Light-emitting device and electronic apparatus including same

Patent metadata

Field	Value
Publication number	US-12520717-B2
Application number	US-202117305557-A
Country	US
Kind code	B2
Filing date	Jul 9, 2021
Priority date	Jul 13, 2020
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

A light-emitting device includes a first compound represented by Formula 1; and a second compound, a third compound, a fourth compound, or any combination thereof, each having a specific formula: emitting device may have excellent driving voltage, current density, high luminescence efficiency, and long lifespan, and may be used in the manufacture of a high quality electronic apparatus.

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, the interlayer comprising an emission layer, wherein the interlayer further comprises: i) a first compound represented by Formula 1; and ii) a second compound comprising at least one π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, a third compound comprising a group represented by Formula 3, or a fourth compound capable of emitting delayed fluorescent light, or any combination thereof, and the first compound, the second compound, the third compound, and the fourth compound are different from one another:

wherein, in Formula 1, M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
in Formula 1, X 1 to X 3 are C and X 4 is N,
in Formula 1, i) a bond between X 1 and M is a coordinate bond, and ii) one of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a coordinate bond, and the other two bonds are each a covalent bond,
in Formula 1, ring CY 1 is i) a X 1 -containing 5-membered ring, or ii) a X 1 -containing 5-membered ring condensed with at least one 6-membered ring,
wherein the X 1 -containing 5-membered ring in ring CY 1 in Formula 1 is a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, or a thiadiazole group, and
the 6-membered ring that is condensed with the X 1 -containing 5-membered ring in ring CY 1 in Formula 1 is a benzene group, a pyridine group, or a pyrimidine group,
in Formula 1, ring CY 2 is a benzene group, a pyridine group, a pyrimidine group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group,
in Formula 1, X 31 to X 36 and X 41 to X 44 are each independently C,
in Formula 1, X 51 is *—N(R 5 )—*′, *—B(R 5 )—*′, *—P(R 5 )—*′, *—C(R 5a )(R 5b )—*, *—Si(R 5a )(R 5b )—*′, *—Ge(R 5a )(R 5b )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 5 )=*′, *=C(R 5 )—*′, *—C(R 5a )═C(R 5b )—*′, *—C(═S)—*′, or *—C≡C—*′, and * and *′ each indicate a binding site to an adjacent atom,
in Formula 1, L 1 is a single bond, 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 ,
in Formula 1, b1 is an integer from 1 to 5,
in Formula 1, R 1 to R 5 , R 5a , and R 5b are each independently a group represented by Formula 1-1, 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 , provided that the C 1 -C 60 alkyl group is not substituted with a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, 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 , —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 ),

wherein, in Formula 1, c1 is an integer from 0 to 5, a1 and a4 are each independently an integer from 0 to 4, a2 is an integer from 0 to 10, and a3 is an integer from 0 to 6, provided that the sum of a1 to a4 is 1 or greater, and at least one of *-(L 1 ) b1 -(R 1 ) c1 (s) in the number of a1, at least one of R 2 (s) in the number of a2, at least one of R 3 (s) in the number of a3, or at least one of R 4 (s) in the number of a4, or any combination thereof are each independently the group represented by Formula 1-1,
in Formula 1-1, L 7 is a single bond, 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 ,
in Formula 1-1, b7 is an integer from 1 to 5,
in Formula 1-1, ring CY 7 is a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
in Formula 1-1, n7 is an integer from 1 to 5,
in Formula 1-1, ring CY 8 is a non-aromatic C 3 -C 60 carbocyclic group or a non-aromatic C 1 -C 60 heterocyclic group,
in Formula 1-1, R 7 and R 8 are each understood by referring to the description of R 1 ,
in Formula 1-1, a7 and a8 are each independently an integer from 0 to 20,
in Formula 3, ring CY 71 and ring CY 72 are each independently a π electron-rich C 3 -C 60 cyclic group or a pyridine group,
in Formula 3, X 71 is a single bond or a linking group comprising O, S, N, B, C, or Si, or any combination thereof,
in Formula 3, * indicates a binding site to an adjacent atom,
at least two groups represented by *-(L 1 ) b1 -(R 1 ) c1 in the number of a1 are optionally bound 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 ,
at least two of R 2 (s) in the number of a2 are optionally bound 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 ,
at least two of R 3 (s) in the number of a3 are optionally bound 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 ,
at least two of R 4 (s) in the number of a4 are optionally bound 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 ,
at least two of R 1 to R 5 , R 5a , and R 5b (s) are optionally bound 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, each independently 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 ), or —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 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

Assignees

• Samsung Display Co Ltd

Inventors

• Ko Soobyung
• Shin Sujin
• Ahn Eunsoo
• Lyu Jaejin
• Lee Jihyung
• HAN Junghoon

Classifications

• H10K85/658

  Organoboranes · CPC title

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• C07F1/00

  Compounds containing elements of Groups 1 or 11 of the Periodic Table · CPC title

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title