN CALIFORNIA
Reel/Frame 038339/0241 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2016
From: FORREST, STEPHEN R.; LEE, JAESANG
To: THE REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 038251/0809 →
Continuity (2)
Provisional Application 62140746 · Mar 31, 2015
Related Publication 20160293864A1 · Oct 6, 2016