Benzimidazole compound, organic photoelectric device including the same, and display element including the same

Patent metadata

Field	Value
Publication number	US-9530970-B2
Application number	US-201313892604-A
Country	US
Kind code	B2
Filing date	May 13, 2013
Priority date	Oct 14, 2008
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

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

First claim

What is claimed is:

1. A benzimidazole compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
A is CR″ or N wherein R″ is hydrogen or a C1 to C10 alkyl,
Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene,
x and y are each independently an integer of 1 to 5, provided that 2≦x+y≦5,
R is hydrogen or a C1 to C7 alkyl,
n is an integer of 0 to 3,
R′ is one selected from the group of a substituted or unsubstituted C1 to C50 alkyl and a substituted or unsubstituted C6 to C50 aryl, and
m is 1 or 2.

2. The benzimidazole compound as claimed in claim 1 , wherein R′ in Chemical Formula 1 is a substituted or unsubstituted C6 to C50 aryl.

3. The benzimidazole compound as claimed in claim 1 , wherein the benzimidazole compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2:

wherein, in Chemical Formula 2,
A is CR″ or N wherein R″ is hydrogen or a C1 to C10 alkyl,
Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 arylamine, a substituted or unsubstituted C2 to C30 heteroarylamine, a substituted or unsubstituted carbazole, and a substituted or unsubstituted fluorene,
x and y are each independently integers of 1 to 5, provided that 2≦x+y≦5,
n is an integer of 0 to 3,
R 1 ′ to R 5 ′ are each independently one selected from the group of hydrogen, a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20 acyloxy, a substituted or unsubstituted C2 to C20 heteroaryloxy, a substituted or unsubstituted C7 to C20 aryloxycarbonyl amino, a substituted or unsubstituted C1 to C20 sulfamoyl amino, a substituted or unsubstituted C1 to C20 sulfonyl, a substituted or unsubstituted C1 to C20 alkylthiol, a substituted or unsubstituted C6 to C20 arylthiol, a substituted or unsubstituted C1 to C20 heterocyclothiol, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C1 to C20 phosphoric acid amide, and a substituted or unsubstituted C3 to C40 silyl, and
m is 1 or 2.

4. The benzimidazole compound as claimed in claim 1 , wherein Ar 1 to Ar 2 are each independently one selected from the group of a substituted or unsubstituted C6 to C30 arylamine and a substituted or unsubstituted carbazole.

5. The benzimidazole compound as claimed in claim 1 , wherein:
one of Ar 1 and Ar 2 includes a substituted or unsubstituted C6 to C30 arylamine, and
another of Ar 1 and Ar 2 includes a substituted or unsubstituted carbazole.

6. The benzimidazole compound as claimed in claim 1 , wherein Ar 1 to Ar 2 are each independently represented by one of the following Chemical Formulae 7, 24, 28, and 33:

wherein, in Chemical Formulae 7, 24, 28, and 33,
R 8 , R 9 , R 44 , R 45 , R 55 to R 58 , and R 72 to R 74 are each independently one selected from the group of a halogen, a cyano, a hydroxy, an amino, a nitro, a carboxyl, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C1 to C20 alkenyl, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, a substituted or unsubstituted C1 to C20 alkoxy, a substituted or unsubstituted C6 to C20 aryloxy, a substituted or unsubstituted C3 to C40 silyloxy, a substituted or unsubstituted C1 to C20 acyl, a substituted or unsubstituted C2 to C20 alkoxycarbonyl, a substituted or unsubstituted C2 to C20 acyloxy, a substituted or unsubstituted C2 to C20 heteroaryloxy, a substituted or unsubstituted C7 to C20 aryloxycarbonyl amino, a substituted or unsubstituted C1 to C20 sulfamoyl amino, a substituted or unsubstituted C1 to C20 sulfonyl, a substituted or unsubstituted C1 to C20 alkylthiol, a substituted or unsubstituted C6 to C20 arylthiol, a substituted or unsubstituted C1 to C20 heterocyclothiol, a substituted or unsubstituted C1 to C20 ureide, a substituted or unsubstituted C1 to C20 phosphoric acid amide, and a substituted or unsubstituted C3 to C40 silyl,
n 8 , n 44 , n 55 , n 57 , n 72 , and n 73 are each independently integers of 0 to 4,
n 9 , n 45 , n 56 , and n 58 are each independently integers of 0 to 3.

7. The benzimidazole compound as claimed in claim 1 , wherein the benzimidazole compound is a charge transporting material or a host material in an organic photoelectric device.

8. The benzimidazole compound as claimed in claim 1 , wherein the benzimidazole compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulae 36 and 40:

9. An organic photoelectric device, comprising:
an anode,
a cathode, and
at least one organic thin layer between the anode and cathode, the at least one organic thin layer including the benzimidazole compound as claimed in claim 1 .

10. The organic photoelectric device as claimed in claim 9 , wherein the at least one organic thin layer is an emission layer.

11. The organic photoelectric device as claimed in claim 9 , wherein the at least one organic thin layer includes one or more of an electron injection layer (EIL), an electron transport layer (ETL), or a hole blocking layer.

12. A display element comprising the organic photoelectric device as claimed in claim 9 .

Assignees

• Jung Sung-Hyun
• Kim Hyung-Sun
• Kim Young-Hoon
• Lee Ho-Jae
• Lee Seung-Gyoung
• Yu Eun-Sun
• Chae Mi-Young
• Cheil Ind Inc

Inventors

• Jung Sung-Hyun
• Kim Hyung-Sun
• Kim Young-Hoon
• Lee Ho-Jae
• Lee Seung-Gyoung
• Yu Eun-Sun
• Chae Mi-Young

Classifications

• H01L51/0081

  Electricity · mapped topic

• C09K2211/1466

  containing nitrogen as the only heteroatom · CPC title

• H01L51/0037

  Electricity · mapped topic

• H01L51/0003

  Electricity · mapped topic

• C07D403/14

  containing three or more hetero rings · CPC title