Condensed cyclic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10580997-B2
Application number	US-201715585829-A
Country	US
Kind code	B2
Filing date	May 3, 2017
Priority date	Jun 2, 2016
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

Abstract

A condensed cyclic compound represented by Formula 1:

wherein in Formula 1, a1, a2, Ar 1 , Ar 2 , R 1 , and R 2 are the same as described in the specification.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode as an anode;
a second electrode as a cathode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer,
wherein the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer,
wherein the hole transport region comprises an electron blocking layer, and
wherein the electron blocking layer comprises a condensed cyclic compound represented by Formula 1:

wherein, in Formula 1, Ar 1 is a group represented by Formulae 2A-1 to 2A-5, and Ar 2 is a group represented by Formula 2B,
ring A 1 in Formula 2B is a dibenzofuran ring or a dibenzothiophene ring,
R 1 to R 3 , R 11 , and R 12 in Formulae 1, 2A-1 to 2A-5, and 2B are each independently selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a pyridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group,
a1 in Formula 1 is an integer selected from 0 to 3, wherein, when a1 is two or more, two or more groups R 1 are identical to or different from each other,
a3 in Formulae 2A-1 to 2A-5 is an integer selected from 0 to 2, wherein when a3 is two or more, two or more groups R 3 are identical to or different from each other,
a2 and a12 in Formulae 1 and 2B are each independently an integer selected from 0 to 4, wherein, when a2 is two or more, two or more groups R 2 are identical to or different from each other, and when a12 is two or more, two or more groups R 12 are identical to or different from each other,
a11 in Formula 2B is an integer selected from 0 to 6, wherein, when a11 is two or more, two or more groups R 11 are identical to or different from each other,
R 4 , R 4a , and R 4b are each independently selected from:
a phenyl group, a biphenyl group, and a terphenyl group;
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group,
R 5 in Formulae 2A-1 to 2A-5 is selected from:
hydrogen, deuterium, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group; and
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium, and
* in Formulae 2A-1 to 2A-5 and 2B indicates a binding site to a neighboring atom.

2. The organic light-emitting device of claim 1 , wherein Ar 2 is one selected from groups represented by Formulae 2B-1 to 2B-6:

wherein, in Formulae 2B-1 to 2B-6,
X 1 is O or S,
R 12 and a12 are each independently the same as in claim 1 ,
R 13 to R 18 are each independently the same as R 11 in claim 1 , and
* indicates a binding site to a neighboring atom.

3. The organic light-emitting device of claim 1 , wherein R 1 to R 3 , R 11 , and R 12 are each independently selected from:
hydrogen, deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group;
a C 1 -C 10 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group.

4. The organic light-emitting device of claim 1 , wherein R 4 is one selected from groups represented by Formulae 3-1 to 3-7:

wherein, in Formulae 3-1 to 3-7,
R 21 to R 23 are each independently hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group,
a21 is an integer selected from 0 to 5,
a22 and a23 are each independently an integer selected from 0 to 4, and
* indicates a binding site to a neighboring atom.

5. The organic light-emitting device of claim 1 , wherein R 5 is hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group.

6. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound is represented by one selected from Formulae 1-1 to 1-4:

wherein, in Formulae 1-1 to 1-4, Ar 1 , A 2 , R 1 , R 2 , a1, and a2 are each independently the same as in claim 1 .

7. The organic light-emitting device of claim 6 ,
wherein, in Formulae 2A-1 to 2A-5,
R 4 , R 4a , and R 4b are each independently selected from groups represented by Formulae 3-1 to 3-7

wherein, in Formulae 3-1 to 3-7,
R 21 to R 23 are each independently hydrogen, deuterium, a C 1 -C 10 alkyl group, or a C 1 -C 10 alkoxy group,
a21 is an integer selected from 0 to 5,
a22 and a23 are each independently an integer selected from 0 to 4, and
* indicates a binding site to a neighboring atom.

8. The organic light-emitting device of claim 7 , wherein Ar 2 is one selected from groups represented by Formulae 2B-1 to 2B-6:

wherein, in Formulae 2B-1 to 2B-6,
X 1 is O or S,
R 12 and a12 are each independently the same as in claim 1 ,
R 13 to R 18 are each independently the same as R 11 in claim 1 , and
* indicates a binding site to a neighboring atom.

9. The organic light-emitting device of claim 8 , wherein R 12 to R 18 are each independently selected from:
hydrogen, deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group;
a C 1 -C 10 alkyl group and a C 1 -C 10 alkoxy group, each substituted with at least one deuterium; and
a phenyl group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, and a terphenyl group.

10. The organic light-emitting device of claim 1 , wherein the condensed cyclic compound has an absolute value of a highest occupied molecular orbital in a range of about 5.0 electron volts to about 5.3 electron volts.

11. The organic light-emitti

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Son Jhunmo
• Chae Miyoung
• Huh Dalho
• Kwon Eunsuk
• Kim Sangmo
• Kim Hyunjung
• Son Youngmok
• Lee Namheon
• LEE Saeyoun
• Jeon Soonok
• Chung Yeonsook
• Jung Yongsik

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title