IP Library Granted Patent US 8,815,418
Granted Patent B2
US 8,815,418 · App. 13/295,572 · Granted Aug 26, 2014

Compound including fluorenyl group for organic photoelectric device and organic photoelectric device including the same

Inventors: Hyung-Sun Kim (Uiwang-si, KR); Ho-Jae Lee (Uiwang-si, KR); Eui-Su Kang (Uiwang-si, KR); Nam-Heon Lee (Uiwang-si, KR); Young-Sung Park (Uiwang-si, KR); Eun-Sun Yu (Uiwang-si, KR); Mi-Young Chae (Uiwang-si, KR)
Assignee: Cheil Industries, Inc.
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 8,815,418
App. No.
13/295,572
Granted
Aug 26, 2014
Kind
B2
Abstract

A compound for an organic photoelectric device, organic photoelectric device, and a display device, the compound being represented by the following Chemical Formula 1:

Claims (46)

1. A compound for an organic photoelectric device, the compound being represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1:

X 1 to X 3 are each independently N or CR, in which R is hydrogen or a C1 to C10 alkyl group and provided that at least one of X 1 to X 3 is N,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C18 arylene group,

Ar 3 and Ar 4 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, or Ar 3 and Ar 4 are fused to each other to provide a fused ring,

Ar 5 and Ar 6 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

R 1 and R 2 are each independently hydrogen or a C1 to C10 alkyl group, and

a and b are each independently 1 or 2.

2. The compound for an organic photoelectric device as claimed in claim 1 , wherein all of X 1 to X 3 of Chemical Formula 1 are N.

3. The compound for an organic photoelectric device as claimed in claim 1 , wherein Ar 1 and Ar 2 in Chemical Formula 1 are each independently a phenylene group, a naphthylene group, an anthracenylene group, or a combination thereof.

4. The compound for an organic photoelectric device as claimed in claim 1 , wherein Ar 3 to Ar 6 of Chemical Formula 1 are each independently a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a tetracenyl group, a pyrenyl group, a fluorenyl group, or a combination thereof.

5. The compound for an organic photoelectric device as claimed in claim 1 , wherein Ar 3 to Ar 6 of Chemical Formula 1 are each independently represented by one of the following Chemical Formulae 2a to 2c, or a combination thereof:

wherein, in Chemical Formulae 2a to 2c, R′ and R″ are each independently hydrogen, a C1 to C10 alkyl group, a C6 to C18 aryl group, or a combination thereof.

6. The compound for an organic photoelectric device as claimed in claim 1 , wherein the compound for an organic photoelectric device represented by Chemical Formula 1 is represented by the following Chemical Formula 3a or Chemical Formula 3b:

wherein, in Chemical Formulae 3a and 3b:

Ar 4 is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,

Ar 5 and Ar 6 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

R 1 and R 2 are each independently hydrogen or a C1 to C10 alkyl group,

R 3 and R 4 are each independently hydrogen, a C1 to C10 alkyl group, a C6 to C18 aryl group, or a combination thereof, and

a and b are each independently 1 or 2.

7. The compound for an organic photoelectric device as claimed in claim 1 , wherein the compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulae 4 to 35 and ad-1 to ad-4:

8. A compound for an organic photoelectric device, the compound being represented by the following Chemical Formula A-1:

wherein, in Chemical Formula A-1:

X 1 to X 3 are each independently N or CR, in which R is hydrogen or a C1 to C10 alkyl and provided that at least one of X 1 to X 3 is N,

Ar 1 is a single bond or a substituted or unsubstituted C6 to C18 arylene group,

Ar 2 and Ar 3 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

Ar 4 is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,

R 1 to R 3 are each independently hydrogen or a C1 to C10 alkyl group, and

R 4 and R 5 are each independently hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, or R 4 and R 5 are fused to an adjacent ring to provide a fused ring.

9. The compound for an organic photoelectric device as claimed in claim 1 , wherein the compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulae 4, 6 to 10, 12 to 16, 18 to 22, 24 to 35, and ad-1 to ad-4:

10. The compound for an organic photoelectric device as claimed in claim 8 , wherein the compound represented by Chemical Formula A-1 is represented by one of the following Chemical Formulae ad-6 to ad-14, and ad-16 to ad-24:

11. The compound for an organic photoelectric device as claimed in claim 1 , wherein the compound for an organic photoelectric device is a charge transport material or a host material.

12. The compound for an organic photoelectric device as claimed in claim 1 , wherein the compound for an organic photoelectric device has a glass transition temperature (T g ) of about 110° C. or higher and a thermal decomposition temperature (Td) of about 400° C. or higher.

13. The compound for an organic photoelectric device as claimed in claim 8 , wherein the compound represented by Chemical Formula A-1 is represented by one of the following Chemical Formulae ad-5 to ad-24:

14. The compound for an organic photoelectric device as claimed in claim 8 , wherein all of X 1 to X 3 of Chemical Formula A-1 are N.

15. The compound for an organic photoelectric device as claimed in claim 8 , wherein Ar 1 in Chemical Formula A-1 is a phenylene group, a naphthylene group, an anthracenylene group, or a combination thereof.

16. The compound for an organic photoelectric device as claimed in claim 8 , wherein Ar 2 to Ar 4 in Chemical Formula A-1 are each independently represented by one of the following Chemical Formulae 2a to 2c, or combination thereof:

wherein, in Chemical Formula 2a to 2c, R′ and R″ are each independently hydrogen, a C1 to C10 alkyl group, a C6 to C18 aryl group, or a combination thereof.

17. An organic photoelectric device, comprising:

an anode;

a cathode; and

an organic thin layer between the anode and the cathode,

wherein the organic thin layer includes the compound for an organic photoelectric device as claimed in claim 1 .

18. The organic photoelectric device as claimed in claim 17 , wherein the organic thin layer includes an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), a hole blocking layer, an electron transport layer (ETL), an electron injection layer (EIL), an electron blocking layer, or a combination thereof.

19. The organic photoelectric device as claimed in claim 17 , wherein the organic thin layer further includes a dopant.

20. A display device comprising the organic photoelectric device as claimed in claim 17 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2011
From: KIM, HYUNG-SUN; LEE, HO-JAE; KANG, EUI-SU; LEE, NAM-HEON; PARK, YOUNG-SUNG; YU, EUN-SUN; CHAE, MI-YOUNG
To: CHEIL INDUSTRIES, INC.
Reel/Frame 027222/0113 →
Priority Claims (1)
KR 10-2009-0042706 · May 15, 2009 · national
Continuity (2)
Continuation PCTKR2010003071 · May 14, 2010
Related Publication 20120056171A1 · Mar 8, 2012