Mixed ligand 8-quinolinolato aluminum chelate luminophors

• US 5,141,671 A
• Filed: 08/01/1991
• Issued: 08/25/1992
• Est. Priority Date: 08/01/1991
• Status: Expired due to Term

• Current Assignee: Global OLED Technology LLC (LG Display Co., Ltd.)
• Original Assignee: Eastman Kodak Company
• Inventors: Lovecchio, Frank V., VanSlyke, Steven A., Bryan, Philip S.
• Primary Examiner(s): Willis, Jr., Prince
• Assistant Examiner(s): Steinberg, Thomas
• Application Number:
  US07/738,751
• Time in Patent Office: 390 Days
• Field of Search: 546/7, 313/504, 252/301.16, 252/301.26
• US Class Current: 252/301.16
• CPC Class Codes: C07F 5/069 without C-aluminium linkages
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/321 Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]

Abstract

A blue-emitting luminescent composition is disclosed comprised of an aluminum chelate containing a phenolato ligand and two R^s -8-quinolinolato ligands, where R^s substituents are chosen to block the attachment of more than two substituted 8-quinolinolato ligands to the aluminum atom. The presence of the phenolato ligand shifts emission to the blue region of the spectrum. Emission can be shifted to even shorter blue wavelengths by the incorporation of a pentacarbocyclic aromatic fluorescent dye.

Claims

1. A blue emitting luminescent composition comprised of an aluminum chelate of the formula:

space="preserve" listing-type="equation">(R.sup.S --Q).sub.2 --Al--O--L

where

Q in each occurrence represents a substituted 8-quinolinolato ligand,

R^S represents an 8-quinolinolato ring substituent chosen to block sterically the attachment of more than two substituted 8-quinolinolato ligands to the aluminum atom, and

L is a phenyl or aromatic fused-ring moiety which can be substituted with hydrocarbon groups such that L has from 6 to 24 carbon atoms.

2. A blue emitting luminescent composition according to claim 1 further characterized in that R^S is a 2-position substituent of the 8-quinolinolato ring

3. A blue emitting luminescent composition according to claim 2 further characterized in that R^S is an electron donating substituent.

4. A blue emitting luminescent composition according to claim 3 further characterized in that R^S is chosen from the group consisting of amino, oxy and hydrocarbon groups containing up to 10 carbon atoms.

5. A blue emitting luminescent composition according to claim 4 further characterized in that R^S is a hydrocarbon containing from 1 to 6 carbon atoms.

6. A blue emitting luminescent composition according to claim 1 further characterized in that the 8-quinololato ring nucleus includes a 4-position ring substituent that is electron donating.

7. A blue emitting luminescent composition according to claim 6 further characterized in that the 4-position ring substituent is chosen from among amino, oxy and hydrocarbon groups containing up to 10 carbon atoms.

8. A blue emitting luminescent composition according to claim 1 further characterized in that the 8-quinolinolato ring nucleus includes in at least one of its 5, 6 and 7 ring positions a substituent that is electron accepting.

9. A blue emitting luminescent composition according to claim 8 further characterized in that each of the 5, 6 and 7 ring position electron accepting substituents is chosen from among electron accepting cyano, halogen, and α

-haloalkyl, α

-haloalkoxy, amido, sulfonyl, carbonyl, carbonyloxy and oxycarbonyl substituents containing up to 10 carbon atoms.

10. A blue emitting luminescent composition according to claim 1 further characterized in that the aluminum chelate satisfies the formula:

##STR27## where R² represents an electron donating substituent,

R³ and R⁴ each independently represent hydrogen or an electron donating substituent,

R⁵, R⁶ and R⁷ each independently represent hydrogen or an electron accepting substituent, and

L is a phenyl or aromatic fused-ring moiety which can be substituted with hydrocarbon groups such that L has from 7 to 18 carbon atoms.

11. A blue emitting luminescent composition according to claim 10 further characterized in that the electron donating substituents are independently chosen from the group consisting of --R'"'"', --OR'"'"' and --N(R")R'"'"', where R'"'"' is a hydrocarbon containing up to 6 carbon atoms and R" is hydrogen or R'"'"' and the electron accepting substituents are each independently chosen from among electron accepting cyano, halogen, and α

-haloalkyl, α

-haloalkoxy, amido, sulfonyl, carbonyl, carbonyloxy and oxycarbonyl substituents containing up to 6 carbon atoms.

12. A blue emitting luminescent composition according to claim 1 further characterized in that the hydrocarbon includes at least one aliphatic substituent of the phenyl moiety.

13. A blue emitting luminescent composition according to claim 12 further characterized in that the aliphatic substituent contains from 1 to 10 carbon atoms.

14. A blue emitting luminescent composition according to claim 13 further characterized in that the hydrocarbon includes at least one alkyl substituent of the phenyl moiety.

15. A blue emitting luminescent composition according to claim 13 further characterized in that the hydrocarbon includes at least two alkyl substituents of the phenyl moiety.

16. A blue emitting luminescent composition according to claim 14 further characterized in that the aliphatic substituent contains from 1 to 3 carbon atoms.

17. A blue emitting luminescent composition An internal junction organic electroluminescent device according to claim 1 further characterized in that a benzo ring is fused with the phenyl moiety.

18. A blue emitting luminescent composition according to claim 1 further characterized in that the hydrocarbon includes at least one aromatic substituent of the phenyl moiety.

19. A blue emitting luminescent composition according to claim 18 further characterized in that the aromatic substituent is comprised of a phenyl ring.

20. A blue emitting luminescent composition according to claim 1 further characterized in that the aluminum chelate satisfies the formula:

##STR28## where Q in each occurrence represents a substituted 8-quinolinolato ring nucleus,

R² in each occurrence represents a 2-position electron donating substituent of the 8-quinolinolato ring nucleus, and

L¹, L², L³, L⁴ and L⁵ collectively contain 12 or fewer carbon atoms and each independently represent hydrogen or hydrocarbon groups of from 1 to 12 carbon atoms, with the proviso that L¹ and L² together or L² and L³ together can form a fused benzo ring.

21. A blue emitting luminescent composition according to claim 1 further characterized in that the luminescent layer additionally includes a fluorescent

22. A blue emitting luminescent composition according to claim 21 further characterized in that the fluorescent dye is chosen to provide a favored recombination site for holes and electrons and is blue emitting.

23. A blue emitting luminescent composition according to claim 22 further characterized in that the blue emitting fluorescent dye exhibits a shorter wavelength emission peak than the aluminum chelate.

24. A blue emitting luminescent composition according to claim 22 further characterized in that the blue emitting fluorescent dye contains a stabilizing aromatic chromophoric unit containing at least 5 fused carbocyclic aromatic rings.

25. A blue emitting luminescent composition according to claim 24 further characterized in that the chromophoric unit contains from 20 to 40 ring carbon atoms.

26. A blue emitting luminescent composition according to claim 25 further characterized in that the fluorescent dye chromophoric unit is chosen from among those containing a perylene, benzopyrene, benzochrysene, benzonaphthacene, picene, pentaphene, pentacene, hexacene or anthanthrene nucleus.

27. A blue emitting luminescent composition according to claim 24 further characterized in that the fluorescent dye is present in a concentration ranging from 0.05 to 5 mole percent.

28. A blue emitting luminescent composition according to claim 27 further characterized in that the fluorescent dye is present in a concentration ranging from 0.2 to 3 mole percent.

29. A blue emitting luminescent composition according to claim 27 further characterized in that the fluorescent dye is present in a concentration ranging from 0.5 to 2 mole percent.

30. A blue emitting luminescent composition comprised of an aluminum chelate chosen from the group consisting of

bis(2-methyl-8-quinolinato)(phenolato)-aluminum(III);

bis(2-methyl-8-quinolinato)(ortho-cresolato)-aluminumn(III);

bis(2-methyl-8-quinolinato)(meta-cresolato)-aluminum(III);

bis(2-methyl-8-quinolinato)(para-cresolato)-aluminum(III);

bis(2-methyl-8-quinolinato)(ortho-phenylphenolato)-aluminum(III);

bis(2-methyl-8-quinolinato)(meta-phenylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(para-phenylphenolato)-aluminum(III);

bis(2-methyl-8-quinolinato)(2,3-dimethylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(2,6-dimethylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(3,4-dimethylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(3,5-di-tert.-butylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(2,6-diphenylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(2,4,6-tri-phenylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(2,3,6-tri-methylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(2,3,5,6-tetramethylphenolato)aluminum(III);

bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum(III);

bis(2-methyl-8-quinolinato)(2-naphtholato)aluminum(III);

bis(2,4-dimethyl-8-quinolinato)(ortho-phenylphenolato)aluminum(III);

bis(2,4-dimethyl-8-quinolinato)(para-phenylphenolato)aluminum(III);

bis(2,4-dimethyl-8-quinolinato)(meta-phenylphenolato)aluminum(III);

bis(2,4-dimethyl-8-quinolinato)(3,5-dimethylphenolato)aluminum(III); and

bis(2,4-dimethyl-8-quinolinato)(3,5-di-tert-butylphenolato)aluminum(III).