IP Library Granted Patent US 7,579,090
Granted Patent B2
US 7,579,090 · App. 11/016,134 · Granted Aug 25, 2009

Organic element for electroluminescent devices

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Quick Facts
Patent No.
US 7,579,090
App. No.
11/016,134
Granted
Aug 25, 2009
Kind
B2
Abstract

An OLED device contains a layer comprising a hole transporting compound, a certain type of oxinoid compound, and a light emitting phosphorescent compound.

Claims (54)

1. An organic light emitting device containing a cathode, an anode, and having located there-between a light emitting layer comprising:

A) co-hosts including

a) a hole transporting compound, and

b) an oxinoid compound, wherein the oxinoid is an aluminum bis-(2-substituted)oxinoid compound bearing a third ligand linked to aluminum through an oxy moiety comprising an oxygen atom linked to an aromatic ring bearing at least one substituent at an ortho position; and

B) a red or orange light emitting phosphorescent compound wherein the phosphorescent compound has a triplet energy smaller than that of the co-hosts.

2. The device of claim 1 wherein there are substituents at ortho and meta positions on the oxy moiety that join to form a fused ring.

3. The device of claim 1 wherein the oxy moiety includes two substituents selected from the ortho and meta positions, and a fused ring originating from substituents at the ortho and meta positions.

4. The device of claim 1 wherein the oxy moiety includes two ortho substituents.

5. An electroluminescent device according to claim 1 wherein the oxinoid is selected from the group consisting of the following:

6. An electroluminescent device according to claim 1 wherein the hole transporting compound includes a triarylamine with a triplet energy greater than that of the dopant.

7. An electroluminescent device according to claim 1 wherein the hole transporting compound includes one selected from benzidine based triarylamines.

8. An electroluminescent device according to claim 1 wherein the hole transporting compound is selected from 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl; 4,4′-bis[N-(3-methylphenyl)-N-phenylamino]biphenyl; and 4,4′-Bis[N-(1-naphthyl)-N-(2-naphthyl)amino]biphenyl.

9. An electroluminescent device according to claim 1 wherein the hole transporting compound includes an azole.

10. An electroluminescent device according to claim 1 wherein the hole transporting compound is an azole selected from 4,4′-N,N′-dicarbazole-biphenyl; 4,4′-bis(9-carbazolyl)-2,2′-dimethylbiphenyl; and 4,4′,4″-tris(carbazol-9-yl)triphcnylamine.

11. The organic light emitting device of claim 1 wherein the oxinoid compound comprises a bis-oxinoid moiety and an oxy moiety and is represented by formula (1):

wherein:

R 2 represents an electron donating group,

R 3 and R 4 each independently represent hydrogen or an electron donating group,

R 5 , R 6, and R 7 each independently represent hydrogen or an electron accepting group, in the oxymoiety, R 10 represents hydrogen or a substituent group,

at least one of R 8 and R 12 represents a substituent group, and

R 9 and R 11 represent hydrogen or a substituent group, provided that two of R 8 -R 12 may join to form a ring.

12. The organic light emitting device of claim 11 with the proviso that R 9 and R 10 or R 11 , may join to form a fused ring provided only that at least one of the remaining R 8 , R 9 , R 11 , and R 12 represents a substituent group.

13. An electroluminescent device according to claim 11 wherein at least one of R 8 -R 12 is an alkyl or aryl group.

14. An electroluminescent device according to claim 11 wherein the oxinoid group is derived from one of the following:

15. An electroluminescent device according to claim 11 wherein the oxinoid is derived from a 2-methyl-8-hydroxyquinoline.

16. An electroluminescent device according to claim 11 wherein R 2 is an electron donating group selected from those having the formulas —R′, —OR′, and —NR′(R″) where R′ is a hydrocarbon containing up to 6 carbon atoms and R″ is hydrogen or R′ .

17. An electroluminescent device according to claim 15 wherein R 2 is an electron donating group selected from methyl, ethyl, phenyl, methoxy, ethoxy, phenoxy, —N(CH 3 ) 2 , —N(CH 2 CH 3 ) 2 , —NHCH 3 , —N(C 6 H 5 ) 2 , —N(CH 3 )(C 6 H 5 ), and —NHC 6 H 5 groups.

18. An electroluminescent device according to claim 11 wherein at least one of R 5 , R 6 , and R 7 is an electron accepting group.

19. An electroluminescent device according to claim 11 wherein at least one of R 5 , R 6 , and R 7 is chosen from cyano, α-haloalkyl, α-haloalkoxy, amido, sulfonyl, carbonyl, carbonyloxy and oxycarbonyl groups.

20. An electroluminescent device according to claim 11 wherein at least one of R 5 , R 6 , and R 7 is chosen from include —CN, —F, —CF 3 , —OCF 3 , —CONHC 6 H 5 , —SO 2 C 6 H 5 , —COC 6 H 5 , —CO 2 C 6 H 5 , and —OCOC 6 H 5 groups.

21. An electroluminescent device according to claim 11 wherein the oxy moiety is derived from one of the following:

22. An electroluminescent device according to claim 11 wherein the oxy moiety is derived from the following

23. An electroluminescent device according to claim 1 wherein the light-emitting phosphorescent component is an organometallic complex.

24. The device of claim 1 wherein the phosphorescent emitting material is an organometallic compound comprising a 3rd-row transition metal.

25. The device of claim 24 wherein the metal is iridium or platinum.

26. The device of claim 24 wherein the organometallic complex includes a ligand that can be coordinated to a metal through an sp 2 carbon and a heteroatom.

27. The device of claim 26 wherein the ligand is a substituted or unsubstituted phenylpyridine.

28. The device of claim 24 wherein the organometallic compound is chosen from tris(1-phenylisoquinolinato-N,C 2′ )Iridium(III) ), bis(1-phenylisoquinolinato-N,C 2′ )iridium(III)(acetylacetonate), and platinum octaethylporphyrin.

29. The device of claim 6 wherein the triarylamine is present at a weight percent greater than 10 percent of the components in the LEL.

30. An electroluminescent device according to claim 1 , wherein the light-emitting layer is adjacent to a layer comprising a hole blocking material.

31. The device of claim 1 wherein the phosphorescent material compound is present in an amount of up to 15±5 wt % based on the co-host materials.

32. The device of claim 1 wherein the light-emitting material is part of a polymer.

33. The device of claim 1 which emits white light.

34. A display comprising the OLED device of claim 1 .

35. An area lighting device comprising the OLED device of claim 1 .

36. A process for emitting light by applying a potential across the device of claim 1 .

37. An electroluminescent device according to claim 1 wherein the light emitting phosphorescent compound is a tris-C,N-cyclometallated Iridium(III) complex.

38. An electroluminescent device according to claim 37 wherein the light emitting phosphorescent compound is a tris-C,N-cyclometallated Iridium(III) complex having one C,N-cyclometallating ligand different from the other two.

39. An electroluminescent device according to claim 1 wherein the light emitting phosphorescent compound is selected from the group consisting of bis(1-phenylisoquinolinato-N,C 2′ )(2-phenylpyridinato-N,C 2′ )Iridium(III), bis(2-phenylpyridinato-N,C 2′ )(1-phenylisoquinolinato-N,C 2′ )Iridium(III), bis(1-phenylisoquinolinato-N,C 2′l )( 2-phenyl-5-methyl-pyridinato-N,C 2′ )Iridium(III), bis(1-phenylisoquinolinato-N,C 2′ )(2-phenyl-4-methyl-pyridinato-N,C 2′ )Iridium(III), and bis(1-phenylisoquinolinato-N,C 2′ )(2-phenyl-3-methyl-pyridinato-N,C 2′ )Iridium(III).

40. An electroluminescent device according to claim 1 , wherein the oxy moiety is derived from

41. An electroluminescent device according to claim 40 , wherein the hole transporting compound includes NPB.

42. An electroluminescent device according to claim 40 , wherein the phosphorescent compound is

43. An electroluminescent device according to claim 41 , wherein the phosphorescent compound is

44. An electroluminescent device according to claim 40 , wherein the phosphorescent compound is non-polymeric.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2010
From: EASTMAN KODAK COMPANY
To: GLOBAL OLED TECHNOLOGY LLC
Reel/Frame 023998/0368 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2005
From: BROWN, CHRISTOPHER T.; DEATON, JOSEPH C.; PLACE, DAVID W.; KONDAKOVA, MARINA E.; HUO, SHOUQUAN
To: EASTMAN KODAK COMPANY
Reel/Frame 016228/0720 →