Organic electroluminescent materials and devices

• US 9,590,195 B2
• Filed: 02/28/2014
• Issued: 03/07/2017
• Est. Priority Date: 02/28/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Szigethy, Geza, Brooks, Jason
• Primary Examiner(s): Yamnitzky, Marie R.
• Application Number:
  US14/194,311
• Publication Number:
  US 20150249223A1
• Time in Patent Office: 1,103 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A compound including a Ligand L of Formula I:

as well as, a first device and a formulation containing the same, are disclosed. In the compound including the Ligand L of Formula I:

• • X is selected from the group consisting of S, Se, SiRR′ and GeRR′;
  • R¹, R², R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
  • any adjacent substitutions or substituents of R¹, R², R, and R′ are optionally linked together to form a ring;
  • the Ligand L is coordinated to a metal M having an atomic number of 40 or greater; and
  • the Ligand L is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.

Claims

1. A compound comprising a Ligand L of Formula I:

2. The compound of claim 1, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.

3. The compound of claim 1, wherein M is Ir.

4. The compound of claim 1, wherein the compound is homoleptic having formula of IrL₃.

5. The compound of claim 4, wherein said compound is a facial isomer.

6. The compound of claim 4, wherein said compound is a meridional isomer.

7. The compound of claim 1, wherein the compound is heteroleptic.

8. The compound of claim 1, wherein R¹, and R² are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.

9. The compound of claim 1, wherein at least one of R¹ and R² is a moiety selected from the group consisting of phenyl, toluene, biphenyl and tetraphenyl.

10. The compound of claim 1, wherein X is GeRR′

, and R and R′

are each independently selected from the group consisting of alkyl, aryl, heteroaryl, and combinations thereof.

11. The compound of claim 1, wherein R¹ is mono-substitution on the ortho position to N, and R¹ is selected from the group consisting of halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

20. The compound of claim 1, wherein the compound is selected from the group consisting of:

12. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a Ligand L of Formula I;

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

14. The first device of claim 12, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

15. The first device of claim 12, wherein the organic layer further comprises a host material.

16. The first device of claim 15, wherein the host material comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host material is an unfused substituent independently selected from the group consisting of C_nH_2n+1, OAr₁, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_nH_2n+1, C≡

C—

C_nH_2n+1, Ar₁, Ar₁—

Ar₂, and C_nH_2n—

Ar₁;

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.

17. The first device of claim 15, wherein the host material comprises at least one chemical group selected from the group consisting of carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

18. The first device of claim 15, wherein the host material is selected from the group consisting of:

19. A formulation comprising a compound comprising a Ligand L of Formula I: