Method for synthesis of iriduim (III) complexes with sterically demanding ligands

• US 8,519,130 B2
• Filed: 03/07/2008
• Issued: 08/27/2013
• Est. Priority Date: 12/08/2006
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Alleyne, Bert
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US12/044,848
• Publication Number:
  US 20090124805A1
• Time in Patent Office: 1,999 Days
• Field of Search: 546/2, 546/6
• US Class Current: 546/2
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• 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: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Phosphorescent materials and devices with improved device manufacturing, fabrication, stability, efficiency, and/or color.

Claims

1. A process for making an Ir(L_a)(L_b)(L_c) complex, comprising:

reacting an intermediate having the formula (L_a)(L_b)IrX with L_c to produce an Ir(L_a)(L_b)(L_c) complex,

where L_a, L_b and L_c are, independently, bidentate cyclometallated ligands having the formula;

2. The process of claim 1, wherein L_a, L_b, and L_c are photoactive.

3. The process of claim 2, wherein R′

₆ is hydrogen, and R₃ is selected from the group consisting of alkyl, alkenyl, alkynyl, alkylaryl, CN, NO₂, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, and a heterocyclic group.

4. The process of claim 3, wherein the yield of Ir(L_a)(L_b)(L_c) is at least 50%.

5. The process of claim 3, wherein the yield of Ir(L_a)(L_b)(L_c) is at least 30%.

6. The process of claim 2, wherein R₃ is hydrogen, and R′

₆ is selected from the group consisting of alkyl, alkenyl, alkynyl, alkylaryl, CN, NO₂, halo, aryl, heteroaryl, substituted aryl, substituted heteroaryl, and a heterocyclic group.

7. The process of claim 5, wherein the yield of Ir(L_a)(L_b)(L_c) is at least 10%.

8. The process of claim 2, wherein L_a, L_b, and L_c are the same.

9. The process of claim 2, wherein R₆ is methyl, and R₃, R₄, R₅, R′

₃, R′

₄, R′

₅ and R′

₆ are hydrogen.

10. The process of claim 2, wherein R′

₃ is methyl, R′

₅ is methyl, R₄ is methyl and R₃, R₅, R₆, R′

₄, and R′

₆ are hydrogen.

11. The process of claim 2, wherein R′

₃ is methyl, R′

₅ is methyl, and R₃, R₄, R₅, R₆, R′

₄, and R′

₆ are hydrogen.