Heterocyclic compound and light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12509476-B2
Application number	US-202117457396-A
Country	US
Kind code	B2
Filing date	Dec 2, 2021
Priority date	Dec 7, 2020
Publication date	Dec 30, 2025
Grant date	Dec 30, 2025

Abstract

The disclosure relates to a heterocyclic compound represented by Formula 1 and a light-emitting device including the same. The light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer including an emission layer between the first electrode and the second electrode, wherein the interlayer includes a heterocyclic compound represented by Formula 1.

First claim

What is claimed is:

1 . A light-emitting device comprising:
a first electrode; a second electrode facing the first electrode; an interlayer comprising an emission layer between the first electrode and the second electrode, wherein the interlayer comprises a heterocyclic compound represented by Formula 1:

wherein, in Formulae 1, 1-1, and 1-2,
A 1 zis a group represented by Formula 1-1,
B 1 is a group represented by Formula 1-2,
n is an integer selected from 1 to 6,
CY 1 and CY 2 are each a benzene group,
CY 3 to CY 6 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
R 1 and R 2 are each independently selected from 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 ), and —P(=O)(Q 1 )(Q 2 ),
R 3 , R 4 , R 5 and R 6 are each independently selected from a binding site to a B 1 group in Formula 1, 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 ), and —P(═O)Q 1 )(Q 2 ),
two or more neighboring groups of R 1 to R 6 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 least one R 10a to form 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 ,
b1 to b6 are each independently an integer selected from 1 to 10,
when b1 is an integer of 2 or more, two or more of R 1 (s) are identical to or different from each other, when b2 is an integer of 2 or more, two or more of R 2 (s) are identical to or different from each other, when b3 is an integer of 2 or more, two or more of R 3 (s) are identical to or different from each other, when b4 is an integer of 2 or more, two or more of R 4 (s) are identical to or different from each other, when b5 is an integer of 2 or more, two or more of R 5 (s) are identical to or different from each other, and when b6 is an integer of 2 or more, two or more of R 6 (s) are identical to or different from each other,
X 11 is C(R 11 ) or N,
X 12 is C(R 12 ) or N,
X 13 is C(R 13 ) or N,
X 14 is C(R 14 ) or N,
X 15 is C(R 15 ) or N,
X 16 is C(R 16 ) or N,
X 17 is C(R 17 ) or N,
X 18 is C(R 18 ) or N,
L 11 is 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 ,
a11 is an integer selected from 0 to 5,
when a11 is 0, *-(L 11 ) a11 -* is a single bond, and when a11 is an integer of 2 or more, two or more of L 11 ( s ) are identical to or different from each other,
indicates a binding site to a neighboring group,

R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are each independently selected from a binding site to an A 1 group in Formula 1, 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 ), and —P(═O)Q 1 )(Q 2 ),
two or more neighboring groups of R 11 to R 19 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 least one R 10a to form 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 , and
R 10a is:
deuterium (-D), —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, 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 -Coo carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, 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 ), and
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; or a C 3 -C 60 carbocyclic group or a C 1 -C

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Hyeongmin
• Ahn Heechoon
• Um Hyunah
• Lee Yeseul
• Lee Hyoyoung
• Im Yirang
• Cho Seowon

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

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

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title