IP Library › Granted Patent US 12,279,518
Granted Patent B2
US 12,279,518 · App. 17/281,665 · Granted Apr 15, 2025

Organic light-emitting device

Inventors: Sun Woo Kang (Yongin-si, KR); Sang Ho Jeon (Yongin-si, KR); Young Mi Cho (Yongin-si, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H10K85/346C09K11/06H10K85/342H10K85/626H10K85/654H10K85/6572C09K2211/1007C09K2211/1011C09K2211/1018C09K2211/104C09K2211/1044C09K2211/185H10K50/11H10K50/12H10K50/13H10K2101/10H10K2101/30H10K2101/40H10K2102/351
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Quick Facts
Patent No.
US 12,279,518
App. No.
17/281,665
Granted
Apr 15, 2025
Kind
B2
Abstract

Provided is an organic light-emitting device including: an anode; a cathode facing the anode; and an organic layer arranged between the anode and the cathode and including an emission layer and an auxiliary layer, wherein the emission layer is in direct contact with the auxiliary layer, the emission layer includes a dopant, the auxiliary layer includes a first compound and a second compound, and the dopant, the first compound, and the second compound satisfy a certain equation.

Claims (102)

1. An organic light-emitting device comprising:

an anode;

a cathode facing the anode; and

an organic layer arranged between the anode and the cathode and comprising an emission layer and an auxiliary layer,

wherein the emission layer is in direct contact with the auxiliary layer,

the emission layer comprises a dopant,

the auxiliary layer comprises a first compound and a second compound, and

the dopant, the first compound, and the second compound satisfy Equations 1 to 3:

wherein the dopant emits light, and each of the first compound and the second compound does not emit light:

T 1 ( D )> T 1 ( C 1)   Equation 1

S 1 ( D )< S 1 ( C 1)   Equation 2

S 1 ( C 1)< S 1 ( C 2)   Equation 3

wherein, in Equations 1 to 3,

T 1 (D) is a lowest excited triplet energy level of the dopant,

T 1 (C1) is a lowest excited triplet energy level of the first compound,

S 1 (D) is a lowest excited singlet energy level of the dopant,

S 1 (C1) is a lowest excited singlet energy level of the first compound, and

S 1 (C2) is a lowest excited singlet energy level of the second compound.

2. The organic light-emitting device of claim 1 , wherein the dopant emits blue phosphorescent light having a maximum emission wavelength of about 440 nm to about 480 nm.

3. The organic light-emitting device of claim 1 , wherein the first compound and the second compound further satisfy Equation 4:

T 1 ( C 1)> T 1 ( C 2)   Equation 4

wherein, in Equation 4,

T 1 (C1) is a lowest excited triplet energy level of the first compound, and

T 1 (C2) is a lowest excited triplet energy level of the second compound.

4. The organic light-emitting device of claim 1 , wherein the auxiliary layer is arranged between the anode and the emission layer.

5. The organic light-emitting device of claim 4 , wherein the emission layer further comprises a host, and

the dopant and the host further satisfy Equation 5:

HOMO ( D )> HOMO ( H )   Equation 5

wherein, in Equation 5,

HOMO(D) is a highest occupied molecular orbital energy level of the dopant, and

HOMO(H) is a highest occupied molecular orbital energy level of the host.

6. The organic light-emitting device of claim 1 , wherein the auxiliary layer is arranged between the cathode and the emission layer.

7. The organic light-emitting device of claim 6 , wherein the emission layer further comprises a host, and

the dopant and the host further satisfy Equation 6:

HOMO ( D )> HOMO ( H )   Equation 6

wherein, in Equation 6,

HOMO(D) is a highest occupied molecular orbital (HOMO) energy level of the dopant, and

HOMO(H) is a highest occupied molecular orbital energy level of the host.

8. The organic light-emitting device of claim 1 , wherein the dopant comprises a transition metal.

9. The organic light-emitting device of claim 1 , wherein the dopant is represented by Formula 1:

wherein, in Formulae 1 and 1A,

M 11 is a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, or a third-row transition metal of the Periodic Table of Elements;

L 11 is a ligand represented by Formula 1A, and n11 is 1, 2, or 3,

L 12 is an organic ligand, and n12 is an integer from 0 to 4,

X 11 to X 14 are each independently N or C, X 11 and X 12 are linked to each other via a single bond or a double bond, and X 13 and X 14 are linked to each other via a single bond or a double bond,

A 11 and A 12 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

Y 11 is a single bond, O, S, C(═O), N(Z 13 ), C(Z 13 )(Z 14 ), C(Z 13 )═C(Z 14 ), or C(Z 13 ), Y 11 and X 12 are linked to each other via a single bond or a double bond, and Y 11 and X 13 are linked to each other via a single bond or a double bond,

Z 11 and Z 12 are each independently a single bond, O, or S,

R 11 and R 12 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Z 15 )(Z 16 )(Z 17 ), —N(Z 15 )(Z 16 ), —B(Z 15 )(Z 16 ), —C(═O(Z 15 ), —S(═O) 2 (Z 15 ), —P(═O)(Z 15 )(Z 16 ), wherein two neighboring groups among R 11 and R 12 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C-C 30 heterocyclic group,

Z 13 and Z 14 are each independently hydrogen, deuterium, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

Z 15 to Z 17 are each independently a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group,

two, three, or four groups adjacent to each other among a plurality of R 11 and R 12 are optionally linked to each other to form a tetradentate, hexadentate, or octadentate ligand,

b11 and b12 are each independently an integer from 0 to 10, and

* and *' each indicate a binding site to M 11 in Formula 1.

10. The organic light-emitting device of claim 1 , wherein the dopant is compounds below:

11. The organic light-emitting device of claim 1 , wherein the first compound is represented by Formula 2:

wherein, in Formula 2,

X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), X 23 is N or C(R 23 ), X 24 is N or C(R 24 ), and X 25 is N or C(R 25 ), wherein at least one of X 21 to X 25 is N,

Y 21 is single bond, O, S, N(Z 21 ), or C(Z 21 )(Z 22 );

Y 22 is single bond, O, S, N(Z 23 ), or C(Z 23 )(Z 24 );

Y 23 is single bond, O, S, N(Z 25 ), or C(Z 25 )(Z 26 );

k21 to k23 are each independently 0, 1, or 2, wherein, when k21 is 0, Y 21 is not present, when k22 is 0, Y 22 is not present, and when k23 is 0, Y 23 is not present,

L 21 is an unsubstituted or substituted C 5 -C 60 carbocyclic group or an unsubstituted or substituted C 1 -C 60 heterocyclic group;

a21 is 0, 1, 2, or 3;

R 21 to R 28 and Z 21 to Z 26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ), wherein two neighboring groups among R 21 to R 28 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,

b26 is 1, 2, 3, or 4;

b27 and b28 are each independently 1, 2, 3; and

Q 1 to Q 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 10 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group.

12. The organic light-emitting device of claim 1 , wherein the first compound is one of the compounds below:

13. The organic light-emitting device of claim 1 , wherein the second compound is represented by Formula 3:

wherein, in Formula 3,

X 31 and X 32 are each independently substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

R 31 to R 38 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ), and

Q 1 to Q 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group.

14. The organic light-emitting device of claim 1 , wherein the second compound is compounds below:

15. The organic light-emitting device of claim 1 , wherein a thickness of the auxiliary layer is from 30 Å to 100 Å.

16. The organic light-emitting device of claim 1 , wherein the organic layer further comprises a hole transport region between the anode and the emission layer and/or an electron transport region between the emission layer and the cathode,

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

17. An organic light-emitting device comprising:

a substrate partitioned into a first subpixel area, a second subpixel area, and a third subpixel area;

a plurality of anodes arranged on each of the first subpixel area, the second subpixel area, and the third subpixel area of the substrate;

a cathode facing the plurality of anodes; and

an organic layer arranged between the plurality of anodes and the cathode and comprising a first emission layer, a second emission layer, and a third emission layer that are respectively arranged on the first subpixel area, the second subpixel area, and the third subpixel area of the substrate,

wherein the organic layer further comprises an auxiliary layer arranged on the first subpixel area,

the third emission layer comprises a dopant that emits light,

the auxiliary layer comprises a first compound and a second compound, and each of the first compound and the second compound does not emit light, and

the dopant, the first compound, and the second compound satisfy Equations 1 to 3:

T 1 ( D )> T 1 ( C 1)   Equation 1

S 1 ( D )< S 1 ( C 1)   Equation 2

S 1 ( C 1)< S 1 ( C 2)   Equation 3

S 1 (C1)<S 1 (C2)

wherein, in Equations 1 to 3,

T 1 (D) is a lowest excited triplet energy level of the dopant,

T 1 (C1) is a lowest triplet energy level of the first compound,

S 1 (D) is a lowest excited singlet energy level of the dopant,

S 1 (C1) is a lowest excited singlet energy level of the first compound, and

S 1 (C2) is a lowest excited singlet energy level of the second compound.

18. The organic light-emitting device of claim 17 , wherein the organic layer further comprises an auxiliary layer arranged on each of the second subpixel area and the third subpixel area.

19. The organic light-emitting device of claim 17 , wherein the first emission layer emits blue phosphorescence,

the second emission layer emits green phosphorescence, and

the third emission layer emits red phosphorescence.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2021
From: KANG, SUN WOO; JEON, SANG HO; CHO, YOUNG MI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 055848/0405 →
Priority Claims (2)
KR 10-2018-0134433 · Nov 5, 2018 · national
KR 10-2019-0071766 · Jun 17, 2019 · national
Continuity (1)
Related Publication 20220013737A1 · Jan 13, 2022
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