IP Library Granted Patent US 6,876,684
Granted Patent B2
US 6,876,684 · App. 10/269,652 · Granted Apr 5, 2005

Organic vertical cavity lasing device having organic active region

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,876,684
App. No.
10/269,652
Granted
Apr 5, 2005
Kind
B2
Abstract

An organic vertical cavity laser light producing device includes a bottom dielectric stack reflective to light over a predetermined range of wavelengths; an organic active region for producing laser light, and having an organic active region including emissive material; and a top dielectric stack spaced from the bottom dielectric stack and reflective to light over a predetermined range of wavelengths. Pump-beam light is transmitted and introduced into the organic active region through at least one of the dielectric stacks. The organic active region includes one or more periodic gain region(s) and organic spacer layers disposed on either side of the periodic gain region(s) and arranged so that the periodic gain region(s) is aligned with the antinodes of the device's standing wave electromagnetic field, and wherein the spacer layers are substantially transparent to the laser light.

Claims (62)

1. An organic vertical cavity laser light producing device, comprising:

a) a bottom dielectric stack reflective to light over a predetermined range of wavelengths;

b) an organic active layer for producing laser light, comprising an emissive material that has a host material;

c) a top dielectric stack spaced from the bottom dielectric stack and reflective to light over a predetermined range of wavelengths;

d) an external pump-beam light structure for producing light that is transmitted and introduced into the organic active region through at least one of the dielectric stacks wherein the absorption of the host material significantly overlaps the emission spectrum of the pump-beam light; and

e) the organic active layer is positioned between the bottom and top dielectric stacks and includes one or more periodic gain layers and organic spacer layers disposed on either side of the periodic gain layer(s) and arranged so that the periodic gain layer(s) is aligned with the antinodes of the device's standing wave electromagnetic field, and wherein the spacer layers are substantially transparent to the laser light.

2. The device of claim 1 wherein the emissive material includes a dopant.

3. The device of claim 2 wherein the absorption of the host material or the host material and the dopant is small at the laser emission wavelength of the device.

4. The device of claim 2 wherein the emission of the host material significantly overlaps the absorption of the dopant.

5. The device of claim 1 wherein the spacer layers have insignificant absorption at or above the emission of the pump-beam light.

6. The device of claim 1 wherein the spacer layers comprise a compound selected from the group consisting 1,2,3,4-tetraarylnaphthalene, mono-, 1,3-di-, 1,3,5-tri-, or 1,3,5,7-tetraaryladamantane, tetraarylmethane or triptycene compounds, which compounds may be substituted or unsubstituted, and combinations thereof.

7. The device of claim 1 wherein the spacer layers comprise a compound selected from the group consisting of 1,2,3,4-tetraphenylnaphthalene, 1,3,5-tri(3,5-dimethylphenyl)adamantane, 1,3,5,7-tetra(4-biphenyl)adamantane, 1,1-bis-(4-bis(4-methyl-phenyl)-amino-phenyl)-cyclohexane, tetra(4-biphenyl)methane, and 2-t-butyl-9,10-o-benzeno-9,10-dihydroanthracene, which compounds may be substituted or unsubstituted, and combinations thereof.

8. The device of claim 1 wherein the host material comprises a fluorescent aromatic compound.

9. The device of claim 1 wherein the host material includes a compound selected from the group consisting of derivatives of tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran, thiopyran, polymethine, pyrilium, thiapyrilium, napthyridine, fluoranthene, furan, indole, thiaphene, benzoxanthene, pyrene, peropyrene, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, fluorene, anthanthrene, bisanthrene, N,N,N′,N′-tetrasubstituted benzidene, N,N,N′,N′-tetrarylbenzidene, and carbostyryl compounds, which compounds may be substituted or unsubstituted, and combinations thereof.

10. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of a substituted aza-aromatic compound and an unsubstituted aza-aromatic compound.

11. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of acridine, quinoline, purine, phenazine, phenoxazine, and phenanthroline compound, which compound may be substituted or unsubstituted.

12. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of a substituted triarylamine compound and an unsubstituted triarylamine compound.

13. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of chelated oxinoid compound, a dicarbazole-biphenyl compound, and a anthracene compound, which compound may be substituted or unsubstituted.

14. The device of claim 1 wherein the host material comprises a compound containing at least three phenylene moieties.

15. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of a substituted chelated oxinoid compound and an unsubstituted chelated oxinoid compound.

16. The device of claim 1 wherein the host material comprise compound selected from the group consisting of a substituted dicarbazole-biphenyl compound and an unsubstituted dicarbazole-biphenyl compound.

17. The device of claim 16 wherein the host material comprises 4,4′-N,N′-dicarbazole-1,1′-biphenyl (CBP).

18. The device of claim 1 wherein the host material comprises a compound selected form the group of a substituted anthracene compound and unsubstituted anthracene compound.

19. The device of claim 18 wherein the host material comprises 9,10-di-(2-naphthyl)anthracene.

20. The device of claim 18 wherein the host material comprises 2-t-butyl-9,10-di-(2-naphthyl)anthracene.

21. The device of claim 18 wherein the host material comprises 9,10-bis-(4-(2,2′-diphenylethenyl)phenyl)anthracene.

22. The device of claim 1 wherein the host material comprises a compound selected from the group consisting of a substituted benzoxazole compound, an unsubstituted benzoxazole compound, a substituted benzthiazole compound, an unsubstituted benzthiazole compound, a substituted oxazole compound, an unsubstituted oxazole compound, a substituted triazole compound, an unsubstituted triazole compound, a substituted oxadiazole compound, an unsubstituted oxadiazole compound, a substituted benzimidazole compound, and an unsubstituted benzimidazole compound.

23. The device of claim 1 wherein the host material comprises a compound of the formula:

X—CH═CH—Y—CH═CH-Z

where X and Z are independently selected from the group consisting of a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic complex ring group, and an unsubstituted aromatic complex ring group, said aromatic complex ring group having one nitrogen atom, and Y is selected from the group consisting of a divalent aromatic group and a divalent aromatic complex ring group having one nitrogen atom.

24. The device of claim 1 wherein the host material comprises a compound of the formula:

X—(CH═CH) n -Z

where X and Z are independently selected from the group consisting of a substituted aromatic group and an unsubstituted aromatic group, a substituted aromatic complex ring group, and an unsubstituted aromatic complex ring group, said aromatic complex ring group having one nitrogen atom, and n equals 1, 2, or 3.

25. The device of claim 2 wherein the dopant material comprises a compound of the formula:

X—CH═CH—Y—CH═CH-Z

where X and Z are independently selected from the group consisting of a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic complex ring group and an unsubstituted aromatic complex ring group, said aromatic complex ring group having one nitrogen atom, and Y is selected from the group consisting of a divalent aromatic group, and a divalent aromatic complex ring group having one nitrogen atom.

26. The device of claim 2 wherein the dopant material comprises a compound of the formula:

X—(CH═CH) n -Z

where X and Z are independently selected from the group consisting of a substituted aromatic group, an unsubstituted aromatic group, a substituted aromatic complex ring group, and an unsubstituted aromatic complex ring group, said aromatic complex ring group having one nitrogen atom, and n equals 1, 2, or 3.

27. The device of claim 2 wherein the dopant material comprises a 4,4′-(1,4-phenylenedi-2,1-ethenediyl)bis(N,N-aryl)arylamine compound.

28. The device of claim 2 wherein the dopant material comprises 4,4′-(9,10-anthracenediyldi-2,1-ethenediyl)bis(N,N-bis(4-methylphenyl)benzenamine.

29. The device of claim 2 wherein the dopant material comprises 4,4′-(1,4-naphthalenediyldi-2,1-ethenediyl)bis(N,N-bis(4-methylphenyl)benzenamine.

30. The device of claim 2 wherein the dopant material comprises 4,4′-(1,4-phenylenedi-2,1-ethenediyl)bis(N,N-(4-tolyl))benzeneamine.

31. The device of claim 2 wherein the dopant comprises a fluorescent aromatic compound.

32. The device of claim 2 wherein the dopant comprises a fluorescent dye.

33. The device of claim 2 wherein the dopant comprises a phosphorescent dye.

34. The device of claim 2 wherein the dopant is selected to provide emission between 300 and 1700 nm.

35. The device of claim 2 wherein the dopant is selected to provide an emitted light having a blue hue.

36. The device of claim 2 wherein the dopant is selected to provide an emitted light having a green hue.

37. The device of claim 2 wherein the dopant is selected to provide an emitted light having a red hue.

38. The device of claim 2 wherein the dopant comprises a fluorescent dye selected from the group sonsisting of anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran, thiopyran, polymethine, pyrilium, thiapyrilium, napthyridine, fluoranthene, furan, indole, thiaphene, benzoxanthene, pyrene, peropyrene, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, fluorene, anthanthrene, bisanthrene, N,N,N′,N′-substituted benzidene, N,N,N′,N′-tetrarylbenzidene, carbostyryl, acridine, quinoline, purine, phenazine, phenoxazine, and phenanthroline compounds, which compounds may be substituted or unsusbstituted.

39. The device of claim 2 wherein the dopant comprises a compound selected form the group consisting of a benzoxazole compound, a benzthiazole compound, an oxazole compound, a triazole compound, an oxadiazole compound and a benzimidazole compound, any of which may be substituted or unsusbstituted.

40. The device of claim 38 wherein the dopant comprises a fluorescent dye including a compound selected from the group consisting of a substituted or unsubstituted benzo-, dibenzo-, naphtha-, and dinaphtho-fused derivatives, and combinations thereof.

41. The device of claim 1 wherein the host material includes a polymeric material.

42. The device of claim 41 wherein the host material is a blend of two or more polymeric materials.

43. The device of claim 1 wherein the host material is a combination of nonpolymeric and polymeric material.

44. The device of claim 42 wherein the polymeric materials are unsubstituted poly(p-phenylenevinylene) derivatives.

45. The device of claim 42 wherein the polymeric materials are substituted and unsubstituted poly(p-phenylene) derivatives.

46. The device of claim 41 wherein the polymeric materials are substituted and unsubstituted polyfluorene derivatives.

47. The device of claim 41 wherein the polymeric materials are substituted and unsubstituted poly(p-pyridine).

48. The device of claim 41 wherein the polymeric materials are substituted and unsubstituted poly(p-pyridalvinylene) derivatives.

49. The device of claim 41 wherein the polymeric materials are substituted and unsubstituted poly(p-phenylene) ladder and step-ladder polymers.

Assignments (8)
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST) INC.; KODAK AMERICAS LTD.; KODAK REALTY INC.; LASER PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES LTD.; NPEC INC.
Reel/Frame 052773/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049814/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (FIRST LIEN) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC; KODAK AMERICAS, LTD.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE
Reel/Frame 031158/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (ABL) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 031162/0117 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (SECOND LIEN) Recorded Sep 5, 2013
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 031159/0001 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 5, 2013
From: CITICORP NORTH AMERICA, INC., AS SENIOR DIP AGENT; WILMINGTON TRUST, NATIONAL ASSOCIATION, AS JUNIOR DIP AGENT
To: EASTMAN KODAK COMPANY; PAKON, INC.
Reel/Frame 031157/0451 →
PATENT SECURITY AGREEMENT Recorded Apr 1, 2013
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 030122/0235 →
SECURITY INTEREST Recorded Feb 21, 2012
From: EASTMAN KODAK COMPANY; PAKON, INC.
To: CITICORP NORTH AMERICA, INC., AS AGENT
Reel/Frame 028201/0420 →