Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-2016359123-A1
Application number	US-201615174409-A
Country	US
Kind code	A1
Filing date	Jun 6, 2016
Priority date	Jun 4, 2015
Publication date	Dec 8, 2016
Grant date	—

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

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 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 the ligand L A is

wherein Y is CR 2 , or SiR 2 ; and
wherein A is H, CN, NO 2 , or C(O)R.

3 . The first organic light emitting device of claim 1 , wherein the ligand L A in the formula

wherein HET refers to a heterocyclic ring;
wherein Z 4 is H, alkyl, aryl, alkynyl, CN, C(O)R, CO 2 R, or NO 2 ;
wherein A is O, S, NR, PR, CO, CR 2 , or SiR 2 ;
wherein R is H, alkyl, or aryl; and
wherein the triplet energy of the ligand L A is ≧3.0 eV.

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

M(L A ) 2 (L B ) is selected from the group consisting of:

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; and

wherein Z 3 is H, alkyl, alkynyl, CN, C(O)R, CO 2 R, or NO 2 ;
wherein A is O, S, NR, PR, CO, CR 2 , or SiR 2 ; and
wherein R is H, alkyl, or aryl.

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

6 . The first organic light emitting device of claim 2 , 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.

7 . 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.

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

wherein Z 3 is H, alkyl, aryl, alkynyl, CN, C(O)R, CO 2 R, or NO 2 ;
wherein A is O, S, NR, PR, CO, CR 2 , or SiR 2 ; and
wherein R is H, alkyl, or aryl.

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

wherein A is H, CN, NO 2 , C(O)R, or CO 2 R;
X is O, NR, CR 2 , or SiR 2 ; and
R is H, alkyl, or aryl.

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

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

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

13 . 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 1 , 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.

14 . 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.

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

16 . 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.

17 . 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 homoleptic compounds having a formula M(L A ) 3 ; wherein the compound has a structure of

wherein

 represents L A ,
wherein M is a metal selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;
wherein L is C or N atom;
wherein L A is a C 2 symmetric bidentate m

Assignees

• Univ Southern California

Inventors

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

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/185

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

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F15/004

  without a metal-carbon linkage · CPC title