Indenopyridine-based compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10134997-B2
Application number	US-201414457533-A
Country	US
Kind code	B2
Filing date	Aug 12, 2014
Priority date	Aug 30, 2013
Publication date	Nov 20, 2018
Grant date	Nov 20, 2018

Abstract

Provided are an indenopyridine-based compound and an organic light-emitting device including the same. The indenopyridine-based compound is represented by Formula 1:

First claim

What is claimed is:

1. An indenopyridine-based compound represented by Formula 1:

wherein, in Formula 1,
X 1 is a nitrogen atom (N) or C(R 11 ); X 2 is N or C(R 12 ); X 3 is N or C(R 13 ); X 4 is N or C(R 14 ); wherein only one of X 1 to X 4 is N;
L 1 is selected from:
i) an anthracenylene group, a chrysenylene group, and a pyrenylene group; and
ii) an anthracenylene group, a chrysenylene group, and a pyrenylene group, each substituted with at least one selected from:
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group;
a phenyl group, a naphthyl group, a pyridyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a pyridyl group, and a triazinyl group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group;
n1 is 1, 2, or 3;
R 1 and R 2 are each independently selected from a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted C 2 -C 30 heteroaryl group, wherein R 1 and R 2 are optionally connected to each other to form a substituted or unsubstituted C 6 -C 20 saturated ring or a substituted or unsubstituted C 6 -C 20 unsaturated ring;
R 11 to R 14 , R 3 , and R 4 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxyl group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, and a substituted or unsubstituted C 6 -C 30 arylthio group; and
a1 and a2 are each independently selected from an integer of 0, 1, 2 and 3.

2. The indenopyridine-based compound as claimed in claim 1 , wherein:
L 1 is selected from an anthracenylene group, a chrysenylene group, and a pyrenylene group.

3. The indenopyridine-based compound as claimed in claim 1 , wherein n1is an integer of 1 or 2.

4. The indenopyridine-based compound as claimed in claim 1 , wherein:
a moiety represented by (L 1 ) n1 is one selected from Formulae 3-1to 3-4:

wherein, in Formulae 3-1to 3-4,
* is a binding site with R 4 , and
** is a binding site with an indenopyridine ring portion of Formula 1.

5. The indenopyridine-based compound as claimed in claim 1 , wherein R 1 and R 2 are a phenyl group, or R 1 and R 2 combined are Formula 5:

wherein, in Formula 5,
* is a binding site with an indenopyridine ring.

6. The indenopyridine-based compound as claimed in claim 1 , wherein R 11 to R 14 , and R 3 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group.

7. The indenopyridine-based compound as claimed in claim 1 , wherein:
a2is 1, 2, or 3, and
R 4 is selected from:
i) a phenyl group, a naphthyl group, and an anthryl group; and
ii) a phenyl group, a naphthyl group, and an anthryl group, each substituted with at least one selected from a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, a tert-butyl group, a phenyl group, a naphthyl group, and an anthryl group.

8. The indenopyridine-based compound as claimed in claim 1 , wherein:
a2is 1, 2, or 3, and
R 4 is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

9. The indenopyridine-based compound as claimed in claim 1 , wherein a2 is an integer of 0 or 1.

10. The indenopyridine-based compound as claimed in claim 1 , wherein:
a2 is 1; and
a1 is 3.

11. The indenopyridine-based compound as claimed in claim 1 , wherein the indenopyridine-based compound is represented by Formula 1a:

wherein, in Formula 1a,
a moiety represented by (L 1 ) n1 is one selected from Formulae 3-1to 3-4:

wherein, in Formulae 3-1to 3-4,
* is a binding site with R 4 , and
** is a binding site with an indenopyridine ring portion of Formula 1a;

R 1 and R 2 are a phenyl group, or R 1 and R 2 combined are Formula 5:

wherein, in Formula 5,
* is a binding site with an indenopyridine ring;

R 3 and R 12 to R 14 are each independently selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group;
R 4 is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group;
a1 is 3; and
a2 is an integer of 0 or 1.

12. The indenopyridine-based compound as claimed in claim 1 , wherein the indenopyridine-based compound is represented by one of Formulae 1b to 1e:

wherein, in Formulae 1b to 1e,
a moiety represented by (L 1 ) n1 is one selected from Formulae 3-1to 3-4:

wherein, in Formulae 3-1to 3-4,
* is a binding site with R 4 , and
** is a binding site with an indenopyridine ring portion of Formulae 1b to 1e;

R 1 and R 2 are a phenyl group, or R 1 and R 2 combined are Formula 5:

wherein, in Formula 5,
* is a binding site with an indenopyridine ring;

R 13 is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a nitro group, and a methyl group;
R 4 is selected from a phenyl group, a 1-naphthyl group, and a 2-naphthyl group; and
a2is an integer of 0 or 1.

13. The indenopyridine-based compound as claimed in claim 1 , wherein the indenopyridine-based compound represented by Formula 1 is one selected from Compounds 1, 3, 5, 7 to 9, 11 to 13, 15, 16, and 20 to 25:

Assignees

• Samsung Display Co Ltd
• Sungkyunkwan Univ Foundation For Corporate Collaboration

Inventors

• Kim Soung-Wook
• Kim Myeong-Suk
• Kim Jae-Hong
• Kho Sam-Il
• Yoon Seung-Soo

Classifications

• H01L51/006

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• C07D221/16 Primary

  containing carbocyclic rings other than six-membered · CPC title

• H01L51/5012

  Electricity · mapped topic

• H01L51/0052 Primary

  Electricity · mapped topic