Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-12058929-B2
Application number	US-202017012997-A
Country	US
Kind code	B2
Filing date	Sep 4, 2020
Priority date	Jun 4, 2015
Publication date	Aug 6, 2024
Grant date	Aug 6, 2024

Abstract

Organic light emitting devices incorporating a film of metal complex emitters that are oriented with their transition dipole moment vectors oriented parallel to the device substrate enhances the outcoupling and eliminate the need for micro-lens arrays, gratings, or other physical extraneous outcoupling methods.

First claim

We claim:

1. A first organic light emitting device comprising:
a substrate;
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a film of heteroleptic compounds having a formula M(L A ) 2 (L B );
wherein L A and L B are bidentate, monoanionic ligands;
wherein each of the compounds has a structure of

 wherein

 represents ligand L A and

 represents ligand L B ;
wherein M is a metal selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein the compound has a C 2 symmetry axis and a transition dipole moment vector (TDV);
wherein the ligand L B is symmetric with respect to the C 2 symmetry axis;
wherein the Z atoms are trans to each other and the C 2 symmetry axis is perpendicular to the M-Z bonds and the TDV is coincident or nearly coincident with the M-Z bonds;
wherein the ligand L A is

wherein Y is CR 2 , or SiR 2 ;
wherein A is H, CN, NO 2 , or C(O)R;
wherein Z is C or N;
wherein X is O, NR, CR 2 , or SiR 2 ;
wherein R is H, alkyl, or aryl; and
wherein the heteroleptic compounds in the film are oriented with their C 2 symmetry axis substantially perpendicular to the substrate.

2. The first organic light emitting device of claim 1 , wherein L B is selected from the group consisting of:

3. The first organic light emitting device of claim 1 , wherein L B is selected from the group consisting of:

wherein Z is H, alkyl, aryl, alkynyl, CN, C(O)R, CO 2 R, or NO 2 , and
wherein R is H, alkyl, or aryl.

4. The first organic light emitting device of claim 1 , wherein the ligand L B is one of the following anionic borate ligands:

wherein Z 1 and Z 2 are independently H, alkyl, aryl, alkynyl, C(O)R, or CO 2 R, and wherein R is H, alkyl, or aryl.

5. The first organic light emitting device of claim 1 , wherein the heteroleptic compound is

6. The first organic light emitting device of claim 1 , wherein M is Ir.

7. The first organic light emitting device of claim 1 , wherein θ is 0.1 or less.

8. The first organic light emitting device of claim 1 , wherein the organic layer is an emissive layer and the compound is an emissive dopant.

9. The first organic light emitting device of claim 1 , wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr, N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C═C—C n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and C n H 2n —Ar 1 , or the host has no substitutions;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

10. The first organic light emitting device of claim 1 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

11. The first organic light emitting device of claim 1 , wherein the organic layer further comprises a host, wherein the host comprises a metal complex.

12. The first organic light emitting device of claim 1 , wherein the first organic light emitting device is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

13. The first organic light emitting device of claim 1 , wherein Y is CR 2 .

14. The first organic light emitting device of claim 13 , wherein each R is independently alkyl or aryl.

15. The first organic light emitting device of claim 1 , wherein Y is SiR 2 .

16. The first organic light emitting device of claim 15 , wherein each R is independently alkyl or aryl.

17. The first organic light emitting device of claim 1 , wherein Z is C.

18. The first organic light emitting device of claim 1 , wherein Z is N.

19. The first organic light emitting device of claim 1 , wherein X is O.

20. The first organic light emitting device of claim 1 , wherein X is NR.

21. The first organic light emitting device of claim 1 , wherein X is CR 2 .

22. The first organic light emitting device of claim 1 , wherein X is SiR 2 .

Assignees

• Univ Southern California
• Universal Display Corp

Inventors

• Thompson Mark E
• Jurow Matthew J
• Djurovich Peter I
• Schmidt Tobias D

Classifications

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title