IP Library › Granted Patent US 11,332,474
Granted Patent B2
US 11,332,474 · App. 16/530,234 · Granted May 17, 2022

Compound and organic light-emission device

Inventors: Heejun Park (Paju-si, KR); Seonkeun Yoo (Gunpo-si, KR); Sangbeom Kim (Paju-si, KR); Soyoung Jang (Seoul, KR); Jicheol Shin (Seoul, KR)
Assignee: LG DISPLAY CO., LTD.
C07D493/04C07D495/04C07D497/04H01L51/006H01L51/0073H01L51/5016H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 11,332,474
App. No.
16/530,234
Granted
May 17, 2022
Kind
B2
Abstract

The present invention provides a novel compound of an amine derivative including a spiro compound. The novel compound has excellent hole transport characteristics. Thus, when the novel compound is applied to a hole transport layer, an auxiliary hole transport layer and an electron blocking layer of an organic light-emitting device, the device realizes low driving voltage, high efficiency, high thermal stability and long life-span. Further, when the novel compound is applied as a blue light-emitting material, the device realizes a low driving voltage and high efficiency.

Claims (35)

1. A compound represented by Chemical Formula 1:

wherein, in the Chemical Formula 1, each of R 1 to R 4 independently represents one selected from a group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a C1 to C30 alkoxy group and a C6 to C30 aryloxy group;

each of a and b independently denotes an integer of 0 to 4, wherein when a or b denotes an integer of 2 or greater, each R 1 is the same or different and each R 2 is the same or different,

each of c and d independently denotes an integer of 0 to 4, wherein when c or d denotes an integer of 2 or greater, each R 3 is the same or different and each R 4 is the same or different,

each of m and n independently denotes an integer of 0 to 4, wherein when m or n denotes an integer of 2 or greater, each A is the same or different and each B is the same or different,

each of o and p independently denotes an integer of 0 to 4, wherein when o or p denotes an integer of 2 or greater, each C is the same or different and each D is the same or different,

wherein 0≤a+m≤4, 0≤b+n≤4, 0≤c+o≤4 and 0≤d+p≤4;

X represents O or S; and

each of A to D is represented by Chemical Formula 2:

wherein, in the Chemical Formula 2, L represents a direct bond or represents one selected from a group consisting of a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C30 arylene group or a divalent group of a heteroaromatic ring having 6 to 30 aromatic ring atoms; and each of Ar 1 and Ar 2 independently represents one selected from a group consisting of a substituted or unsubstituted C6 to C60 aryl group or a monovalent group of a heteroaromatic ring having 6 to 60 aromatic ring atoms, wherein Ar 1 and Ar 2 are optionally bonded to each other to form a ring.

2. The compound of claim 1 , wherein each of Ar 1 and Ar 2 in the Chemical Formula 2 are independently selected from:

3. The compound of claim 1 , wherein the compound represented by Chemical Formula 1 is represented by one of following Chemical Formulas:

4. An organic light-emission device comprising:

an anode,

a cathode, and

at least one organic material layer therebetween, wherein the organic material layer comprises a compound of claim 3 .

5. The organic light-emission device of claim 4 , wherein the organic material layer includes at least one of a hole transport layer, an auxiliary hole transport layer and an electron blocking layer, wherein the at least one of the hole transport layer, the auxiliary hole transport layer and the electron blocking layer comprises the compound represented by Chemical Formula 1.

6. The organic light-emission device of claim 4 , wherein the organic material layer comprises a blue light-emission layer comprising the compound represented by Chemical Formula 1 as a blue light-emission material.

7. The organic light-emission device of claim 4 , wherein the organic material layer includes at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises the compound represented by Chemical Formula 1.

8. The organic light-emission device of claim 7 , wherein the electron transport layer comprises the compound represented by Chemical Formula 1.

9. The organic light-emission device of claim 7 , wherein the hole blocking layer comprises the compound represented by Chemical Formula 1.

10. The organic light-emission device of claim 4 , wherein the organic material layer comprises a blue light-emission layer, wherein the blue light-emission layer comprises the compound represented by Chemical Formula 1 as a phosphorescent host material.

11. An organic light-emission device comprising:

an anode,

a cathode, and

at least one organic material layer therebetween, wherein the organic material layer comprises a compound of claim 1 .

12. The organic light-emission device of claim 11 , wherein the organic material layer includes at least one of a hole transport layer, an auxiliary hole transport layer and an electron blocking layer, wherein the at least one of the hole transport layer, the auxiliary hole transport layer and the electron blocking layer comprises the compound represented by Chemical Formula 1.

13. The organic light-emission device of claim 12 , wherein the hole transport layer comprises the compound represented by Chemical Formula 1.

14. The organic light-emission device of claim 12 , wherein the auxiliary hole transport layer comprises the compound represented by Chemical Formula 1.

15. The organic light-emission device of claim 12 , wherein the electron blocking layer comprises the compound represented by Chemical Formula 1.

16. The organic light-emission device of claim 11 , wherein the organic material layer comprises a blue light-emission layer comprising the compound represented by Chemical Formula 1 as a blue light-emission material.

17. The organic light-emission device of claim 11 , wherein the organic material layer includes at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises the compound represented by Chemical Formula 1.

18. The organic light-emission device of claim 17 , wherein the electron transport layer comprises the compound represented by Chemical Formula 1.

19. The organic light-emission device of claim 17 , wherein the hole blocking layer comprises the compound represented by Chemical Formula 1.

20. The organic light-emission device of claim 11 , wherein the organic material layer comprises a blue light-emission layer, wherein the blue light-emission layer comprises the compound represented by Chemical Formula 1 as a phosphorescent host material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2019
From: PARK, HEEJUN; YOO, SEONKEUN; KIM, SANGBEOM; JANG, SOYOUNG; SHIN, JICHEOL
To: LG DISPLAY CO., LTD.
Reel/Frame 049943/0714 →
Priority Claims (1)
KR 10-2018-0091834 · Aug 7, 2018 · national
Continuity (1)
Related Publication 20200048273A1 · Feb 13, 2020