# US 2020/0403166 A1 · Organic electroluminescent materials and devices

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- Number: US 2020/0403166 A1
- Document ID: US20200403166A1
- Status: Published application
- Kind: A1
- Application number: 17/012,997
- Filed: 2020-09-04
- Published: 2020-12-24
- Earliest claimed: 2015-06-04
- Assignees: University of Southern California
- Applicants: University of Southern California
- Inventors: Mark E. THOMPSON; Matthew J. JUROW; Peter I. DJUROVICH; Tobias D. SCHMIDT
- Web page: https://patentgrep.com/patent/US20200403166A1

## CPC

- H10K 85/342: {comprising iridium}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/30: Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### 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(LA)2(LB);
wherein LA and LB are bidentate, monoanionic ligands;
wherein each of the compounds has a structure of
wherein
represents ligand LA and
represents ligand LB;
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 C2 symmetry axis and a transition dipole moment vector (TDV);
wherein the ligand LB is symmetric with respect to the C2 symmetry axis;
wherein the Z atoms are trans to each other and the C2 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, CR2, or SiR2;
wherein R is H, alkyl, or aryl; and
wherein the heteroleptic compounds in the film are oriented with their C2 symmetry axis substantially perpendicular to the substrate.

### Claim 2 (depends on 1)

The first organic light emitting device of claim 1, wherein the ligand LA is
wherein Y is CR2, or SiR2; and
wherein A is H, CN, NO2, or C(O)R.

### Claim 3 (depends on 1)

The first organic light emitting device of claim 1, wherein the ligand LA in the formula M(LA)2(LB) is selected from the group consisting of:
wherein Z1 and Z2 are independently H, alkyl, aryl, alkynyl, C(O)R, or CO2R;
wherein R is H, alkyl, or aryl; and
wherein Z3 is H, alkyl, alkynyl, CN, C(O)R, CO2R, or NO2;
wherein A is O, S, NR, PR, CO, CR2, or SiR2; and
wherein R is H, alkyl, or aryl.

### Claim 4

(canceled)

### Claim 5 (depends on 2)

The first organic light emitting device of claim 2, wherein LB is selected from the group consisting of:

### Claim 6 (depends on 2)

The first organic light emitting device of claim 2, wherein LB is selected from the group consisting of:
wherein Z is H, alkyl, aryl, alkynyl, CN, C(O)R, CO2R, or NO2; and
wherein R is H, alkyl, or aryl.

### Claim 7 (depends on 1)

The first organic light emitting device of claim 1, wherein the ligand LB is one of the following anionic borate ligands:
wherein Z1 and Z2 are independently H, alkyl, aryl, alkynyl, C(O)R, or CO2R, and
wherein R is H, alkyl, or aryl.

### Claim 8 (depends on 1)

The first organic light emitting device of claim 1, wherein the ligand LA is one of the following anionic ligands:
wherein Z3 is H, alkyl, aryl, alkynyl, CN, C(O)R, CO2R, or NO2;
wherein A is O, S, NR, PR, CO, CR2, or SiR2; and
wherein R is H, alkyl, or aryl.

### Claim 9 (depends on 1)

The first organic light emitting device of claim 1, wherein the heteroleptic compound is
wherein A is H, CN, NO2, C(O)R, or CO2R;
X is O, NR, CR2, or SiR2; and
R is H, alkyl, or aryl.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

The first organic light emitting device of claim 1, wherein 0 is 0.1 or less.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

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 CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡C—CnH2n+1, Ar1, Ar1—Ar2, and CnH2n—Ar1, or the host has no substitutions;
wherein n is from 1 to 10; and
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 1)

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

### Claim 16 (depends on 1)

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.

### Claim 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(LA)3;
wherein the compound has a structure of
wherein
represents LA,
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 LA is a C2 symmetric bidentate monoanionic ligand and each ligand LA's coordination to M forms a L-M-L bond angle;
wherein each of the homoleptic compound is a C3 symmetric compound having a C3 symmetry axis and has a transition dipole moment; and
wherein the homoleptic compounds in the film are oriented with their C3 symmetry axis substantially perpendicular to the substrate and the transition dipole moment for the M(LA) fragment bisects the L-M-L bond angle.

### Claim 18 (depends on 17)

The first organic light emitting device of claim 17, wherein M is Ir.

### Claim 19 (depends on 17)

The first organic light emitting device of claim 17, wherein LA is selected from the group consisting of:
wherein X is halide, alkyl, aryl, or alkoxide;
wherein Y is O or NR;
wherein Z is H, alkyl, aryl, CN, or NO2;
wherein A is O, S, NR, PR, CO, CR2, or SiR2; and
wherein R is H, alkyl, or aryl.

### Claim 20 (depends on 17)

The first organic light emitting device of claim 17, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

### Claim 21 (depends on 17)

The first organic light emitting device of claim 17, 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 CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡C—CnH2n+1, Ar1, Ar1—Ar2, and CnH2n—Ar1, or the host has no substitutions;
wherein n is from 1 to 10; and
wherein Ar1 and Ar2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

### Claim 22 (depends on 17)

The first organic light emitting device of claim 17, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

### Claim 23 (depends on 17)

The first organic light emitting device of claim 17, wherein the organic layer further comprises a host, wherein the host comprises a metal complex.

### Claim 24 (depends on 17)

The first organic light emitting device of claim 17, 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.