Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11404646-B2
Application number	US-201916452833-A
Country	US
Kind code	B2
Filing date	Jun 26, 2019
Priority date	Jun 26, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode, wherein the emission layer includes a predetermined host and a thermally activated delayed fluorescence emitter.

First claim

What is claimed is:

1. An organic light-emitting device including:
a first electrode;
a second electrode facing the first electrode; and
an emission layer disposed between the first electrode and the second electrode,
wherein the emission layer comprises a host and a thermally activated delayed fluorescence emitter, and
the host comprises at least one compound selected from a compound represented by Formula 1 and a compound represented by Formula 2, and CZ in Formulae 1 and 2 is a group represented by Formula CZ1 or CZ2:

wherein, in Formulae 1, 2, CZ1, and CZ2,
rings A 1 , A 2 , A 5 , and A 6 are each independently a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzosilole group, a dibenzofuran group, or a dibenzothiophene group, wherein ring A 6 in Formula 2 is a dibenzofuran group or a dibenzothiophene group,
X 22 is O or S,
m is 0, 1, or 2,
n is 0 or 1,
Z 1 to Z 7 are each independently:
hydrogen, deuterium, or a cyano group (CN); or
a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one selected from deuterium, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, and a biphenyl group,
b1 to b6 are each independently 0, 1, 2, or 3,
*indicates a binding site to a neighboring atom, and
each of the compound represented by Formula 1 and the compound represented by Formula 2 includes at least one cyano group, and
wherein
a difference between a triplet energy level (electron volts) of the thermally activated delayed fluorescence emitter and a singlet energy level (electron volts) of the thermally activated delayed fluorescence emitter is in a range of about 0 electron volts to about 0.5 electron volts, and
the triplet energy level and the singlet energy level are evaluated by using a DFT method structurally optimized at a level of B3LYP/6-31G(d,p).

2. The organic light-emitting device of claim 1 , wherein
Z 1 to Z 7 are each independently:
hydrogen, deuterium, or a cyano group; or
a C 3 -C 10 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one selected from deuterium, a cyano group, a C 3 -C 10 alkyl group, a phenyl group, and a biphenyl group.

3. The organic light-emitting device of claim 1 , wherein
a number of the cyano groups included in the compound represented by Formula 1 and a number of the cyano groups included in the compound represented by Formula 2 are each independently 1, 2, 3, or 4.

4. The organic light-emitting device of claim 1 , wherein,
in Formulae 1 and 2,
at least one selected from groups Z 1 in the number of b1 and groups Z 2 in the number of b2 is a cyano group,
at least one selected from groups Z 3 in the number of b3 and groups Z 4 in the number of b4 is a cyano group,
at least one selected from groups Z 5 in the number of b5 and groups Z 6 in the number of b6 is a cyano group,
at least one selected from groups Z 1 in the number of b1 and groups Z 2 in the number of b2 is a cyano group, and at least one selected from groups Z 3 in the number of b3 and groups Z 4 in the number of b4 is a cyano group,
at least one selected from groups Z 1 in the number of b1 and groups Z 2 in the number of b2 is a cyano group, and at least one selected from groups Z 5 in the number of b5 and groups Z 6 in the number of b6 is a cyano group,
at least one selected from groups Z 3 in the number of b3 and groups Z 4 in the number of b4 is a cyano group, and at least one selected from groups Z 5 in the number of b5 and groups Z 6 in the number of b6 is a cyano group, or
at least one selected from groups Z 1 in the number of b1 and groups Z 2 in the number of b2 is a cyano group, at least one selected from groups Z 3 in the number of b3 and groups Z 4 in the number of b4 is a cyano group, and at least one selected from groups Z 5 in the number of b5 and groups Z 6 in the number of b6 is a cyano group.

5. The organic light-emitting device of claim 1 , wherein
CZ in Formulae 1 and 2 is a group represented by Formula CZ2,
Z 7 in Formula CZ2 is a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each substituted with at least one cyano group.

6. The organic light-emitting device of claim 1 , wherein a group represented by

in Formulae 1 and 2 is one selected from Formulae PO1 to PO25, PM1 to PM25, PP1 to PP18, MO1 to MO37, MM1 to MM37, MP1 to MP25, OO1 to OO37, OM1 to OM37, OP1 to OP25, O1 to O16, M1 to M16, and P1 to P9:

Assignees

• Samsung Electronics Co Ltd

Inventors

• Ihn Sooghang
• Sim Myungsun
• Jeong Daun
• Kim Jongsoo
• Kim Joonghyuk
• Lee Hasup
• Jeon Soonok
• Chung Yeonsook
• Jung Yongsik

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/6576 Primary

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title