Compound and organic light-emitting diode including the same

Patent metadata

Field	Value
Publication number	US-9397300-B2
Application number	US-201313924467-A
Country	US
Kind code	B2
Filing date	Jun 21, 2013
Priority date	Feb 14, 2013
Publication date	Jul 19, 2016
Grant date	Jul 19, 2016

Abstract

Provided is an organic light-emitting diode including a compound of Formula 1 below:

A detailed description of a substituent in Formula 1 above is defined as described in the detailed description.

First claim

What is claimed is:

1. A compound represented by Formula 1 below:

wherein, in Formula 1,
R 1 and R 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group;
Ar 1 is a C 6 -C 60 aryl group substituted with CN or F, a substituted or unsubstituted C 2 -C 60 heteroaryl group (excluding a substituted or unsubstituted pyridyl group and a substituted or unsubstituted isoquinolyl group), or a substituted C 6 -C 60 condensed polycyclic group;
Ar 2 is a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group (excluding a substituted or unsubstituted pyridyl group), or a substituted or unsubstituted C 6 -C 60 condensed polycyclic group; and
X is a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl group, a substituted or unsubstituted C 6 -C 60 condensed polycyclic group, or a divalent linking group with at least two of the aryl group, the heteroaryl group, and the condensed polycyclic group linked together.

2. The compound of claim 1 , wherein R 1 and R 2 are identical to each other.

3. The compound of claim 1 , wherein R 1 and R 2 are each independently one of the following compounds represented by Formulas 2a to 2f below:

wherein, in Formulas 2a to 2e,
Q 1 is a linking group represented by —C(R 30 )(R 31 )— or —N(R 32 )—;
Z 1 , R 30 , R 31 , and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano atom, a nitro group, a hydroxyl group, or a carboxyl group;
p is an integer from 1 to 9; and
* is a binding site.

4. The compound of claim 1 , wherein Ar 2 is a linking group with at least one of the following groups represented by Formulas 3a to 3e below:

wherein, in Formulas 3a to 3e,
Y 1 and Y 2 are each independently a linking group represented by —N═ or —C(R 21 )═;
Q 2 is a linking group represented by —C(R 30 )(R 31 )—, —N(R 32 )—, —S—, or —O—;
Z 1 , Z 2 , R 21 , R 30 , R 31 , and R 32 are each independently a hydrogen group, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group; and
* is a binding site.

5. The compound of claim 1 , wherein X in Formula 1 is one of the following compounds represented by Formulas 4a to 4d below:

wherein, in Formulas 4a to 4d,
Q 3 is a linking group represented by —C(R 30 )(R 31 )— or —S—;
R 30 and R 31 are each independently a hydrogen group, a deuterium atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 20 condensed polycyclic group, a halogen atom, a cyano group, a nitro group, a hydroxyl group, or a carboxyl group; and
* is a binding site.

6. A compound represented by one of the following structures

7. An organic light-emitting diode (OLED) comprising:
a first electrode;
a second electrode; and
an organic layer that is disposed between the first electrode and the second electrode, and includes the compound of claim 1 .

8. The OLED of claim 7 , wherein the organic layer is an emission layer, and the compound is used as a fluorescent host, a phosphorescent host, or a fluorescent dopant.

9. The OLED of claim 7 , wherein the organic layer includes an electron injection layer, an electron transport layer, or a functional layer having both electron injection and electron transport capabilities.

10. The OLED of claim 7 , wherein the organic layer is a blue emission layer.

11. The OLED of claim 7 , wherein the organic layer is a blue layer, and the compound of Formula 1 is used as a blue fluorescent host or a dopant.

12. The OLED of claim 7 comprising an emission layer, an electron injection layer, an electron transport layer, a functional layer having both electron injection and electron transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport capabilities,
wherein the emission layer, the electron injection layer, the electron transport layer, or the functional layer having both electron injection and electron transport capabilities comprises the compound of claim 1 , and
the emission layer further comprises an anthracene-based compound, an arylamine-based compound, or a styryl-based compound.

13. The OLED of claim 7 comprising an emission layer, an electron injection layer, an electron transport layer, a functional layer having both electron injection and electron transport capabilities, a hole injection layer, a hole transport layer, or a functional layer having both hole injection and hole transport capabilities,
wherein the electron injection layer, the electron transport layer, or the functional layer having both electron injection and electron transport capabilities comprises a compound represented by Formula 1,
wherein at least one of a red emission layer, a green emission layer, a blue emission layer, and a white emission layer of the emission layer comprises a phosphorescent compound.

14. The OLED of claim 13 , wherein the hole injection layer, the hole transport layer, or the functional layer having both hole injection and hole transport capabilities comprises a charge-generating material.

15. The OLED of claim 14 , wherein the charge-generating material is a p-dopant.

16. The OLED of claim 15 , wherein the p-dopant is a quinone derivative, a metal oxide, or a cyano group-containing compound.

17. The OLED of claim 7 , wherein the organic layer comprises an electron transport layer, and the electron transport layer further comprises a metal complex.

18. The OLED of claim 17 , wherein the metal complex is a lithium (Li) complex.

19.

Assignees

• Samsung Display Co Ltd

Inventors

• Park Jun-Ha
• Hwang Seok-Hwan
• Kim Young-Kook
• Jung Hye-Jin
• Lee Eun-Young
• Lim Jin-O
• Han Sang-Hyun
• Jeong Eun-Jae
• Kim Soo-Yon
• Lee Jong-Hyuk

Classifications

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C07D251/22

  to two ring carbon atoms · CPC title

• C07C211/56

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07D215/38

  Nitrogen atoms (nitro radicals C07D215/18) · CPC title

• C07D235/18

  with aryl radicals directly attached in position 2 · CPC title