IP Library › Granted Patent US 10,586,934

Granted Patent B2

US 10,586,934 · App. 16/261,698 · Granted Mar 10, 2020

Light-emitting element

Inventors: Satoko Shitagaki (Kanagawa, JP); Satoshi Seo (Kanagawa, JP); Nobuharu Ohsawa (Kanagawa, JP); Hideko Inoue (Kanagawa, JP); Kunihiko Suzuki (Kanagawa, JP)

Assignee: Semiconductor Energy Laboratory Co., Ltd.

H01L51/0085 C07D209/86 C07D239/26 C07D241/12 C07D333/76 C07D409/10 C07D471/04 C07F15/0033 C09K11/025 C09K11/06 H01L51/006 H01L51/0059 H01L51/0061 H01L51/0072 H01L51/0074 H01L51/5016 C09K2211/1007 C09K2211/1074 C09K2211/185 H01L51/0052 H01L51/0056 H01L51/0058 H01L2251/5376 H01L2251/5384 H01L2251/552

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Quick Facts

Patent No.: US 10,586,934
App. No.: 16/261,698
Granted: Mar 10, 2020
Kind: B2

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Abstract

A light-emitting element having high external quantum efficiency is provided. A light-emitting element having a long lifetime is provided. A light-emitting element is provided which includes a light-emitting layer containing a phosphorescent compound, a first organic compound, and a second organic compound between a pair of electrodes, in which a combination of the first organic compound and the second organic compound forms an exciplex (excited complex). The light-emitting element transfers energy by utilizing an overlap between the emission spectrum of the exciplex and the absorption spectrum of the phosphorescent compound and thus has high energy transfer efficiency. Therefore, a light-emitting element having high external quantum efficiency can be obtained.

Claims (168)

1. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an emission spectrum of the exciplex overlaps with a longest wavelength side absorption band in an absorption spectrum of the phosphorescent compound,

wherein one of the first organic compound and the second organic compound is a carbazole compound,

wherein the carbazole compound comprises a carbazol-3-yl group, and

wherein an absolute value of a difference between an energy value of a peak of the emission spectrum and an energy value of a peak of the longest wavelength side absorption band in the absorption spectrum is 0.2 eV or less.

2. The light-emitting element according to claim 1 ,

wherein the first organic compound is a heterocyclic compound.

3. The light-emitting element according to claim 1 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

4. The light-emitting element according to claim 1 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

5. The light-emitting element according to claim 1 ,

wherein one of the electrodes comprises ytterbium.

6. The light-emitting element according to claim 1 ,

wherein the difference between the energy value of the peak of the emission spectrum and the energy value of the peak of the longest wavelength side absorption band in the absorption spectrum is 0.1 eV or less.

7. The light-emitting element according to claim 1 ,

wherein the longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

8. The light-emitting element according to claim 1 ,

wherein a level of a triplet excitation energy of each of the first organic compound and second organic compound is higher than a level of a triplet excitation energy of the phosphorescent compound.

9. The light-emitting element according to claim 1 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with the longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

10. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an emission spectrum of the exciplex overlaps with a longest wavelength side absorption band in an absorption spectrum of the phosphorescent compound,

wherein one of the first organic compound and the second organic compound is a carbazole compound,

wherein the carbazole compound comprises a first carbazole ring and a second cabazole ring,

wherein the first carbazole ring at 3-position bonds to the second carbazole ring at 3-position, and

11. The light-emitting element according to claim 10 ,

wherein the first organic compound is a heterocyclic compound.

12. The light-emitting element according to claim 10 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

13. The light-emitting element according to claim 10 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

14. The light-emitting element according to claim 10 ,

wherein one of the electrodes comprises ytterbium.

15. The light-emitting element according to claim 10 ,

16. The light-emitting element according to claim 10 ,

wherein the longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

17. The light-emitting element according to claim 10 ,

wherein a level of a triplet excitation energy of each of the first organic compound and second organic compound is higher than a level of a triplet excitation energy of the phosphorescent compound.

18. The light-emitting element according to claim 10 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with the longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

19. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an emission spectrum of the exciplex overlaps with a longest wavelength side absorption band in an absorption spectrum of the phosphorescent compound,

wherein one of the first organic compound and the second organic compound is a carbazole compound,

wherein the carbazole compound comprises two cabazole rings, and

20. The light-emitting element according to claim 19 ,

wherein the two cabazole rings directly bond to each other.

21. The light-emitting element according to claim 19 ,

wherein the first organic compound is a heterocyclic compound.

22. The light-emitting element according to claim 19 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

23. The light-emitting element according to claim 19 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

24. The light-emitting element according to claim 19 ,

wherein one of the electrodes comprises ytterbium.

25. The light-emitting element according to claim 19 ,

26. The light-emitting element according to claim 19 ,

wherein the longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

27. The light-emitting element according to claim 19 ,

wherein a level of a triplet excitation energy of each of the first organic compound and second organic compound is higher than a level of a triplet excitation energy of the phosphorescent compound.

28. The light-emitting element according to claim 19 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with the longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

29. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an emission spectrum of the exciplex overlaps with a longest wavelength side absorption band in an absorption spectrum of the phosphorescent compound,

wherein a peak wavelength of the longest wavelength side absorption band is in a range from 490 nm to 530 nm, and

wherein an absolute value of a difference between an energy value of a peak of the emission spectrum and an energy value of the peak of the longest wavelength side absorption band in the absorption spectrum is 0.2 eV or less.

30. The light-emitting element according to claim 29 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

31. The light-emitting element according to claim 29 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

32. The light-emitting element according to claim 29 ,

wherein one of the electrodes comprises ytterbium.

33. The light-emitting element according to claim 29 ,

34. The light-emitting element according to claim 29 ,

wherein the longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

35. The light-emitting element according to claim 29 ,

wherein a level of a triplet excitation energy of the exciplex is higher than a level of a triplet excitation energy of the phosphorescent compound.

36. The light-emitting element according to claim 29 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with the longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

37. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an absorption spectrum of the phosphorescent compound comprises a first absorption peak and a second absorption peak,

wherein the first absorption peak is located on a longest wavelength side in the absorption spectrum of the phosphorescent compound,

wherein the second absorption peak is located on a shorter wavelength side than the first absorption peak in the absorption spectrum,

wherein the second absorption peak is located next to the first absorption peak, and

wherein a peak of an emission spectrum of the exciplex is located on a longer wavelength side than the second absorption peak, and

wherein an absolute value of a difference between an energy value of the peak of the emission spectrum and an energy value of a peak of a longest wavelength side absorption band in the absorption spectrum is 0.2 eV or less.

38. The light-emitting element according to claim 37 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

39. The light-emitting element according to claim 37 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

40. The light-emitting element according to claim 37 ,

wherein one of the electrodes comprises ytterbium.

41. The light-emitting element according to claim 37 ,

42. The light-emitting element according to claim 37 ,

wherein a longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

43. The light-emitting element according to claim 37 ,

wherein a level of a triplet excitation energy of the exciplex is higher than a level of a triplet excitation energy of the phosphorescent compound.

44. The light-emitting element according to claim 37 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with a longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

45. A light-emitting element comprising:

a pair of electrodes; and

a light-emitting layer comprising a phosphorescent compound, a first organic compound and a second organic compound between the pair of electrodes,

wherein the first organic compound and the second organic compound are selected so as to form an exciplex,

wherein an absorption spectrum of the phosphorescent compound comprises a first absorption peak and a second absorption peak,

wherein the first absorption peak is located on a longest wavelength side in the absorption spectrum of the phosphorescent compound,

wherein the second absorption peak is located on a shorter wavelength side than the first absorption peak in the absorption spectrum,

wherein the second absorption peak is located next to the first absorption peak,

wherein a peak of an emission spectrum of the exciplex is closer to the first absorption peak than the second absorption peak, and

46. The light-emitting element according to claim 45 , further comprising:

a hole injection layer,

wherein the hole injection layer comprise an aromatic amine compound and an electron acceptor.

47. The light-emitting element according to claim 45 , further comprising:

a hole transport layer,

wherein the hole transport layer comprises an aromatic amine compound, and

wherein the aromatic amine compound comprises a fluorenyl group.

48. The light-emitting element according to claim 45 ,

wherein one of the electrodes comprises ytterbium.

49. The light-emitting element according to claim 45 ,

50. The light-emitting element according to claim 45 ,

wherein a longest wavelength side absorption band is an absorption wavelength corresponding to direct transition from a singlet ground state to a triplet excitation state.

51. The light-emitting element according to claim 45 ,

wherein a level of a triplet excitation energy of the exciplex is higher than a level of a triplet excitation energy of the phosphorescent compound.

52. The light-emitting element according to claim 45 ,

wherein one of the first organic compound and the second organic compound has higher content than the other, and

wherein a phosphorescence spectrum of the one overlaps with a longest wavelength side absorption band in the absorption spectrum of the phosphorescent compound.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 31, 2019

From: SHITAGAKI, SATOKO; SEO, SATOSHI; OHSAWA, NOBUHARU; INOUE, HIDEKO; SUZUKI, KUNIHIKO

To: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Reel/Frame 048199/0761 →

Priority Claims (1)

JP 2011-031462 · Feb 16, 2011 · national

Continuity (3)

Continuation 15454055 · Mar 9, 2017

Continuation 13370679 · Feb 10, 2012

Related Publication 20190157577A1 · May 23, 2019

Cited By (5)

US 12,225,748 US 12,581,794 US 12,648,355 US 12,652,950 US 12,672,453