Light-emitting device and electronic apparatus including same

Patent metadata

Field	Value
Publication number	US-12295253-B2
Application number	US-202117351073-A
Country	US
Kind code	B2
Filing date	Jun 17, 2021
Priority date	Jun 23, 2020
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

A light-emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode; and m−1 charge generation layer(s), each located between two adjacent emission units, and including m−1 n-type charge generation layer(s) and m−1 p-type charge generation layer(s). The m emission units each include a hole transport region, an emission layer, and an electron transport region. A first hole transport region in a first emission unit closest to the first electrode may include a hole transfer layer and a hole injection layer and/or a hole transport layer. The hole transfer layer may be a single layer consisting of an electron-transporting compound including a phosphine oxide group (P═O), a phosphine sulfide group (P═S), a π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, or any combination thereof. A highest occupied molecular orbital (HOMO) energy level of the hole transfer layer may be about −6.0 eV to about −5.3 eV.

First claim

What is claimed is:

1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
m emission units located between the first electrode and the second electrode; and
m−1 charge generation layer(s), each located between two adjacent emission units among the m emission units, and comprising m−1 n-type charge generation layer(s) and m−1 p-type charge generation layer(s),
wherein m is an integer of 2 or greater,
the m emission units each comprise a hole transport region, an emission layer, and an electron transport region, which are sequentially arranged,
a first hole transport region in a first emission unit closest among the m emission units to the first electrode comprises a hole transfer layer and at least one of a hole injection layer or a hole transport layer, which are sequentially arranged between the first electrode and a first emission layer in the first emission unit,
the hole transfer layer is a single layer consisting of an electron-transporting compound,
the electron-transporting compound comprises a phosphine oxide group (P═O), a phosphine sulfide group (P═S), a π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, or any combination thereof, and
a highest occupied molecular orbital (HOMO) energy level of the hole transfer layer is about −6.0 electron volts (eV) to about −5.3 eV.

2. The light-emitting device of claim 1 , wherein m is an integer of 3 or greater.

3. The light-emitting device of claim 1 , wherein the electron-transporting compound is represented by Formula 1 or Formula 2:
[Ar 1 ] a1 -[(L 1 ) b1 -R 1 ] c1   Formula 1

[Ar 2 ] a2 -[(L 2 ) b2 -R 2 ] c2 , and  Formula 2

wherein, in Formulae 1 and 2,
Ar 1 , Ar 2 , L 1 , and L 2 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 ,
a1 and a2 are each independently 1, 2, or 3,
b1 and b2 are each independently 0, 1, 2, 3, 4, or 5,
R 1 and R 2 are each independently 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 , —Si(Q 1 )(Q 2 )(Q 3 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ),
c1 and c2 are each independently 1, 2, 3, 4, or 5,
at least one of Ar 1 , L 1 , or R 1 is independently a π electron-deficient nitrogen-containing C 1 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , and
at least one R 2 group is —P(═O)(Q 1 )(Q 2 ) or —P(═S)(Q 1 )(Q 2 ),
wherein R 10a is deuterium (-D), —F, —C 1 , —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, —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 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 )
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 may each independently be 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 60 heterocyclic 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.

4. The light-emitting device of claim 3 , wherein at least one of Ar 1 , L 1 , or R 1 is independently selected from:
a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group; and
a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, each substituted with at least one R 10a .

5. The light-emitting device of claim 3 , wherein at least one of Ar 2 , L 2 , or R 2 is independently a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a .

6. The light-emitting device of claim 1 , wherein a difference between a HOMO energy level of the hole transfer layer and a HOMO energy level of the hole injection layer or hole transport layer adjacent to the hole transfer layer, is 0.15 eV or greater.

7. The light-emitting device of claim 1 , wherein the first emission layer comprises a compound represented by Formula 3:
[Ar 3 ] a3 -[(L 3 ) b3 -R 3 ] c3 , and  Formula 3

wherein, in Formula 3,
Ar 3 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 ,
a3 is 1, 2, or 3,
b3 is an integer from 0 to 5,
R 3 is 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 , 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 Q 1 to Q 3 are each independently hydrogen; deuterium; —F; —C 1 ; —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 60 heterocyclic 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,
c3 is an integer from 1 to 5, and
at least one of Ar 3 , L 3 , or R 3 is independently a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a ,
wherein 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 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 1 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60

Assignees

• Samsung Display Co Ltd

Inventors

• Kang Namsu
• Park Minho
• Lee Dongkyu
• Lee Jongwon
• Lee Hyunshik

Classifications

• H10K50/181

  Electron blocking layers · 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

• H10K2101/10

  Triplet emission · CPC title

• H10K50/19

  Tandem OLEDs · CPC title