Light-emitting device including fused-cyclic compound and electronic apparatus including the same

Patent metadata

Field	Value
Publication number	US-12428600-B2
Application number	US-202217673713-A
Country	US
Kind code	B2
Filing date	Feb 16, 2022
Priority date	Feb 17, 2021
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

A light-emitting device includes: a first electrode; a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emission layer, and at least one fused cyclic compound of Formula 1:

wherein, in Formula 1, the variables are defined herein.

First claim

What is claimed is:

1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode, and
an interlayer between the first electrode and the second electrode and including an emission layer, and
at least one fused cyclic compound of Formula 1:

wherein, in Formulae 1, 2A, and 2B,
X 1 to X 4 are each, independently from one another, N, O, S, or Se, with the proviso that at least one of X 1 to X 4 is N,
when X 1 to X 4 is O, S, or Se, Ar 51 , Ar 52 , Ar 53 and Ar 54 do not exist, when Ar 51 is present, X 1 is N, when Ar 52 is present, X 2 is N, when Ar 53 is present, X 3 is N, and when Ar 54 is present, X 4 is N,
ring A 1 to ring A 4 are each, independently from one another, a C 5 -C 20 carbocyclic group or a C 1 -C 20 heterocyclic group,
Ar 1 to Ar 4 and Ar 51 to Ar 54 are each, independently from one another, a group of Formula 2A, a group of Formula 2B, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , provided that at least two of Ar 1 to Ar 4 and Ar 51 to Ar 54 are each independently a group of Formula 2A or Formula 2B,
R 1 to R 6 , R 21 , and R 22 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
b1 to b4 are each, independently from one another, an integer from 1 to 10,
b21 is an integer from 1 to 4, and
b22 is an integer from 1 to 3,
* indicates a binding site to a neighboring atom,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group each independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof,
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group each independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof, or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ),
wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 3 -C 60 carbocyclic group, or a C 1 -C 60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

2. The light-emitting device of claim 1 , wherein the emission layer comprises the at least one fused cyclic compound.

3. The light-emitting device of claim 1 , wherein
the emission layer, comprises a host and a dopant,
an amount of the host in the emission layer is greater than an amount of the dopant in the emission layer, and
the dopant includes the at least one fused cyclic compound.

4. The light-emitting device of claim 3 , wherein the at least one fused cyclic compound comprises a thermally activated delayed fluorescence emitter.

5. The light-emitting device of claim 2 , wherein the emission layer is configured to emit blue light having a maximum emission wavelength of about 410 nm to about 480 nm.

6. The light-emitting device of claim 1 , wherein
the first electrode comprises an anode,
the second electrode comprises a cathode,
the interlayer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
the hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron-blocking layer, or any combination thereof, and
the electron transport region includes a buffer layer, an electron control layer, a hole-blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

7. The light-emitting device of claim 1 , wherein
the first electrode comprises an anode,
the second electrode comprises a cathode,
the interlayer further includes a hole transport region between the first electrode and the emission layer,
the hole transport region includes a compound of Formula 201, a compound of Formula 202, or any combination thereof,
the emission layer includes the at least one fused cyclic compound of Formula 1:

wherein, in Formulae 201 and 202,
L 201 to L 204 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
L 20 S is *—O—*′, *—S—*′, *—N(Q 201 )-*′, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 2 -C 20 alkenylene group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
xa1 to xa4 are each, independently from one another, an integer from 0 to 5,
xa5 is an integer from 1 to 10,
R 201 to R 204 and Q 201 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,
R 201 and R 202 are optionally linked to each other via a single bond, a C 1 -C 5 alkylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 5 alkenylene group unsubstituted or substituted with at le

Assignees

• Samsung Display Co Ltd

Inventors

• Oh Chanseok
• Kim Seran
• Kim Taeil
• Pak Sunyoung
• Park Junha
• Baek Jangyeol
• Sunwoo Kyoung
• Sim Munki
• Jung Minjung

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title