IP Library › Granted Patent US 12,295,253
Granted Patent B2
US 12,295,253 · App. 17/351,073 · Granted May 6, 2025

Light-emitting device and electronic apparatus including same

Inventors: Namsu Kang (Yongin-si, KR); Minho Park (Yongin-si, KR); Dongkyu Lee (Yongin-si, KR); Jongwon Lee (Yongin-si, KR); Hyunshik Lee (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/626H10K85/624H10K85/654H10K85/6572H10K50/11H10K50/15H10K50/16H10K50/17H10K50/18H10K50/19H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 12,295,253
App. No.
17/351,073
Granted
May 6, 2025
Kind
B2
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.

Claims (67)

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 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 ), and

wherein 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.

8. The light-emitting device of claim 1 , wherein the first emission unit further comprises an electron blocking layer between the hole injection layer or the hole transport layer and the first emission layer.

9. The light-emitting device of claim 8 , wherein the electron blocking layer comprises a material having a higher triplet energy level than a triplet energy level of a compound comprised in the first emission layer.

10. The light-emitting device of claim 1 , wherein m−1 hole transport region(s), excluding the first hole transport region in the first emission unit, do not comprise a hole transfer layer.

11. The light-emitting device of claim 1 , wherein m−1 hole transport region(s), excluding the first hole transport region in the first emission unit, each independently comprise a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the m electron transport regions each independently comprise a hole blocking layer, an electron transport layer, an electron injection layer, a buffer layer, or any combination thereof.

12. The light-emitting device of claim 1 , wherein

the m emission units are to emit blue light having a maximum emission wavelength of about 440 nanometers (nm) to about 510 nm.

13. The light-emitting device of claim 1 , wherein

m emission layers comprised in the m emission units each independently comprise a phosphorescent dopant, a fluorescent dopant, a delayed fluorescence material, or any combination thereof.

14. The light-emitting device of claim 1 , wherein

a ratio of a delayed fluorescence component to a sum of a fluorescence component and a delayed fluorescence component from measurement of transient electroluminescence (EL) of the light-emitting device is 30 percent (%) or higher.

15. The light-emitting device of claim 1 , wherein the first electrode has a work function of about −5.2 eV to about −4.8 eV.

16. The light-emitting device of claim 1 , further comprising a first capping layer outside the first electrode and a second capping layer outside the second electrode, wherein at least one of the first capping layer or the second capping layer comprises a material having a refractive index of 1.6 or higher at a wavelength of 589 nm.

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

18. The electronic apparatus of claim 17 , wherein a color-coordinate measured at a front viewing angle of the electronic apparatus is about 0.09 to about 0.15.

19. The electronic apparatus of claim 17 , further comprising: an encapsulation unit on the light-emitting device; and

a functional layer on the encapsulation unit, wherein the functional layer comprises a touchscreen layer, a polarization layer, a color filter, a color-conversion layer, or any combination thereof.

20. The electronic apparatus of claim 17 , comprising quantum dots or an optical member comprising the quantum dots, located on at least one traveling direction of light emitted from the light-emitting device.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2021
From: KANG, NAMSU; PARK, MINHO; LEE, DONGKYU; LEE, JONGWON; LEE, HYUNSHIK
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 056580/0488 →
Priority Claims (1)
KR 10-2020-0076759 · Jun 23, 2020 · national
Continuity (1)
Related Publication 20210408387A1 · Dec 30, 2021
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