Condensed cyclic compound and organic electroluminescence device including the same

Patent metadata

Field	Value
Publication number	US-12538702-B2
Application number	US-201715840986-A
Country	US
Kind code	B2
Filing date	Dec 13, 2017
Priority date	Dec 13, 2016
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

A condensed cyclic compound which improves emission life and efficiency and an organic electroluminescence device is provided. The condensed cyclic compound according to the inventive concept is represented by the following

where each of X, Y and Z is independently a substituted or unsubstituted pentagonal hydrocarbon ring, a substituted or unsubstituted hexagonal hydrocarbon ring, a substituted or unsubstituted pentagonal heterocycle, or a substituted or unsubstituted hexagonal heterocycle, the pentagonal heterocycle and the hexagonal heterocycle each independently includes one heteroatom, each of a and b is independently 0 or 1, and Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring.

First claim

What is claimed is:

1 . A condensed cyclic compound represented by the following Formula 1:

where X and Z are each independently a substituted or unsubstituted pentagonal hydrocarbon ring, a substituted or unsubstituted hexagonal hydrocarbon ring, a substituted or unsubstituted pentagonal heterocycle, or a substituted or unsubstituted hexagonal heterocycle,
Y is a substituted or unsubstituted pentagonal heterocycle,
the pentagonal heterocycle and the hexagonal heterocycle each independently includes one heteroatom,
a and b are each independently 0 or 1,
Y is not a pentagonal heterocycle with an N,
a quinolinyl group or

is bonded to X if Y is a pentagonal heterocycle with an oxygen atom or a sulfur atom, and
Ar 1 is an unsubstituted phenyl group.

2 . The condensed cyclic compound of claim 1 , wherein Formula 1 is represented by the following Formula 2:

where A is O or S,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl having 3 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms for forming a ring,
R 1 is a quinolinyl group or

if A is O or S,
m is an integer of 1 to 4,
n is an integer of 0 to 4, and
a, b, and Ar 1 are the same as defined in formula 1.

3 . The condensed cyclic compound of claim 2 , wherein Formula 2 is represented by the following Formula 3:

where A, R 1 , R 2 , m, n and Ar 1 are the same as defined in Formula 2.

4 . The condensed cyclic compound of claim 2 , wherein Formula 2 is represented by the following Formula 4:

where R 1 , R 2 , m, n and Ar 1 are the same as defined in Formula 2.

5 . The condensed cyclic compound of claim 4 , wherein Formula 4 is represented by the following Formula 4-1 or Formula 4-2:

where R 1 , R 2 , m, n and Ar 1 are the same as defined in Formula 2.

6 . The condensed cyclic compound of claim 3 , wherein the condensed cyclic compound represented by Formula 3 is one selected from compounds represented in the following Compound Group 1:

7 . The condensed cyclic compound of claim 4 , wherein the condensed cyclic compound represented by Formula 4 is one selected from compounds represented in the following Compound Group 3:

8 . An organic electroluminescence device, comprising:
a first electrode; a hole transport region disposed on the first electrode; an emission layer disposed on the hole transport region; an electron transport region disposed on the emission layer; and a second electrode disposed on the electron transport region, wherein the electron transport region comprises a condensed cyclic compound represented by the following Formula 1:

where X and Z are each independently a substituted or unsubstituted pentagonal hydrocarbon ring, a substituted or unsubstituted hexagonal hydrocarbon ring, a substituted or unsubstituted pentagonal heterocycle, or a substituted or unsubstituted hexagonal heterocycle,
Y is a substituted or unsubstituted pentagonal heterocycle,
the pentagonal heterocycle and the hexagonal heterocycle each independently includes one heteroatom,
a and b are each independently 0 or 1,
Y is not a pentagonal heterocycle with an N,
a quinolinyl group or

is bonded to X if Y is a pentagonal heterocycle with an oxygen atom or a sulfur atom, and
Ar 1 is an unsubstituted phenyl group.

9 . The organic electroluminescence device of claim 8 , wherein Formula 1 is represented by the following Formula 3:

where A is O or S,
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms for forming a ring,
m is an integer of 1 to 4,
n is an integer of 0 to 4,
R 1 is a quinolinyl group or

if A is O or S, and
Ar 1 is the same as defined in Formula 1.

10 . The organic electroluminescence device of claim 8 , wherein Formula 1 is represented by the following Formula 4:

where R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms for forming a ring, or a substituted or unsubstituted condensed polycyclic group having 6 to 60 carbon atoms for forming a ring,
m and n are each independently an integer of 0 to 4, and
Ar 1 is the same as defined in Formula 1.

11 . The organic electroluminescence device of claim 8 , wherein the hole transport region comprises an amine compound represented by the following Formula 6:

where Ar 2 is a substituted or unsubstituted aryl group

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junha
• Sim Mun-Ki
• Lee Hyoyoung
• Jeong Eunjae
• Kim Youngkook
• Hwang Seokhwan

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K50/12

  comprising dopants · CPC title