IP Library › Granted Patent US 10,069,073
Granted Patent B2
US 10,069,073 · App. 14/553,601 · Granted Sep 4, 2018

Organic compounds and organic light emitting device comprising the same

Inventors: Youngju Ryu (Paju-si, KR); Seungjae Lee (Paju-si, KR); Jongkwan Bin (Paju-si, KR); Joonghwan Yang (Gwangmyeong-si, KR); Bangsook Lee (Seoul, KR); Bomin Seo (Paju-si, KR); Inae Shin (Paju-si, KR)
Assignee: LG DISPLAY CO., LTD.
H01L51/005H01L51/0051H01L51/5088
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Quick Facts
Patent No.
US 10,069,073
App. No.
14/553,601
Granted
Sep 4, 2018
Kind
B2
Abstract

Provided are organic compounds capable of improving the efficiency of light emission and lowering the driving voltage of an organic light emitting device, and an organic light emitting device including the same. The organic compounds include an organic compound of chemical formula 1:

Claims (61)

1. An organic compound of chemical formula 1:

wherein R 1 , R 2 , R 3 and R 4 each represent, independently of each other, a hydrogen atom, a deuterium atom, —OH, —CN, —NO 2 , —CF 3 , a fluoroalkyl group, a halogen group, a carboxyl group, a carbonyl group, a C1-C18 substituted or unsubstituted alkoxy group, a C6 or more substituted or unsubstituted aromatic group, a C5 or more substituted or unsubstituted heteroaromatic group, a C6 or more substituted or unsubstituted aryloxy group, C5 or more substituted or unsubstituted heteroaryloxy group, a C1-C18 amine group, an amine group containing a C6 or more substituted or unsubstituted aromatic group, or an amine group containing a C5 or more substituted or unsubstituted heteroaromatic group;

at least one of R 1 , R 2 , R 3 and R 4 represent a C6 or more substituted or unsubstituted aromatic group, a C5 or more substituted or unsubstituted heteroaromatic group, a C1-C18 amine group, an amine group containing a C6 or more substituted or unsubstituted aromatic group, an amine group containing a C5 or more substituted or unsubstituted heteroaromatic group;

X 1 and Y 1 each represent, independently from each other, (a), (b), or (d):

and

R 5 , R 6 and R 7 each represent, independently from each other, a hydrogen atom, a deuterium atom, —OH, —CN, —NO 2 , —CF 3 , a fluoroalkyl group, a halogen group, a carboxyl group, a carbonyl group, a C1-C18 substituted or unsubstituted alkyl group, a C1-C18 substituted or unsubstituted alkoxy group, a C6 or more substituted or unsubstituted aromatic group, a C6 or more substituted or unsubstituted aryloxy group, a C5 or more substituted or unsubstituted heteroaromatic group, or a C5 or more substituted or unsubstituted heteroaryloxy group,

wherein X 1 and Y 1 are different each other, and

wherein R 5 and R 6 are optionally linked to each other to form a ring.

2. The organic compound of claim 1 , wherein the compound of chemical formula 1 is selected from:

3. An organic compound of chemical formula 2:

wherein

B 1 and B 2 each represent, independently from each other, a hydrogen atom, a deuterium atom, —CN, —NO 2 , —CF 3 , —F, a fluoroalkyl group, or a halogen group;

R 8 to R 17 each represent, independently from each other, a hydrogen atom, a deuterium atom, —OH, —CN, —NO 2 , —CF 3 , a fluoroalkyl group, a halogen group, a carboxyl group, a carbonyl group, a C1-C18 substituted or unsubstituted alkyl group, a C1-C18 substituted or unsubstituted alkoxy group, a C6 or more substituted or unsubstituted aromatic group, a C5 or more substituted or unsubstituted heteroaromatic group, a C6 or more substituted or unsubstituted aryloxy group, C5 or more substituted or unsubstituted heteroaryloxy group, a C1-C18 amine group, an amine group containing a C6 or more substituted or unsubstituted aromatic group, an amine group containing a C5 or more substituted or unsubstituted heteroaromatic group, a silyl group containing a C1-C27 alkyl group or a C6 or more substituted or unsubstituted aromatic group, or a silyl group containing a C5 or more substituted or unsubstituted heteroaromatic group, and

at least one of R 8 to R 17 represents —CN, —NO 2 , —CF 3 , —F, or a fluoroalkyl group;

X 2 and Y 2 each represent, independently from each other, (f), or (h):

and

A 3 represents a hydrogen atom, a deuterium atom, —OH, —CN, —NO 2 , —CF 3 , a fluoroalkyl group, a halogen group, a carboxyl group, a carbonyl group, a C1-C18 substituted or unsubstituted alkyl group, a C1-C18 substituted or unsubstituted alkoxy group, a C6 or more substituted or unsubstituted aromatic group, a C6 or more substituted or unsubstituted aryloxy group, a C5 or more substituted or unsubstituted heteroaromatic group, or a C5 or more substituted or unsubstituted heteroaryloxy group.

4. The organic compound of claim 3 , wherein the organic compound of chemical formula 2 is selected from:

5. An organic light emitting device comprising a light emitting layer between an anode and a cathode, and at least one organic film between the anode and the light emitting layer,

wherein the organic film contains the organic compound of claim 1 .

6. The organic light emitting device of claim 5 , wherein the organic film is at least one selected from a hole injection layer, a hole transport layer, and a hole buffer layer.

7. The organic light emitting device of claim 6 , wherein the hole injection layer is formed of only the organic compound.

8. The organic light emitting device of claim 6 , wherein the hole buffer layer is disposed between the hole injection layer and the hole transport layer, and contacted with the anode.

9. The organic light emitting device of claim 6 , wherein the hole buffer layer is disposed between the hole injection layer and the hole transport layer.

10. The organic light emitting device of claim 8 , wherein the hole buffer layer is formed of only the organic compound, or formed of a host material and the organic compound.

11. The organic light emitting device of claim 10 , wherein the host material is a material of the hole transport layer.

12. The organic light emitting device of claim 6 , wherein the hole transport layer is disposed on the hole injection layer, and formed of a material of the hole transport layer and the organic compound.

13. An organic light emitting device comprising a plurality of stacks between an anode and a cathode, each of the stacks including a light emitting layer, the plurality of stacks including a first stack and a second stack,

wherein the first stack including a first light emitting layer, the second stack includes a second light emitting layer, and a charge generation layer is disposed between the first stack and the second stack,

wherein the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer, and

wherein the P-type charge generation layer contains the organic compound of claim 1 .

14. The organic light emitting device of claim 13 , wherein the first stack includes at least one organic film disposed between the anode and the first light emitting layer, the organic film being at least one of a hole injection layer, a first hole transport layer, and a hole buffer layer.

15. The organic light emitting device of claim 13 , wherein the first stack includes a first hole transport layer, the P-type charge generation layer is formed of only the organic compound or formed of a host material or the organic compound.

16. The organic light emitting device of claim 15 , wherein the host material is a material of the hole transport layer.

17. The organic light emitting device of claim 15 , wherein the second stack includes a second hole transport layer disposed between the P-type charge generation layer and the second light emitting layer.

18. The organic light emitting device of claim 15 , wherein the P-type charge generation layer is contacted with the second light emitting layer.

19. The organic light emitting device of claim 14 , wherein the hole injection layer is formed of only the organic compound.

20. The organic light emitting device of claim 14 , wherein the hole buffer layer is disposed between the anode and the first hole transport layer, and contacted with the anode.

21. The organic light emitting device of claim 14 , wherein the hole buffer layer is disposed between the hole injection layer and the first hole transport layer.

22. The organic light emitting device of claim 20 , wherein the hole buffer layer is formed of only the organic compound, or formed of a host material and the organic compound.

23. The organic light emitting device of claim 22 , wherein the host material is a material of the first hole transport layer.

24. The organic light emitting device of claim 14 , wherein the first hole transport layer is disposed on the hole injection layer, and formed of a material of the first hole transport layer and the organic compound.

25. The organic compound of claim 1 , wherein the organic compound is contained in at least one organic film of an organic light emitting device.

26. The organic compound of claim 1 , wherein the organic compound has electron accepting capacity.

27. The organic compound of claim 25 , wherein the organic film is at least one selected from a hole injection layer, a hole transport layer, and a hole buffer layer.

28. The organic compound of claim 27 , wherein the hole injection layer is formed of only the organic compound.

29. The organic compound of claim 27 , wherein the hole buffer layer is disposed between the hole injection layer and the hole transport layer, and contacted with the anode, the hole buffer layer is disposed between the hole injection layer and the hole transport layer, and the hole buffer layer is formed of only the organic compound, or formed of a host material and the organic compound.

30. The organic compound of claim 27 , wherein the hole transport layer is disposed on the hole injection layer, and formed of a material of the hole transport layer and the organic compound.

31. The organic compound of claim 1 , wherein the compound is contained in an organic light emitting device,

wherein the organic light emitting device comprises comprising a plurality of stacks between an anode and a cathode, each of the stacks including a light emitting layer, the plurality of stacks including a first stack and a second stack,

wherein the first stack includes a first light emitting layer, the second stack includes a second light emitting layer, and a charge generation layer is disposed between the first stack and the second stack,

wherein the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer, and

wherein the compound is contained in the P-type charge generation layer.

32. The organic compound of claim 31 , wherein the first stack includes at least one organic film disposed between the anode and the first light emitting layer, the organic film being at least one of a hole injection layer, a first hole transport layer, and a hole buffer layer.

33. The organic compound of claim 31 , wherein the first stack includes a first hole transport layer, the P-type charge generation layer is formed of only the organic compound or formed of a host material or the organic compound, wherein the host material is a material of the hole transport layer.

34. The organic compound of claim 31 , wherein the second stack includes a second hole transport layer disposed between the P-type charge generation layer and the second light emitting layer, and the P-type charge generation layer is contacted with the second light emitting layer.

35. The organic compound of claim 32 , wherein the hole injection layer is formed of only the organic compound.

36. The organic compound of claim 32 , wherein the hole buffer layer is disposed between the anode and the first hole transport layer, and contacted with the anode, the hole buffer layer is disposed between the hole injection layer and the first hole transport layer, and the hole buffer layer is formed of only the organic compound, or formed of a host material and the organic compound.

37. The organic compound of claim 32 , wherein the first hole transport layer is disposed on the hole injection layer, and formed of a material of the first hole transport layer and the organic compound.

38. An organic compound which is a benzoquinone derivative comprising a substituent having an electron accepting capacity, wherein the organic compound is capable of increasing power efficiency, improving power consumption, and lowering the driving voltage,

wherein the organic compound is selected from:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 26, 2014
From: RYU, YOUNGJU; LEE, SEUNGJAE; BIN, JONGKWAN; YANG, JOONGHWAN; LEE, BANGSOOK; SEO, BOMIN; SHIN, INAE
To: LG DISPLAY CO., LTD.
Reel/Frame 034273/0133 →
Priority Claims (1)
KR 10-2013-0149385 · Dec 3, 2013 · national
Continuity (1)
Related Publication 20150155490A1 · Jun 4, 2015