Rhodium and iridium complexes

• US 20060127696A1
• Filed: 08/14/2003
• Published: 06/15/2006
• Est. Priority Date: 08/24/2002
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck OLED Materials GmbH (Avecia Limited)
• Inventors: Spreitzer, Hubert, Bach, Ingrid, Stossel, Philipp
• Granted Patent: US 7,883,785 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0073 Rhodium compounds
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/007 Squaraine dyes
• CPC Class Codes: C09B 57/10 Metal complexes of organic compounds not being dyes in uncomplexed form
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

The present invention describes novel organometallic compounds which are phosphorescent emitters. Such compounds can be used as active components (=functional materials) in a variety of different applications which can in the widest sense be considered part of the electronics industry. The compounds of the invention are described by the formulae (I), (Ia), (II) and (IIa).

Claims

1. A compound of the formula (I) or (II),

3. The compound as claimed in claim 1 in which the symbol Y is O or S.

4. The compound as claimed in claim 1, characterized in that Y is R—

C═

C—

R or R—

C═

N—

.

5. The compound as claimed in claim 1, characterized in that b=0.

6. The compound as claimed in claim 1, characterized in that Ar is an aryl group.

7. The compound as claimed in claim 1, characterized in that Ar is a heteroaryl group.

8. The compound as claimed in claim 6, characterized in that the radical Ar is benzene, toluene, xylene, fluorobenzene, difluorobenzene, diphenyl, 1,2- or 1,3- or 1,4-terphenylene, tetraphenylene, naphthalene, fluorene, phenanthrene, anthracene, 1,3,5-triphenylbenzene, pyrene, perylene, chrysene, triptycene, [2.2]paracyclophane, pyridine, pyridazine, 4,5-benzo-pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, pyrrole, indole, 1,2,5- or 1,3,4-oxadiazole, 2,2′

- or 4,4′

-diazabiphenyl, quinoline, carbazole, 5,10H-dihydrophenazine, 10H-phenoxazine, phenothiazine, xanthene, 9-acridine, furan, benzofuran, thiophene or benzothiophene.

9. The compound as claimed in claim 6, characterized in that Ar is carbazole, N-alkylcarbazole, N-alkylphenoxazines, phenothiazine or xanthene or a mixture thereof.

10. The compound as claimed in claim 6, characterized in that Ar is phenyl, 1- or 2-naphthyl, 1-, 2- or 9-anthracenyl.

11. The compound as claimed in claim 1, characterized in that Q is F, Cl, Br, CN, NO₂ SiR₃ or a straight-chain or branched or cyclic alkyl or alkoxy group which has from 1 to 6 carbon atoms and in which one or more adjacent CH₂ groups optionally replaced by —

CF₂—

.

12. The compound as claimed in claim 1, characterized in that M=Ir.

13. The compound as claimed in claim 1, characterized in that c is greater than or equal to 1.

14. A process for preparing compounds as claimed in claim 1, by reacting compounds of the formula (III) or (IV),

16. A mixture of one or more compounds of the formula (I) and/or the formula (II) as claimed in claim 1, with an unconjugated, partially conjugated or conjugated polymer.

17. The mixture as claimed in claim 16, characterized in that the polymer is selected from the group consisting of polyfluorenes, polyspirobifluorenes, poly-para-phenylenes, polycarbazoles, polyvinylcarbazoles, polythiophenes and copolymers comprising a plurality of the units mentioned here.

18. The mixture as claimed in claim 16, characterized in that the polymer is soluble in organic solvents.

22. An electronic component comprising a compound as claimed in claim 1.

23. An organic electroluminescence and/or phosphorescence device which comprises the compound as claimed in claim 1.

24. An emission layer which comprises the compound as claimed in claim 1.

25. A solar cell or photovoltaic device which comprises the compound as claimed in claim 1.

26. The solar cell or photovoltaic device as claimed in claim 25, wherein the solar cell or photovoltaic device is an organic photodetector, an organic solar cell, in an organic integrated circuits, in an organic field effect transistor, in an organic thin film transistor or in an organic solid-state laser.

2. A compound of the formula (Ia) or (IIa),

15. The compound as claimed in claim, characterized in that its purity (determined by means of 1H-NMR and/or HPLC) is more than 99%.

19-21. -21. (canceled)