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

Patent metadata

Field	Value
Publication number	US-2024251663-A1
Application number	US-202318236882-A
Country	US
Kind code	A1
Filing date	Aug 22, 2023
Priority date	Dec 15, 2022
Publication date	Jul 25, 2024
Grant date	—

Abstract

A light-emitting device that includes an amine-containing compound. An electronic apparatus and an electronic equipment that includes the light-emitting device. Utilization of the amine-containing compound in the light-emitting device may enhance or improve the operating characteristics of the device, such as driving voltage, luminance, efficiency, and/or lifespan.

First claim

What is claimed is:

1 . A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; an interlayer located between the first electrode and the second electrode, the interlayer comprising an emission layer; and an amine-containing compound represented by Formula 1 or 2:

and
wherein, in Formulae 1 and 2,
L 1 , L 2 , and L 3 are each independently 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 ,
Ar 1 and Ar 2 are each independently a C 6 -C 60 aryl group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heteroaryl group unsubstituted or substituted with at least one R 10a ,
R 1 is 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 , —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 ),
R 2 and R 3 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 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 , —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 ),
a1, a2, a3, b2, and b3 are each independently an integer from 0 to 6,
when b3 is 1 or more and R 3 is not hydrogen, R 1 and R 3 are not linked to each other,
each R 10a independently 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 being 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 a 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 being 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 a 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
wherein Q 1 , Q 2 , Q 3 , Q 11 , Q 12 , Q 13 , Q 21 , Q 22 , Q 23 , Q 31 , Q 32 , and 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 3 -C 60 carbocyclic group, or a C 1 -C 60 heterocyclic group, each being 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 a combination thereof.

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

3 . The light-emitting device of claim 1 , wherein the interlayer comprises the amine-containing compound.

4 . The light-emitting device of claim 2 , wherein the hole transport region comprises the amine-containing compound.

5 . The light-emitting device of claim 2 , wherein
the hole transport layer comprises the amine-containing compound, and the hole transport layer is in direct contact with the emission layer.

6 . The light-emitting device of claim 2 ,
wherein the light-emitting device further comprises a capping layer external to the first electrode, and wherein the capping layer comprises the amine-containing compound.

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

8 . The electronic apparatus of claim 7 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or a combination thereof.

9 . An electronic equipment comprising the light-emitting device of claim 1 .

10 . The electronic equipment of claim 9 , wherein the electronic equipment is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor or outdoor light and/or light for signal, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet personal computer, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality or augmented reality display, a vehicle, a video wall with multiple displays tiled together, a theater or stadium screen, a phototherapy device, and/or a signboard.

11 . An amine-containing compound represented by Formula 1 or 2:

wherein, in Formulae 1 and 2,
L 1 , L 2 , and L 3 are each independently 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 ,
Ar 1 and Ar 2 are each independently a C 6 -C 60 aryl group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heteroaryl group unsubstituted or substituted with at least one R 10a ,
R 1 is 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 leas

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jeongmin
• Kim Minji
• Pak Hankyu
• Park Hyunbin
• Yoo Byeongwook
• Jo Sohee

Classifications

• C07C2603/74

  Adamantanes · CPC title

• C07C2603/18

  Fluorenes; Hydrogenated fluorenes · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• H10K85/615

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

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title