IP Library Granted Patent US 9,595,677
Granted Patent B2
US 9,595,677 · App. 13/677,619 · Granted Mar 14, 2017

Material for organic photoelectric device, and organic photoelectric device including the same

Inventors: Nam-Soo Kim (Uiwang-si, KR); Eun-Sun Yu (Uiwang-si, KR); Young-Hoon Kim (Uiwang-si, KR); Mi-Young Chae (Uiwang-si, KR)
Assignee: Cheil Industries, Inc.
H01L51/005C07D403/14C09B1/00C09B57/00C09K11/06H01L51/0067H01L51/0072H01L51/5016
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Quick Facts
Patent No.
US 9,595,677
App. No.
13/677,619
Granted
Mar 14, 2017
Kind
B2
Abstract

A material for an organic photoelectric device includes a compound represented by the following Formula 1:

Claims (85)

1. A material for an organic photoelectric device, the material comprising:

a compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C1 to C30 alkyl or alkylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 1 and R 6 are independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, or a substituted or unsubstituted C1 to C30 alkyl,

R 2 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 2 and R 3 are joined together to form a ring,

R 4 and R 5 are joined together to form a ring,

m and n are integers ranging from 0 to 3, and m+n is an integer ranging from 1 to 6,

o and p are integers ranging from 0 to 2, and o+p is an integer ranging from 1 to 4, and

at least one of R 2 to R 5 is substituted with a C2 to C30 heteroaryl.

2. The material as claimed in claim 1 , wherein:

m is an integer ranging from 1 to 3,

at least one of R 2 or R 3 is substituted with the C2 to C30 heteroaryl, and

n satisfies one of the following conditions:

n is an integer ranging from 1 to 3 and R 4 and R 5 are unsubstituted, or

n is 0.

3. The material as claimed in claim 1 , wherein:

n is an integer ranging from 1 to 3,

at least one of R 4 or R 5 is substituted with the C2 to C30 heteroaryl, and

m satisfies one of the following conditions:

m is an integer ranging from 1 to 3 and R 2 and R 3 are unsubstituted or

m is 0.

4. The material as claimed in claim 1 , wherein the compound represented by Formula 1 has a glass transition temperature of about 120° C. or more and has a thermal decomposition temperature of about 400° C. or more.

5. An organic photoelectric device, comprising:

an anode, a cathode, and an organic layer disposed between the anode and cathode,

wherein the organic layer includes a compound represented by the following Formula 1:

wherein, in Formula 1,

AR 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C1 to C30 alkyl or alkylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 1 and R 6 are independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, or a substituted or unsubstituted C1 to C30 alkyl,

R 2 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene, or a substituted or unsubstituted C1 to C30 alkyl or alkylene,

R 2 and R 3 are joined together to form a ring,

R 4 and R 5 are joined together to form a ring,

m and n are integers ranging from 0 to 3, and m+n is an integer ranging from 1 to 6,

o and p are integers ranging from 0 to 2, and o+p is an integer ranging from 1 to 4, and

at least one of R 2 to R 5 is substituted with a C2 to C30 heteroaryl.

6. The organic photoelectric device as claimed in claim 5 , wherein the organic layer is an emission layer.

7. The organic photoelectric device as claimed in claim 6 , wherein the compound represented by Formula 1 is present as a phosphorescent or fluorescent host of the emission layer.

8. The organic photoelectric device as claimed in claim 7 , further comprising a phosphorescent or fluorescent dopant combined with the host, the dopant being a red, green, blue, or white light emitting dopant.

9. The organic photoelectric device as claimed in claim 6 , wherein the compound represented by Formula 1 is a fluorescent blue dopant in the emission layer.

10. The organic photoelectric device as claimed in claim 5 , wherein the organic layer is an electron transport layer (ETL), an electron injection layer (EIL), or a combination thereof.

11. The organic photoelectric device as claimed in claim 5 , wherein the organic layer is a hole transport layer (HTL), a hole injection layer (HIL), or a combination thereof.

12. The organic photoelectric device as claimed in claim 5 , wherein the organic layer is an emission layer, a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), or a combination thereof.

13. A material for an organic photoelectric device, the material comprising:

a compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C1 to C30 alkyl or alkylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene, provided that at least one of Ar 1 and Ar 2 is a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 1 and R 6 are independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, or a substituted or unsubstituted C1 to C30 alkyl,

R 2 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene, or a substituted or unsubstituted C1 to C30 alkyl or alkylene,

R 2 and R 3 are joined together to form a ring,

R 4 and R 5 are joined together to form a ring,

m and n are integers ranging from 0 to 3, and m+n is an integer ranging from 1 to 6, and

o and p are integers ranging from 0 to 2, and o+p is an integer ranging from 1 to 4.

14. The material as claimed in claim 13 , wherein:

m is an integer ranging from 1 to 3 and o is an integer ranging from 1 to 2, or

n is an integer ranging from 1 to 3 and p is an integer ranging from 1 to 2.

15. An organic photoelectric device, comprising:

an anode, a cathode, and an organic layer disposed between the anode and cathode,

wherein the organic layer includes a material that includes:

a compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C1 to C30 alkyl or alkylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 1 and R 6 are independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or a substituted or unsubstituted C1 to C30 alkyl,

R 2 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene, or a substituted or unsubstituted C1 to C30 alkyl or alkylene,

R 2 and R 3 are joined together to form a ring,

R 4 and R 5 are joined together to form a ring,

m and n are integers ranging from 0 to 3, and m+n is an integer ranging from 1 to 6,

o and p are integers ranging from 0 to 2, and o+p is an integer ranging from 1 to 4, and

at least one of R 2 to R 5 is substituted with a C2 to C30 heteroaryl.

16. A material for an organic photoelectric device, the material comprising:

a compound represented by the following Formula 1:

wherein, in Formula 1,

Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, a substituted or unsubstituted C1 to C30 alkyl or alkylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 1 and R 6 are independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or a substituted or unsubstituted C1 to C30 alkyl,

R 2 to R 5 are independently a substituted or unsubstituted C6 to C30 aryl or arylene, or a substituted or unsubstituted C2 to C30 heteroaryl or heteroarylene,

R 2 and R 3 are joined together to form a ring,

R 4 and R 5 are joined together to form a ring,

m and n are integers ranging from 0 to 3, and m+n is an integer ranging from 1 to 6,

o and p are integers ranging from 0 to 2, and o+p is an integer ranging from 1 to 4, and

at least one of R 2 to R 5 is substituted with a C2 to C30 heteroaryl, and

wherein one of the following conditions is satisfied:

m is an integer ranging from 1 to 3, at least one of R 2 or R 3 is substituted with the C2 to C30 heteroaryl, n is an integer ranging from 1 to 3, and R 4 and R 5 are unsubstituted,

m is an integer ranging from 1 to 3, at least one of R 2 or R 3 is substituted with the C2 to C30 heteroaryl, and n is 0,

n is an integer ranging from 1 to 3, at least one of R 4 or R 5 is substituted with the C2 to C30 heteroaryl, m is an integer ranging from 1 to 3 and R 2 and R 3 are unsubstituted, or

n is an integer ranging from 1 to 3, at least one of R 2 or R 3 is substituted with the C2 to C30 heteroaryl, and m is 0.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2012
From: KIM, NAM-SOO; YU, EUN-SUN; KIM (LEGAL REPRESENTATIVE), JA-HYUN; KIM (DECEASED), YOUNG-HOON; CHAE, MI-YOUNG
To: CHEIL INDUSTRIES, INC.
Reel/Frame 029311/0678 →
Priority Claims (1)
KR 10-2007-0090015 · Sep 5, 2007 · national
Continuity (3)
Continuation 12659356 · Mar 5, 2010
Continuation PCTKR2008005263 · Sep 5, 2008
Related Publication 20130099214A1 · Apr 25, 2013