Tetradentate and octahedral metal complexes containing naphthyridinocarbazole and its analogues

• US 9,879,039 B2
• Filed: 05/31/2016
• Issued: 01/30/2018
• Est. Priority Date: 06/03/2015
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian, Li, Guijie
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US15/168,942
• Publication Number:
  US 20160359125A1
• Time in Patent Office: 609 Days
• Field of Search: 546 10, 313504
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/006 Palladium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• 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 2101/27 Combination of fluorescent and phosphorescent emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/40 Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Tetradentate and octahedral metal complexes suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.

Claims

1. A complex of Formula AIV:

2. The complex of claim 1, wherein the complex has a neutral charge.

4. The complex of claim 1, wherein each of

6. An emitter comprising the complex of claim 1, wherein the emitter is a delayed fluorescent and phosphorescent emitter.

7. An emitter comprising the complex of claim 1, wherein the emitter is a phosphorescent emitter.

8. An emitter comprising the complex of claim 1, wherein the emitter is a delayed fluorescent emitter.

9. The complex of claim 1, wherein polymeric comprises polyalkylene, polyester, or polyether.

10. The complex of claim 9, wherein polymeric comprises —

(CH₂O)_n—

CH₃, —

(CH₂CH₂O)_n—

CH₃, —

[CH₂CH(CH₃)]_n—

CH₃, —

[CH₂CH(COOCH₃)]_n—

CH₃, —

[CH₂CH(COOCH₂CH₃)]_n—

CH₃, or —

[CH₂CH(COO^tBu)]_n—

CH₃, where n is an integer.

11. A device comprising a complex of claim 1.

12. The complex of claim 1, wherein each of A¹, A², A³, and A⁴ is independently a single bond, CR¹R², C═

O, SiR¹R², NR³, O, S, S═

O, or SO₂.

13. The complex of claim 1, wherein each of A¹, A², A³, and A⁴ is independently a single bond, CR¹R², NR³, or O.

14. The complex of claim 1, wherein each of A¹, A², A³, and A⁴ is independently a single bond or CR¹R².

15. The complex of claim 1, wherein A⁵ is O, NR³, or CR¹R².

16. The complex of claim 1, wherein A⁵ is O.

17. The complex of claim 1, wherein each R¹, R² and R³ is independently hydrogen, deuterium, halogen, hydroxyl;

substituted or unsubstituted;

aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, or haloalkyl.

18. The complex of claim 1, wherein each R¹, R² and R³ is independently hydrogen;

substituted or unsubstituted;

aryl, alkyl, alkenyl, or alkynyl.

19. The complex of claim 1, wherein each of R^a, R^b, R^c, and R^d is independently present or absent, and if present each of R^a, R^b, R^c, and R^d is independently a mono-, di-, or tri-substitution as valency permits, and each of R^a, R^b, R^c, and R^d is independently hydrogen, halogen, hydroxyl;

substituted or unsubstituted;

aryl, heteroaryl, alkyl, alkenyl, or alkynyl, and

each of R^x and R^y is independently hydrogen, halogen, hydroxyl;

substituted or unsubstituted;

aryl, heteroaryl, alkyl, alkenyl, or alkynyl.

20. The complex of claim 1, wherein the complex is

3. A complex represented by one of the chemical structures:

5. An emitter comprising the complex of claim 3.