Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode

Patent metadata

Field	Value
Publication number	US-10522761-B2
Application number	US-201514626410-A
Country	US
Kind code	B2
Filing date	Feb 19, 2015
Priority date	Aug 21, 2012
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

The compound for an organic optoelectronic device provides an organic light emitting diode having life-span characteristics due to excellent electrochemical and thermal stability, and having high luminous efficiency at a low driving voltage.

First claim

What is claimed is:

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

wherein, in Chemical Formula 1,
X is nitrogen (N),
X 1 is —O—, —S—, —CR′R″—, or —SiR′R″—, wherein R′ and R″ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C18 aryl group,
X 2 is —O— or —S—,
L 1 , L 2 , and L 3 are each an unsubstituted phenyl group,
Ar 1 and Ar 2 are each independently substituted or unsubstituted C6 to C30 aryl group,
R 1 is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
R 2 and R 3 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C18 heteroaryl group,
n1 is 1, and
n2 and n3 are each independently 0 or 1.

2. The compound for an organic optoelectronic device as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted fluorenyl group.

3. The compound for an organic optoelectronic device as claimed in claim 1 , wherein the compound represented by Chemical Formula 1 is represented by one of the following Chemical Formulae A-132, B-56, C-113, C-127, C-143, C-144, C-160, C-206, C-236, or C-243:

4. The compound for an organic optoelectronic device as claimed in claim 1 , wherein the organic optoelectronic device is an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic transistor, an organic photo-conductor drum, or an organic memory device.

5. An organic light emitting diode, comprising:
an anode, a cathode, and at least one organic thin layer interposed between the anode and cathode,
wherein the at least one organic thin layer includes the compound for an organic optoelectronic device as claimed in claim 1 .

6. The organic light emitting diode as claimed in claim 5 , wherein the at least one organic thin layer includes an emission layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, or a combination thereof.

7. The organic light emitting diode as claimed in claim 5 , wherein the compound for an organic optoelectronic device is included in a hole transport layer, a hole injection layer, or an emission layer.

8. The organic light emitting diode as claimed in claim 7 , wherein:
the at least one organic thin layer includes the emission layer, and
the compound for an organic optoelectronic device is a phosphorescent host material or fluorescent host material in the emission layer.

9. A compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 2:

wherein, in Chemical Formula 2,
X is boron (B), nitrogen (N), or phosphorus (P),
X 1 to X 4 are each independently —O—, —S—, —S(O 2 )—, —CR′R″—, —SiR′R″—, or —GeR′R″—, wherein R′ and R″ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and at least one of X 1 or X 3 is —CR′R″—, —SiR′R″—, or —GeR′R″—,
L 1 to L 3 are each independently a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
Ar 1 is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group,
R 1 and R 4 to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
R 2 and R 3 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C18 heteroaryl group, and
n1 to n3 are each independently an integer of 0 to 3.

10. The compound for an organic optoelectronic device as claimed in claim 9 , wherein Ar 1 is a substituted or unsubstituted C6 to C30 aryl group.

11. The compound for an organic optoelectronic device as claimed in claim 9 , wherein Ar 1 is a substituted or unsubstituted C2 to C30 heteroaryl group.

12. A compound for an organic optoelectronic device, the compound being represented by the following Chemical Formula 3:

wherein, in Chemical Formula 3,
X is boron (B), nitrogen (N), or phosphorus (P),
X 1 to X 5 are each independently —O—, —S—, —S(O 2 )—, —CR′R″—, —SiR′R″—, or —GeR′R″—,
X 6 is a single bond, —O—, —S—, —S(O 2 )—, —CR′R″—, —SiR′R″—, or —GeR′R″—, wherein R′ and R″ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C 10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and at least one of X 1 , X 3 , and X 5 is —CR′R″—, —SiR′R″—, or —GeR′R″—,
L 1 to L 3 are each independently a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C2 to C10 alkynylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
R 1 and R 4 to R 9 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
R 2 and R 3 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C18 heteroaryl group, and
n1 to n3 are each independently an integer of 0 to 3.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Ryu Dong-Wan
• Kang Eui-Su
• Lee Han-Ill
• Jung Sung-Hyun
• Jo Young-Kyoung
• Chae Mi-Young
• Huh Dal-Ho
• Hong Jin-Seok

Classifications

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D335/12

  Thioxanthenes · CPC title

• C07D311/82 Primary

  Xanthenes · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title