IP Library Granted Patent US 8,247,805
Granted Patent B2
US 8,247,805 · App. 12/588,365 · Granted Aug 21, 2012

Material for organic photoelectric device including electron transporting unit and hole transporting unit, and organic photoelectric device including the same

Assignee: Cheil Industries, Inc.
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Quick Facts
Patent No.
US 8,247,805
App. No.
12/588,365
Granted
Aug 21, 2012
Kind
B2
Abstract

A material for an organic photoelectric device, the material including a compound including a pyridine moiety, the compound being a bipolar organic compound including both a hole transporting unit and an electron transporting unit, the compound being represented by the following Formula 1:

Claims (57)

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

a compound including a pyridine

moiety, the compound being a bipolar organic compound including both a hole transporting unit and an electron transporting unit, the compound being represented by the following Formula 1:

wherein, in Formula 1:

the pyridine moiety is an electron transporting unit,

the HTU and HTU′ independently function as a hole transporting unit, and

the HTU and HTU′ are the same or different; and

a dopant, wherein the compound represented by Formula 1 is a host, and the dopant is a phosphorescent or fluorescent dopant selected from the group consisting of red, green, blue, and white phosphorescent or fluorescent dopants, and combinations thereof.

2. The material as claimed in claim 1 , wherein the compound represented by Formula 1 is further represented by the following Formula 2:

wherein, in Formula 2:

X and Y are independently selected from the group consisting of nitrogen (N), sulfur (S), and oxygen (O),

Ar 1 and Ar 2 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene,

R 1 to R 4 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene, or R 1 and R 2 form a cyclic ring or R 3 and R 4 form a cyclic ring,

when X is sulfur or oxygen, R 2 is a unshared electron pair, and when Y is sulfur or oxygen, R 4 is a unshared electron pair, and

m and n are independently integers ranging from 0 to 3, m+n is more than or equal to 1, and o and p are integers ranging from 0 to 2.

3. The material as claimed in claim 2 , wherein at least one of the groups XR 1 R 2 and YR 3 R 4 in Formula 2 is represented by the following Formula 6a:

wherein, in Formula 6a:

Ar 16 and Ar 17 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl and a substituted or unsubstituted C2 to C30 heteroaryl.

4. The material as claimed in claim 2 , wherein at least one of the groups XR 1 R 2 and YR 3 R 4 in Formula 2 is represented by the following Formula 6b:

wherein, in Formula 6b:

R 9 and R 10 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiR 15 R 16 R 17 (where R 15 to R 17 are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and

s 1 and s 2 are independently integers ranging from 0 to 4.

5. The material as claimed in claim 2 , wherein at least one of the groups XR 1 R 2 and YR 3 R 4 in Formula 2 is represented by the following Formula 6c:

wherein, in Formula 6c:

R 11 and R 12 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiR 15 R 16 R 17 (where R 15 to R 17 are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and

s 3 and s 4 are independently integers ranging from 0 to 4.

6. The material as claimed in claim 2 , wherein at least one of the groups XR 1 R 2 and YR 3 R 4 in Formula 2 is represented by the following Formula 6d:

wherein, in Formula 6d:

R 13 and R 14 are independently substituents selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C2 to C20 alkoxy, and SiR 15 R 16 R 17 (where R 15 to R 17 are independently selected from the group consisting of a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C3 to C30 cycloalkyl, a nitrile, a cyano, a nitro, a carbonyl, and an amide), and

s 5 and s 6 are independently integers ranging from 0 to 4.

7. The material as claimed in claim 2 , wherein the compound represented by Formula 2 is selected from the group consisting of the following Compounds (1) to (41), and combinations thereof:

8. The material as claimed in claim 1 , wherein the compound represented by Formula 1 is further represented by the following Formula 3:

wherein, in Formula 3:

Ar 3 and Ar 4 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene,

R 5 to R 8 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C2 to C30 heteroarylene, a substituted or unsubstituted C1 to C30 alkyl, and a substituted or unsubstituted C1 to C30 alkylene, or R 5 and R 6 form a cyclic ring or R 7 and R 8 form a cyclic ring, and

m and n are independently integers ranging from 0 to 3, and m+n is more than or equal to 1.

9. The material as claimed in claim 1 , wherein the compound represented by Formula 1 is further represented by the following Formula 4:

wherein, in Formula 4:

Ar 5 to Ar 10 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene, or Ar 5 and Ar 6 form a cyclic ring, Ar 7 and Ar 8 form a cyclic ring, or Ar 9 and Ar 10 form a cyclic ring, and

q is an integer ranging from 0 to 2.

10. The material as claimed in claim 1 , wherein the compound represented by Formula 1 is further represented by the following Formula 5:

wherein, in Formula 5:

Ar 11 to Ar 15 are independently selected from the group consisting of a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C6 to C30 arylene, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C30 alkylene, a substituted or unsubstituted C2 to C30 heteroaryl, and a substituted or unsubstituted C2 to C30 heteroarylene, or Ar 12 and Ar 13 form a cyclic ring, or Ar 14 and Ar 15 form a cyclic ring, and

r is an integer ranging from 0 to 2.

11. The material as claimed in claim 10 , wherein the compound represented by Formula 5 is selected from the group consisting of the following Compounds (42) to (52), and combinations thereof:

12. The material as claimed in claim 1 ,

wherein the dopant is a phosphorescent dopant.

13. The material as claimed in claim 1 ,

wherein the dopant is a fluorescent dopant.

14. An organic photoelectric device, comprising

an anode;

a cathode; and

an organic thin layer disposed between the anode and cathode,

wherein the organic thin layer comprises the material as claimed in claim 1 .

15. The organic photoelectric device of claim 14 , wherein the organic thin layer comprises:

an emission layer; and

at least one layer selected from the group consisting of a hole transport layer (HTL), a hole injection layer (HIL), an electron transport layer (ETL), an electron injection layer (EIL), and combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 4, 2010
From: YU, EUN-SUN; KIM, NAM-SOO; KIM, YOUNG-HOON; CHAE, MI-YOUNG; KANG, EUI-SU
To: CHEIL INDUSTRIES, INC.
Reel/Frame 023958/0843 →
Priority Claims (1)
KR 10-2007-0036407 · Apr 13, 2007 · national
Continuity (2)
Continuation PCTKR2008002098 · Apr 14, 2008
Related Publication 20100155706A1 · Jun 24, 2010