IP Library › Granted Patent US 12,022,726
Granted Patent B2
US 12,022,726 · App. 17/082,804 · Granted Jun 25, 2024

Organic light-emitting device and electronic apparatus including same

Inventors: Heejoo Ko (Yongin-si, KR); Eunhye Song (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/346H10K85/322H10K85/40H10K85/636H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/12H10K50/15H10K50/16H10K50/84
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Quick Facts
Patent No.
US 12,022,726
App. No.
17/082,804
Granted
Jun 25, 2024
Kind
B2
Abstract

Provided is an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the emission layer may include a host and a dopant, the host may include a first compound and a second compound different from the first compound, the dopant may include a third compound and a fourth compound different from the third compound, and the third compound may be a platinum-containing organometallic compound.

Claims (68)

1. An organic light-emitting device comprising:

a first electrode; a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein the emission layer comprises a host and a dopant, the host comprises a first compound and a second compound different from the first compound, the dopant comprises a third compound and a fourth compound different from the third compound, and the third compound is a platinum-containing organometallic compound, and wherein a y coordinate among CIE color-coordinates of light emitted from the emission layer is in a range of about 0.045 to about 0.06.

2. The organic light-emitting device of claim 1 , wherein a weight ratio of the third compound to the fourth compound in the emission layer is in a range of about 100:1 to about 1:100.

3. The organic light-emitting device of claim 1 , wherein the first compound is a hole-transporting host, and

the second compound is an electron-transporting host.

4. The organic light-emitting device of claim 1 , wherein the first compound comprises at least one moiety represented by any one selected from Formulae 3-1 to 3-3:

wherein, in Formulae 3-1 to 3-3,

X 31 is selected from O, S, N-(L 33 ) a33 -(R 33 ) b33 , C(R 33 )(R 34 ), and Si(R 33 )(R 34 ), CY 31 and CY 32 are each independently a π-electron rich cyclic group,

L 33 is selected from a single bond, a substituted or unsubstituted C 5 -C 30 carbocyclic group, and a substituted or unsubstituted C 1 -C 30 heterocyclic group,

a33 is an integer from 1 to 10, R 33 and R 34 are each independently selected from 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —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 ), b33 is an integer from 1 to 10, and

*, *′ and *″ each indicate a binding site to an adjacent atom.

5. The organic light-emitting device of claim 1 , wherein the first compound is selected from compounds represented by Formulae 3-11 to 3-14:

wherein, in Formula 3-11,

CY 31 and ring CY 32 are each independently a π-electron rich cyclic group having 3 to 30 carbon atoms, X 31 is selected from O, S, N-(L 33 ) a33 -(R 33 ) b33 , C(R 33 )(R 34 ), and Si(R 33 )(R 34 ), c31 and c32 are each independently an integer from 0 to 3,

wherein, in Formulae 3-11 to 3-14, L 31 to L 33 and L 41 to L 47 are each independently selected from a single bond, a substituted or unsubstituted C 5 -C 30 carbocyclic group, and a substituted or unsubstituted C 1 -C 30 heterocyclic group,

a31 to a33 and a41 to a47 are each independently an integer from 1 to 10,

R 31 to R 34 and R 41 to R 46 are each independently selected from 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —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 ), b31 to b33 and b41 to b46 are each independently an integer from 1 to 10, and at least one substituent of the substituted C 6 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: 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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 11 )(Q 12 );

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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 21 )(Q 22 ); and

—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 ), and —P(═O)(Q 31 )(Q 32 ), 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 selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 aryl group substituted with a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

6. The organic light-emitting device of claim 1 , wherein the second compound comprises an electron-transporting moiety comprising at least one selected from —F, a cyano group, a C 1 -C 60 alkyl group substituted with —F or a cyano group, a C 6 -C 60 aryl group substituted with —F or a cyano group, and a π-electron-depleted nitrogen-containing cyclic group.

7. The organic light-emitting device of claim 1 , wherein the second compound is a compound represented by Formula 4-1:

wherein, in Formula 4-1, X 51 is N or C[(L 54 ) a54 -(R 54 ) b54 ], X 52 is N or C[(L 55 ) a55 -(R 55 ) b55 ], and X 53 is N or C[(L 56 ) a56 -(R 56 ) b56 ], L 51 to L 56 are each independently selected from a single bond, a substituted or unsubstituted C 5 -C 30 carbocyclic group, and a substituted or unsubstituted C 1 -C 30 heterocyclic group, a51 to a56 are each independently an integer from 1 to 10, R 51 to R 56 are each independently selected from 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —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 ), b51 to b56 are each independently an integer from 1 to 10, and at least one substituent of the substituted C 6 -C 30 carbocyclic group, the substituted C 1 -C 30 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 11 )(Q 12 );

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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 21 )(Q 22 ); and

—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 ), and —P(═O)(Q 31 )(Q 32 ), 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 selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 aryl group substituted with a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

8. The organic light-emitting device of claim 1 , wherein the third compound and the fourth compound are each independently an organometallic compound represented by Formula 1:

wherein, in Formulae 1 and 1A to 1C, M is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal, wherein M in the third compound is platinum (Pt), L 1 is selected from a ligand represented by Formula 1A, a ligand represented by Formula 1B, and a ligand represented by Formula 1C, L 2 is selected from a monodentate ligand, a bidentate ligand, and a tridentate ligand, n1 is selected from 1, 2, and 3, n2 is selected from 0, 1, 2, 3, and 4,

CY 1 to CY 4 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group, Y 1 to Y 4 are each independently selected from a single bond, a double bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 30 heteroarylene group, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R 5 )(R 6 )—*′, *—C(R 5 )═C(R 6 )—*′, *—C(R 5 )═*′, *—Si(R 5 )(R 6 )—*′, *—B(R 5 )—*′, *—N(R 5 )—*′, and *—P(R 5 )—*′, a1 to a3 are each independently selected from 1, 2, and 3,

a4 is selected from 0, 1, 2, and 3, and when a4 is 0, CY 2 and CY 4 are not connected to each other, T 1 to T 4 are each independently selected from a chemical bond, *—O—*′, *—S—*′, *—B(R 7 )—*′, *—N(R 7 )—*′, *—P(R 7 )—*′, *—C(R 7 )(R 8 )—*′, *—Si(R 7 )(R 8 )—*′, *—Ge(R 7 )(R 8 )—*′, *—C(═O)—*′, and *—C(═S)—*′, *1, *2, *3, and *4 are each a binding site to M, R 1 to R 8 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 5 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 5 -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, —C(Q 1 )(Q 2 )(Q 3 ), —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 ), and —P(═S)(Q 1 )(Q 2 ), wherein adjacent groups from among R 1 to R 8 are optionally bound to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, adjacent groups from among R 1 to R 8 and Y 1 to Y 4 are optionally bound to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,

b1 to b4 are each independently an integer from 0 to 10, and at least one substituent of the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 5 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 5 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 5 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from:

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, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from 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 5 -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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 11 )(Q 12 );

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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 21 )(Q 22 ); and —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 ), and —P(═O)(Q 31 )(Q 32 ),

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 selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 aryl group substituted with a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and * and *′ each indicate a binding site to an adjacent atom.

9. The organic light-emitting device of claim 8 , wherein the third compound and the fourth compound are each independently selected from compounds represented by Formulae 1-1 and 1-2:

wherein, in Formulae 1-1 and 1-2, M, L 2 , n1, n2, CY 1 to CY 4 , Y 1 to Y 3 , a1 to a3, T1 to T 4 , R 1 to R 4 , and b1 to b4 are respectively understood by referring to the descriptions of M, L 2 , n1, n2, CY 1 to CY 4 , Y 1 to Y 3 , a1 to a3, T 1 to T 4 , R 1 to R 4 , and b1 to b4 in Formulae 1 and 1A to 1C.

10. The organic light-emitting device of claim 1 , wherein the third compound is a compound represented by Formula 2-1, and

the fourth compound is a compound represented by Formula 2-2:

wherein, in Formulae 2-1 and 2-2,

M 1 is Pt,

M 2 is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal, CY 12 to CY 14 and CY 22 to CY 24 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group, A 11 , A 12 , A 21 , and A 22 are each independently N or P, X 11 to X 13 and X 21 to X 23 are each independently N or C, Y 11 to Y 13 are each independently selected from a single bond, a double bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 30 heteroarylene group, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R 15 )(R 16 )—*′, *—C(R 15 )═C(R 16 )—*′, *—C(R 15 )═*′, *—Si(R 15 )(R 16 )—*′, *—B(R 15 )—*′, *—N(R 15 )—*′, and *—P(R 15 )—*′, Y 21 to Y 23 are each independently selected from a single bond, a double bond, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 1 -C 30 heteroarylene group, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R 25 )(R 26 ) —*′, *—C(R 25 )═C(R 26 )—*′, *—C(R 25 )═*′, *—Si(R 25 )(R 26 )—*′, *—B(R 25 )—*′, *—N(R 25 )—*′, and *—P(R 26 )—*′, a11 to a13 are each independently selected from 1, 2, and 3, a21 to a23 are each independently selected from 1, 2, and 3,

T 11 to T 14 are each independently selected from a chemical bond, *—O—*′, *—S—*′, *—B(R 17 )—*′,*—N(R 17 )*′, *—P(R 17 )—*′, *—C(R 17 )(R 18 )—*′, *—Si(R 17 )(R 18 )—*′, *—Ge(R 17 )(R 18 )—*′, *—C(═O)—*′, and *—C(═S)—*′, T 21 to T 24 are each independently selected from a chemical bond, *—O—*′, *—S—*′, *—B(R 27 )—*′, *—N(R 27 )—*′, *—P(R 27 )—*′, *—C(R 27 )(R 28 )—*′, *—Si(R 27 )(R 28 )—*′, *—Ge(R 27 )(R 28 )—*′, *—C(═O)—*′, and *—C(═S)—*′, R 11a to R 11c , R 12 to R 18 , R 21a to R 21c , and R 22 to R 28 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —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 ), and —P(═S)(Q 1 )(Q 2 ), wherein adjacent groups from among R 11a to R 11c and R 12 to R 18 are optionally bound to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, and adjacent groups from among R 21a to R 21c and R 22 to R 28 are optionally bound from a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, b12 to b14 and b22 to b24 are each independently an integer from 0 to 10, and at least one substituent of the substituted C 6 -C 30 arylene group, the substituted C 1 -C 30 heteroarylene group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C 5 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from: 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, and a C 1 -C 60 alkoxy group; C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 11 )(Q 12 ); 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic 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 ), and —P(═O)(Q 21 )(Q 22 ); and —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 ), and —P(═O)(Q 31 )(Q 32 ), 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 selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 aryl group substituted with a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and * and *′ each indicate a binding site to an adjacent atom.

11. The organic light-emitting device of claim 10 , wherein, in Formula 2-1, at least one selected from R 11a to R 11c and R 14 is an electron-donating group, and in Formula 2-2, i) at least one selected from R 22 and R 23 is a substituent other than hydrogen, ii) Y 23 is *—N(R 25 )—*′, and R 25 is a substituted C 6 -C 60 aryl group, or iii) at least one selected from R 22 and R 23 is a substituent other than hydrogen, Y 23 is *—N(R 25 )—*′, and R 25 is a substituted C 6 -C 60 aryl group.

12. The organic light-emitting device of claim 11 , wherein the electron-donating group is a substituent selected from an iso-propyl group, a tert-butyl group, and groups represented by Formulae 10-1 to 10-61:

wherein, in Formulae 10-1 to 10-61, “i-Pr” represents an iso-propyl group, “t-Bu” represents a t-butyl group, “Ph” represents a phenyl group, and

* indicates a binding site to an adjacent atom.

13. The organic light-emitting device of claim 10 , wherein the third compound is an organometallic compound represented by Formula 2-1A or Formula 2-1B, and the fourth compound is an organometallic compound represented by Formula 2-2A:

wherein in Formulae 2-1A, 2-1B, and 2-2A, Z 11 is C(R 12a ) or N, Z 12 is C(R 12b ) or N, Z 13 is C(R 12c ) or N, Z 14 is C(R 13a ) or N, Z 15 is C(R 13b ) or N, Z 16 is C(R 13c ) or N, Z 17 is C(R 14a ) or N, Z 18 is C(R 14b ) or N, Z 19 is C(R 14c ) or N, Z 20 is C(R 14d ) or N, Z 31 is C(R 15a ) or N, Z 32 is C(R 15b ) or N, Z 33 is C(R 15c ) or N, and Z 34 is C(R 15d ) or N, Z 21 is C(R 22a ) or N, Z 22 is C(R 22b ) or N, Z 23 is C(R 22c ) or N, Z 24 is C(R 23a ) or N, Z 25 is C(R 23b ) or N, Z 27 is C(R 24a ) or N, Z 28 is C(R 24b ) or N, Z 29 is C(R 24c ) or N, Z 30 is C(R 24d ) or N, Z 41 is C(R 25a ) or N, Z 42 is C(R 25b ) or N, Z 43 is C(R 25c ) or N, and Z 44 is C(R 25d ) or N, R 12a to R 12c are each understood by referring to the description of R 12 in Formula 2-1,

R 13a to R 13c are each understood by referring to the description of R 13 in Formula 2-1,

R 14a to R 14d are each understood by referring to the description of R 14 in Formula 2-1,

R 15a to R 15d are each understood by referring to the description of R 15 in Formula 2-1,

R 22a to R 22c are each understood by referring to the description of R 22 in Formula 2-2,

R 23a to R 23c are each understood by referring to the description of R 23 in Formula 2-2,

R 24a to R 24d are each understood by referring to the description of R 24 in Formula 2-2,

R 25a to R 25d are each understood by referring to the description of R 25 in Formula 2-2, and

M 1 , M 2 , CY 12 to CY 14 , CY 22 to CY 24 , A 11 , A 12 , A 21 , A 22 , X 11 to X 13 , X 21 to X 23 , Y 11 to Y 13 , Y 21 to Y 23 , a11 to a13, a21 to a23, T 11 to T 14 , T 21 to T 24 , R 11a to R 11c , and R 21a to R 21c are respectively understood by referring to the descriptions of M 1 , M 2 , CY 12 to CY 14 , CY 22 to CY 24 , A 11 , A 12 , A 21 , A 22 , X 11 to X 13 , X 21 to X 23 , Y 11 to Y 13 , Y 21 to Y 23 , a11 to a13, a21 to a23, T 11 to T 14 , T 21 to T 24 , R 11a to R 11c , and R 21a to R 21c in Formulae 2-1 and 2-2.

14. The organic light-emitting device of claim 1 , wherein the total content of the third compound and the fourth compound is in a range of about 1 percent by volume (vol %) to about 50 vol %, based on the total volume of the first compound and the second compound in the emission layer.

15. The organic light-emitting device of claim 1 , further comprising a capping layer on the second electrode,

wherein the capping layer has a refractive index of 1.6 or greater at a wavelength of 589 nanometers (nm).

16. The organic light-emitting device of claim 1 , wherein the emission layer comprises a first emission layer and a second emission layer,

the first emission layer is between the first electrode and the second emission layer, the first emission layer comprises the first compound, the second compound, and a first dopant, the second emission layer comprises the first compound, the second compound, and a second dopant, the first dopant is one selected from the third compound and the fourth compound, and the second dopant is different from the first dopant and is the other one selected from the third compound and the fourth compound.

17. The organic light-emitting device of claim 16 , wherein a difference between a maximum emission wavelength of light emitted from the first emission layer and a maximum emission wavelength of light emitted from the second emission layer is in a range of about 0 nm to about 35 nm.

18. The organic light-emitting device of claim 1 , wherein the emission layer comprises a first emission layer, a second emission layer, and a third emission layer, the first emission layer is between the first electrode and the second emission layer, the second emission layer is between the first electrode and the third emission layer, the first emission layer comprises the first compound, the second compound, and a first dopant, the second emission layer comprises the first compound, the second compound, and a second dopant, the third emission layer comprises the first compound, the second compound, and a third dopant,

the first dopant and the third dopant are each one selected from the third compound and the fourth compound, and the second dopant is different from the first dopant and the third dopant and is the other one selected from the third compound and the fourth compound.

19. An electronic apparatus comprising: a thin-film transistor comprising a source electrode, a drain electrode, and an active layer; and the organic light-emitting device of claim 1 , wherein the first electrode of the organic light-emitting device is electrically coupled to any one selected from the source electrode and the drain electrode of the thin-film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2020
From: KO, HEEJOO; SONG, EUNHYE
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 054199/0126 →
Priority Claims (1)
KR 10-2020-0054777 · May 7, 2020 · national
Continuity (1)
Related Publication 20210359226A1 · Nov 18, 2021