IP Library › Granted Patent US 11,158,808
Granted Patent B2
US 11,158,808 · App. 16/842,486 · Granted Oct 26, 2021

Organic light emitting display device

Inventors: Jungkeun Kim (Seoul, KR); Dohan Kim (Goyang-si, KR); Jeongdae Seo (Incheon, KR); Hyoseok Kim (Daejeon, KR); Heungwoo Choi (Daejeon, KR); Wanpyo Hong (Daejeon, KR)
Assignees: LG Display Co., Ltd.; LG Chem, Ltd.
H01L51/0052C07C255/47C07D213/61C09K11/06H01L51/0053H01L51/0064H01L51/0067H01L51/5056H01L51/5278C07C2603/10C09K2211/1007C09K2211/1011C09K2211/1029H01L51/506H01L51/5012H01L51/5064H01L51/5088H01L51/5206H01L51/5221
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 11,158,808
App. No.
16/842,486
Granted
Oct 26, 2021
Kind
B2
Abstract

An organic light emitting display device is provided. The organic light emitting display device may include at least one light emitting part between an anode and a cathode, and the at least one light emitting part having at least one organic layer and a light emitting layer, wherein the at least one organic layer comprises a compound represented by Chemical Formula 1 or 2.

Claims (85)

1. An organic light emitting display device, comprising:

at least one light emitting part between an anode and a cathode,

wherein the at least one light emitting part comprises at least one organic layer,

wherein the at least one organic layer comprises a first P-type charge generation layer,

wherein the first P-type charge generation layer comprises a compound represented by Chemical Formula 1:

where

R 1 to R 6 include independently one among hydrogen, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted or unsubstituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group, and at least one of R 1 to R 6 comprises a cyano group, and

Z 1 and Z 2 are independently represented by the following Chemical Formula 2:

where A and B independently represent one among a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted or unsubstituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group,

wherein Z 1 and Z 2 are attached via a double bond between a carbon atom bound to A and B of Chemical Formula 2 and the indacene ring of Chemical Formula 1.

2. The organic light emitting display device of claim 1 , wherein a substituent of the substituted aryl group, the substituted heteroaryl group, the substituted alkyl group, the substituted alkoxy group or the substituted ether group includes an alkyl with 2 to 12 carbon atoms, an aryl with 6 to 15 carbon atoms, a hetero alkyl with 1 to 15 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, or a trimethylsilyl group.

3. The organic light emitting display device of claim 1 , wherein the compound represented by Chemical Formula 1 is one among the following compounds:

4. The organic light emitting display device of claim 1 , wherein a dopant of the first P-type charge generation layer includes the compound represented by Chemical Formula 1.

5. The organic light emitting display device of claim 3 , wherein a dopant of the first P-type charge generation layer includes the compound represented by Chemical Formula 1.

6. The organic light emitting display device of claim 1 ,

wherein the at least one light emitting part includes a first light emitting part and a second light emitting part,

wherein the first light emitting part includes a first light emitting layer, and

wherein the second light emitting part includes a second light emitting layer.

7. The organic light emitting display device of claim 6 , wherein:

the first light emitting layer emits light of a color of at least one among red, green, and blue; and

the second light emitting layer emits light of a color of at least one among red, green, and blue.

8. The organic light emitting display device of claim 6 , wherein the first light emitting layer and the second light emitting layer emit light of the same color.

9. The organic light emitting display device of claim 6 , wherein the at least one organic layer includes a hole injection layer including the compound represented by Chemical Formula 1.

10. The organic light emitting display device of claim 3 , wherein the at least one organic layer includes a hole injection layer including the compound represented by Chemical Formula 1.

11. The organic light emitting display device of claim 6 , wherein:

the first light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer; and

the second light emitting layer includes a yellow-green emitting layer, a green emitting layer, a combination of a yellow-green emitting layer and a green emitting layer, a combination of a yellow emitting layer and a red emitting layer, a combination of a green emitting layer and a red emitting layer, or a combination of a yellow-green emitting layer and a red emitting layer.

12. The organic light emitting display device of claim 1 , wherein the at least one light emitting part includes a first light emitting part, a second light emitting part, and a third light emitting part, and

the first light emitting part includes a first light emitting layer, the second light emitting part includes a second light emitting layer, and the third light emitting part includes a third light emitting layer.

13. The organic light emitting display device of claim 12 , wherein:

the first light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer;

the second light emitting layer includes a yellow-green emitting layer, a green emitting layer, a combination of a yellow-green emitting layer and a green emitting layer, a combination of a yellow emitting layer and a red emitting layer, a combination of a green emitting layer and a red emitting layer, or a combination of a yellow-green emitting layer and a red emitting layer; and

the third light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer.

14. The organic light emitting display device of claim 12 , further comprising a second P-type charge generation layer between the second light emitting part and the third light emitting part, a dopant of the second P-type generation layer including the compound.

15. An organic light emitting display device, comprising:

a first light emitting part between an anode and a cathode;

a second light emitting part on the first light emitting part; and

a charge generation layer having a first P-type charge generation layer between the first light emitting part and the second light emitting part,

wherein the first P-type charge generation layer comprises a compound represented by Chemical Formula 1:

where

R 1 to R 6 each independently represents one among a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group, and at least one among R 1 to R 6 comprises a cyano group, and

Z 1 and Z 2 are independently represented by the following Chemical Formula 2:

where A and B independently represent one among a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted or unsubstituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group,

wherein Z 1 and Z 2 are attached via a double bond between a carbon atom bound to A and B of Chemical Formula 2 and the indacene ring of Chemical Formula 1.

16. The organic light emitting display device of claim 15 , wherein a substituent of the substituted aryl group, the substituted heteroaryl group, the substituted alkyl group, the substituted alkoxy group, or the substituted ether group includes an alkyl with 2 to 12 carbon atoms, an aryl with 6 to 15 carbon atoms, a hetero alkyl with 1 to 15 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, or a trimethylsilyl group.

17. The organic light emitting display device of claim 15 , wherein the compound represented by Chemical Formula 1 is one among the following compounds:

18. The organic light emitting display device of claim 15 , wherein a dopant of the first P-type charge generation layer includes the compound represented by Chemical Formula 1.

19. The organic light emitting display device of claim 17 , wherein a dopant of the first P-type charge generation layer includes the compound represented by Chemical Formula 1.

20. The organic light emitting display device of claim 15 , wherein the first light emitting part includes a first light emitting layer and the second light emitting part includes a second light emitting layer.

21. The organic light emitting display device of claim 20 , wherein:

the first light emitting layer emits light of a color of at least one among red, green, and blue; and

the second light emitting layer emits light of a color of at least one among red, green, and blue.

22. The organic light emitting display device of claim 20 , wherein the first light emitting layer and the second light emitting layer emit light of the same color.

23. The organic light emitting display device of claim 17 , wherein the first light emitting part further includes a hole injection layer including the compound represented by Chemical Formula 1.

24. The organic light emitting display device of claim 20 , wherein the first light emitting part further includes a hole injection layer including the compound represented by Chemical Formula 1.

25. The organic light emitting display device of claim 20 , wherein:

the first light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer; and

the second light emitting layer includes a yellow-green emitting layer, a green emitting layer, a combination of a yellow-green emitting layer and a green emitting layer, a combination of a yellow emitting layer and a red emitting layer, a combination of a green emitting layer and a red emitting layer, or a combination of a yellow-green emitting layer and a red emitting layer.

26. The organic light emitting display device of claim 15 , wherein:

the at least one light emitting part includes a first light emitting part, a second light emitting part, and a third light emitting part,

the first light emitting part includes a first light emitting layer,

the second light emitting part includes a second light emitting layer, and

the third light emitting part includes a third light emitting layer.

27. The organic light emitting display device of claim 26 , wherein:

the first light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer;

the second light emitting layer includes a yellow-green emitting layer, a green emitting layer, a combination of a yellow-green emitting layer and a green emitting layer, a combination of a yellow emitting layer and a red emitting layer, a combination of a green emitting layer and a red emitting layer, or a combination of a yellow-green emitting layer and a red emitting layer; and

the third light emitting layer includes a blue light emitting layer, a dark blue emitting layer, a sky blue emitting layer, a combination of a blue light emitting layer and a red light emitting layer, a combination of a blue light emitting layer and a yellow-green emitting layer, or a combination of a blue light emitting layer and a green emitting layer.

28. The organic light emitting display device of claim 26 , further comprising a second P-type charge generation layer between the second light emitting part and the third light emitting part, and a dopant of the second P-type generation layer including the compound represented by Chemical Formula 1.

29. An organic light emitting display device, comprising:

a hole injection layer on an anode;

a hole transport layer on the hole injection layer;

a light emitting layer on the hole transport layer;

an electron transport layer on the light emitting layer; and

a cathode on the electron transport layer,

wherein the hole injection layer comprises a compound represented by Chemical Formula 1:

where

R 1 to R 6 each independently represents one among a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group, and at least one among R 1 to R 6 comprises a cyano group, and

Z 1 and Z 2 are independently represented by the following Chemical Formula 2:

where A and B independently represent one among a hydrogen atom, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group with 1 to 12 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a substituted or unsubstituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 12 carbon atoms, a substituted or unsubstituted ether group with 2 to 12 carbon atoms, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, and a trimethylsilyl group,

wherein Z 1 and Z 2 are attached via a double bond between a carbon atom bound to A and B of Chemical Formula 2 and the indacene ring of Chemical Formula 1.

30. The organic light emitting display device of claim 29 , wherein a substituent of the substituted aryl group, the substituted heteroaryl group, the substituted alkyl group, the substituted alkoxy group, or the substituted ether group includes an alkyl with 2 to 12 carbon atoms, an aryl with 6 to 15 carbon atoms, a hetero alkyl with 1 to 15 carbon atoms and 1 to 4 heteroatoms one among O, N, S, and Si, a cyano group, a fluorine group, a trifluoromethyl group, a trifluoromethoxy group, or a trimethylsilyl group.

31. The organic light emitting display device of claim 29 , wherein the compound represented by Chemical Formula 1 is one among the following compounds:

32. The organic light emitting display device of claim 31 , wherein the hole injection layer includes the compound.

33. The organic light emitting display device of claim 29 , further comprising an electron injection layer on the electron transport layer.

34. The organic light emitting display device of claim 29 , wherein the light emitting layer emits light of a color of at least one among red, green, and blue.

Priority Claims (2)
KR 10-2015-0171452 · Dec 3, 2015 · national
KR 10-2016-0057107 · May 10, 2016 · national
Continuity (2)
Continuation 15250214 · Aug 29, 2016
Related Publication 20200235302A1 · Jul 23, 2020