Light-emitting device including heterocyclic compound, electronic apparatus including the light-emitting device, and the heterocyclic compound

Patent metadata

Field	Value
Publication number	US-2025212685-A1
Application number	US-202418926799-A
Country	US
Kind code	A1
Filing date	Oct 25, 2024
Priority date	Dec 19, 2023
Publication date	Jun 26, 2025
Grant date	—

Abstract

A light-emitting device including a heterocyclic compound represented by Formula 1, an electronic apparatus including the light-emitting device, and a heterocyclic compound represented by Formula 1 are provided.

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 comprising an emission layer, wherein: the first electrode is an anode, the second electrode is a cathode, the interlayer further comprises 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, and the electron transport region comprises a heterocyclic compound represented by Formula 1:

wherein, in Formula 1,
X 1 is carbon, and X 1 is bonded to another carbon or nitrogen atom in one of four directions of X 1 ,
ring CY1 is a C 3 -C 20 cycloalkyl group,
X 21 is C(Y 21 ) or N, X 22 is C(Y 22 ) or N, X 23 is C(Y 23 ) or N, and the number of N(s) among X 21 to X 23 is one or more,
R 11 , R 12 , R 21 , R 22 , R 3 , and Y 21 to Y 23 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 that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group that is unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkylthio group that is unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group that is unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group that is unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group that is unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —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 ),
a3 is an integer from 1 to 20,
L 1 and L 2 are each independently a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
n1 and n2 are each independently an integer from 1 to 5,
R 11 and L 1 are optionally bonded together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 12 and L 1 are optionally bonded together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
R 11 and R 12 are optionally bonded together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
two or more neighboring groups selected from among R 21 , R 22 , and Y 21 to Y 23 are optionally bonded together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,
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 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, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, or a C 2 -C 60 heteroarylalkyl group, each 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, a C 7 -C 60 arylalkyl group, a C 2 -C 60 heteroarylalkyl 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 ), and
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; or 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 1 -C 60 alkylthio group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 7 -C 60 arylalkyl group, or a C 2 -C 60 heteroarylalkyl group, each 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 hole transport region comprises 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 comprises a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

3 . The light-emitting device of claim 1 , wherein the electron transport region comprises an electron transport layer, and
the electron transport layer comprises the heterocyclic compound.

4 . The light-emitting device of claim 1 , wherein the emission layer comprises a first compound that is a transition metal-containing compound, a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 heterocyclic group, a third compound comprising a group represented by Formula 3, a fourth compound capable of emitting delayed fluorescence, or any combination thereof, and
the first compound, the second compound, the third compound, and the fourth compound are different from each other:

in Formula 3,
ring CY71 and ring CY72 being each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
X 71 being a single bond or a linking group comprising O, S, N, B, C, Si, or any combination thereof, and
* indicating a binding site to any atom included in a remaining part other than the group presented by Formula 3 in the third compound.

5 . The light-emitting device of claim 1 , wherein the emission layer is to emit blue light.

6 . An electronic apparatus comprising the light-emitting device of claim 1 .

7 . The electronic apparatus of claim 6 , further comprising a thin-film transistor,
wherein the thin-film transistor comprises a source electrode and a drain electrode, and

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Dongjun
• Pak Hankyu
• Park Hyunbin
• Yun Jinyoung
• Han Sanghyun

Classifications

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K50/16

  Electron transporting layers · CPC title

• H10K85/6572

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

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title