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

Patent metadata

Field	Value
Publication number	US-11508914-B2
Application number	US-201816206331-A
Country	US
Kind code	B2
Filing date	Nov 30, 2018
Priority date	Oct 5, 2015
Publication date	Nov 22, 2022
Grant date	Nov 22, 2022

Abstract

A condensed cyclic compound represented by Formula 1:

wherein in Formula 1, Ar 1 and R 1 to R 8 are the same as described in the specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein Ar 1 in Formula 1 is selected from a group represented by Formula 2A-4,

wherein, in Formula 2A-4,
X 4 is C(R 37 )(R 38 ), or Si(R 37 )(R 38 ),
wherein
R 3 to R 8 , R 11 to R 15 , R 17 , R 22 , R 24 R 25 , R 37 and R 38 in Formulae 1 and 2A-4 are each independently:
hydrogen, deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl 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 selected from deuterium and a cyano group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and a dibenzosilolyl group, each substituted with at least one of deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and a dibenzosilolyl group;
R 1 and R 2 in Formula 1 and R 23 in Formula 2A-4 are each independently:
hydrogen, deuterium, a cyano group, a C 1 -C 20 alkoxy group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl 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 selected from deuterium and a cyano group; and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and a dibenzosilolyl group, each substituted with at least one of deuterium, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, and a dibenzosilolyl group;
wherein at least one of R 1 and R 2 in Formula 1 is a cyano group,
and
* indicates a binding site to an adjacent atom.

2. The condensed cyclic compound of claim 1 , wherein
R 1 to R 8 , R 11 to R 15 , R 17 , R 22 to R 25 , R 37 and R 38 are each independently selected from
hydrogen, deuterium, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group;
a C 1 -C 20 alkyl group substituted with at least one of deuterium and a cyano group; and
a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, and a dibenzosilolyl group.

3. The condensed cyclic compound of claim 1 , wherein R 1 to R 8 , R 1 to R 15 , R 17 , R 22 to R 25 , R 37 and R 38 are each independently selected from hydrogen, deuterium, a cyano group, and groups represented by Formulae 4-1 to 4-29:

wherein * in Formulae 4-1 to 4-29 indicates a binding site to an adjacent atom.

4. The condensed cyclic compound of claim 1 , wherein
R 17 in Formula 2A-4 is selected from a cyano group and groups represented by Formulae 4-1 to 4-29:

wherein, in Formula 4-1 to 4-29, * indicates a binding site to an adjacent atom.

5. The condensed cyclic compound of claim 1 , wherein the number of cyano groups in Formula 2A-4 is 1, 2, 3, or 4.

6. The condensed cyclic compound of claim 1 , wherein each of the condensed cyclic compounds has a difference between a triplet (T 1 ) energy level and a singlet (S 1 ) energy level in a range from about 0.1 electron Volts to about 0.6 electron Volts.

7. The condensed cyclic compound of claim 1 , wherein each of the condensed cyclic compounds has a triplet (T 1 ) energy level in a range from about 2.9 electron Volts to about 3.1 electron Volts.

8. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 of claim 1 .

9. The organic light-emitting device of claim 8 , wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer comprises
a hole transport region disposed between the first electrode and the emission layer, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
an electron transport region disposed between the emission layer and the second electrode, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

10. The organic light-emitting device of claim 8 , wherein the emission layer comprises the at least one condensed cyclic compound represented by Formula 1.

11. The organic light-emitting device of claim 10 , wherein the emission layer further comprises a phosphorescent dopant comprising an organometallic compound represented by Formula 81:
M(L 81 ) n81 (L 82 ) n82   Formula 81

wherein, in Formula 81,
M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, and Rh,
L 81 is a ligand represented by Formula 81A,
n81 is an integer selected from 1 to 3, provided that when n81 is 2 or greater, two or more groups L 81 are identical to or different from each other,
L 82 is an organic ligand,
n82 is an integer selected from 0 to 4, provided that when n82 is 2 or greater, two or more groups L 82 are identical to or different from each other,

wherein, in Formula 81A,
Y 81 to Y 84 are each independently C or N,
Y 81 and Y 82 are linked to each other via a single bond or a double bond, and Y 83 and Y 84 are linked to each other via a single bond or a double bond,
CY 81 and CY 82 are each independently selected from a C 5 -C 30 carbocyclic group and a C 3 -C 30 h

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Hyunjung
• Chae Miyoung
• Kwon Eunsuk
• Kim Sangmo
• Jeon Soonok
• Chung Yeonsook
• Huh Dalho
• Park Youngseok
• Son Youngmok

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D409/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title