IP Library Granted Patent US 12,674,091
Granted Patent B2
US 12,674,091 · App. 16/919,858 · Granted Jul 7, 2026

Organic light-emitting device and device including same

Inventors: Hyosup Shin (Yongin-si, KR); Minje Kim (Yongin-si, KR); Eungdo Kim (Yongin-si, KR); Hyunyoung Kim (Yongin-si, KR); Hyojeong Kim (Yongin-si, KR); Seokgyu Yoon (Yongin-si, KR); Youngki Lee (Yongin-si, KR); Jungsub Lee (Yongin-si, KR); Jiyoung Lee (Yongin-si, KR); Hyejin Jung (Yongin-si, KR); Kunwook Cho (Yongin-si, KR); Hyeongu Cho (Yongin-si, KR); Minsoo Choi (Yongin-si, KR); Youngeun Choi (Yongin-si, KR); Jaejin Lyu (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C09K11/06H10K85/346H10K85/40H10K85/615H10K85/631H10K85/654H10K85/657H10K85/6572H10K85/658C09K2211/1044C09K2211/185H10K50/11H10K50/121H10K59/12H10K2101/10
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Quick Facts
Patent No.
US 12,674,091
App. No.
16/919,858
Filed
Jul 2, 2020
Granted
Jul 7, 2026
Kind
B2
Art Unit
1786
USPC
428/690
Abstract

An organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and the emission layer includes a first compound as a hole transport compound, a second compound as an electron transport compound, a third compound as a metal complex compound, and a fourth compound as a boron-based compound.

Claims (65)

1 . An organic light-emitting device comprising:

a first electrode,

a second electrode, and

an organic layer between the first electrode and the second electrode,

wherein the organic layer includes an emission layer, and

the emission layer includes a first compound as a hole transport compound, a second compound as an electron transport compound, a third compound as a metal complex compound, and a fourth compound as a boron-based compound, wherein the third compound and the fourth compound satisfy Equation 2:

A/B≥ 10%,  Equation 2

wherein, in Equation 2,

A=an overlapping area of the light absorption area of the fourth compound and a light-emission area of the third compound; and

B=the total light-emission area of the third compound,

wherein, the term “light absorption area of the fourth compound” refers to the area in the light absorption spectrum corresponding to light absorption from S 0 to S 1 , which are singlet energy states of the fourth compound, and the term “light-emission area of the third compound” refers to an area in the light emission spectrum corresponding to light emission from S 1 to S 0 , which are singlet energy states of the third compound, and

the light absorption area is measured using an absorption spectrum equipment and the light-emission area is measured using a luminescent spectrum equipment,

wherein the first compound is represented by Formula 1:

wherein, in Formula 1, R 1 , R 2 , and Ar 1 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), L 1 is selected from a substituted or unsubstituted C 4 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group, a1 and a2 are each independently an integer from 1 to 4, b1 is an integer from 0 to 3, at least one substituent of 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 4 -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 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 ), and 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 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 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,

wherein the second compound is represented by Formula 2:

wherein, in Formula 2,

Ar 11 to Ar 13 are each independently selected from hydrogen, deuterium, and Formulae 4a to 4e with the proviso that at least one of Ar 11 to Ar 13 comprises Formulae 4a or 4b,

wherein, in Formulae 4a to 4e, Z 10 to Z 19 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 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 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, az17 and az18 are each independently an integer from 1 to 7, az19 is an integer from 1 to 5, and * indicates a binding site to a neighboring atom,

L 11 to L 13 are each independently selected from a substituted or unsubstituted C 4 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,

b11 to b13 are each independently an integer from 0 to 3, at least one substituent of the substituted C 4 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from:

deuterium (-D), —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 ), and

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 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 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,

wherein when at least one of Ar 11 to Ar 13 comprises Formula 4b, then:

at least one of Ar 11 to Ar 13 comprises Formula 4a-4c; or

at least one of Ar 11 to Ar 13 comprises Formula 4d bonded to the central triazine moiety,

wherein the third compound is one of Compounds 5-8, 13-16, 25-28, and 33-36:

wherein the fourth compound is represented by Formula 4:

wherein, in Formula 4, Y 1 to Y 3 are each independently O, S, N(R 24 ), B(R 24 ), C(R 24 )(R 25 ), or Si(R 24 )(R 25 ), c is 0 or 1, A 11 to A 13 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group, R 21 to R 25 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), and R 21 to R 25 are optionally combined with each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, a21 to a23 are each independently an integer from 0 to 10, at least one substituent of 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 4 -C 60 carbocyclic group, and the substituted C 1 -C 60 heterocyclic group is selected from: deuterium (-D), —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 ), and 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 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 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.

2 . The organic light-emitting device of claim 1 , wherein a triplet energy value of the third compound (T 1 of third compound) and a triplet energy value of the fourth compound (T 1 of fourth compound) satisfy Equation 1:

T 1 of third compound− T 1 of fourth compound≤0.3eV  Equation 1

3 . The organic light-emitting device of claim 1 , wherein an average excitation time (tau) of the fourth compound is 20 μs or less.

4 . The organic light-emitting device of claim 1 , wherein R 1 , R 2 , and Ar 1 are each independently selected from hydrogen, deuterium, and groups represented by Formulae 2a to 2c:

wherein, in Formulae 2a to 2c, H 1 is NR 100 , O, or S, and Z 1 to Z 5 and R 100 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 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 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,

az1 is an integer from 1 to 5,

az2 and az3 are each independently an integer from 1 to 4,

az4 and az5 are each independently an integer from 1 to 3, and

* indicates a binding site to a neighboring atom.

5 . The organic light-emitting device of claim 1 , wherein L 1 is selected from Formulae 3a to 3c:

wherein, in Formulae 3a to 3c, Z 6 to Z 9 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 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 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,

az6 is an integer from 1 to 4,

az7 and az8 are each independently an integer from 1 to 7, and

* and *′ each indicate a binding site to a neighboring atom.

6 . The organic light-emitting device of claim 1 , wherein L 11 to L 13 are each independently selected from compounds represented by Formula 5a:

wherein, in Formula 5a, Z 20 is selected from hydrogen, deuterium, —F, —C 1 , —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 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,

az20 is an integer from 1 to 4, and

* and *′ each indicate a binding site to a neighboring atom.

7 . The organic light-emitting device of claim 1 , wherein Formula 4 is represented by one of Formulae 4-1 and 4-2:

wherein, in Formulae 4-1 and 4-2, Y 2 to Y 5 are each independently O, S, N(R 44 ), B(R 44 ), C(R 44 )(R 45 ), or Si(R 44 )(R 45 ), and

R 31a to R 31d , R 32a to R 32d , R 33a to R 33c , R 34a to R 34d , R 35a to R 35c , and R 44 and R 45 have the same definitions as R 21 in Formula 4.

8 . The organic light-emitting device of claim 7 , wherein R 31a to R 31d , R 32a to R 32d , R 33a to R 33c , R 34a to R 34d , R 35a to R 35c , and R 44 and R 45 are each independently selected from a C 1 -C 60 alkyl group and groups represented by Formulae 6a to 6c:

wherein, in Formulae 6a to 6c, Z 21 to Z 24 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 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 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,

az21 to az23 are each independently an integer from 1 to 5,

az24 is an integer from 1 to 8, and

* indicates a binding site to a neighboring atom.

9 . The organic light-emitting device of claim 1 , wherein the first compound is one of Compounds HT-01 to HT-17,

the second compound is one of Compounds ET01, ET03, ET04, ET06, ET07, ET09, ET010, ET012, and ET015, and

the fourth compound is one of Compounds D-01 to D-22:

10 . An electronic apparatus comprising:

a thin-film transistor and the organic light-emitting device of claim 1 , wherein the thin-film transistor includes a source electrode, a drain electrode, an activation layer, and a gate electrode, and

the first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.

11 . The organic light-emitting device of claim 1 , wherein the third compound and the fourth compound include at least one of the following combinations:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2020
From: SHIN, HYOSUP; KIM, MINJE; KIM, EUNGDO; KIM, HYUNYOUNG; KIM, HYOJEONG; YOON, SEOKGYU; LEE, YOUNGKI; LEE, JUNGSUB; LEE, JIYOUNG; JUNG, HYEJIN; CHO, KUNWOOK; CHO, HYEONGU; CHOI, MINSOO; CHOI, YOUNGEUN; LYU, JAEJIN
To: SAMSUNG DISPLAY CO., LTD.
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KR 10-2019-0123358 · Oct 4, 2019 · national
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Related Publication 20210104682A1 · Apr 8, 2021
References Cited (148)
US 9604928B2 · Shitagaki et al. · 2017 [cited by applicant]
US 9666817B2 · Kim et al. · 2017 [cited by applicant]
US 9741939B2 · Kim et al. · 2017 [cited by applicant]
US 9923155B2 · Li et al. · 2018 [cited by applicant]
US 9980358B2 · Kim · 2018 [cited by applicant]
US 9985233B2 · Hashimoto et al. · 2018 [cited by applicant]
US 10008676B2 · Han et al. · 2018 [cited by applicant]
US 10062850B2 · Jung et al. · 2018 [cited by applicant]
US 10090483B2 · Kim et al. · 2018 [cited by applicant]
US 10374166B2 · Hatakeyama et al. · 2019 [cited by applicant]
US 10418573B2 · Kim et al. · 2019 [cited by applicant]
US 10431766B2 · Ito et al. · 2019 [cited by applicant]
US 10886478B2 · Li et al. · 2021 [cited by applicant]
US 10916715B2 · Koe et al. · 2021 [cited by applicant]
US 11289660B2 · Lee et al. · 2022 [cited by applicant]
US 11316124B2 · Ito et al. · 2022 [cited by applicant]
US 11482680B2 · Kim et al. · 2022 [cited by applicant]
US 11696499B2 · Cho et al. · 2023 [cited by applicant]
US 20130264560A1 · Dobbs · 2013 [cited by examiner]
US 20130264561A1 · Dobbs · 2013 [cited by examiner]
US 20140077172A1 · So et al. · 2014 [cited by applicant]
US 20150001502A1 · Seo et al. · 2015 [cited by applicant]
US 20150105556A1 · Li · 2015 [cited by examiner]
US 20150207079A1 · Cho · 2015 [cited by examiner]
US 20150295197A1 · Adamovich et al. · 2015 [cited by applicant]
US 20160028028A1 · Li et al. · 2016 [cited by applicant]
US 20160087227A1 · Kim et al. · 2016 [cited by applicant]
US 20160164020A1 · Kim et al. · 2016 [cited by applicant]
US 20160233442A1 · Yen et al. · 2016 [cited by applicant]
US 20160301014A1 · Kawamura et al. · 2016 [cited by applicant]
US 20170179395A1 · Km et al. · 2017 [cited by applicant]
US 20170294613A1 · Cho et al. · 2017 [cited by applicant]
US 20170346029A1 · Kim et al. · 2017 [cited by applicant]
US 20180033987A1 · Kim et al. · 2018 [cited by applicant]
US 20180108857A1 · Adachi et al. · 2018 [cited by applicant]
US 20180151821A1 · Peng et al. · 2018 [cited by applicant]
US 20180312533A1 · Ahn et al. · 2018 [cited by applicant]
US 20180323394A1 · Haldi et al. · 2018 [cited by applicant]
US 20180337361A1 · Lee et al. · 2018 [cited by applicant]
US 20180375036A1 · Chen et al. · 2018 [cited by applicant]
US 20190013478A1 · Iijima et al. · 2019 [cited by applicant]
US 20190019964A1 · Jeon et al. · 2019 [cited by applicant]
US 20190019971A1 · Xie et al. · 2019 [cited by applicant]
US 20190036055A1 · Lin et al. · 2019 [cited by applicant]
US 20190058124A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190058137A1 · Ko et al. · 2019 [cited by applicant]
US 20190062312A1 · Zink · 2019 [cited by applicant]
US 20190067616A1 · Jeon et al. · 2019 [cited by applicant]
US 20190093009A1 · Yen et al. · 2019 [cited by applicant]
US 20190097155A1 · Kim et al. · 2019 [cited by applicant]
US 20190103564A1 · Ogawa et al. · 2019 [cited by applicant]
US 20190148640A1 · Lim et al. · 2019 [cited by applicant]
US 20190157351A1 · Kim et al. · 2019 [cited by applicant]
US 20190203114A1 · Ihn et al. · 2019 [cited by applicant]
US 20190207112A1 · Hatakeyama et al. · 2019 [cited by applicant]
US 20190296254A1 · Ko et al. · 2019 [cited by applicant]
US 20190393422A1 · Sakamoto · 2019 [cited by applicant]
US 20200083461A1 · Duan et al. · 2020 [cited by applicant]
US 20200136046A1 · Béalle et al. · 2020 [cited by applicant]
US 20200203651A1 · Duan et al. · 2020 [cited by applicant]
US 20200321539A1 · Zhao et al. · 2020 [cited by applicant]
US 20210098713A1 · Choi et al. · 2021 [cited by applicant]
US 20210098714A1 · Choi et al. · 2021 [cited by applicant]
US 20210098716A1 · Lee et al. · 2021 [cited by applicant]
US 20210098721A1 · Jung et al. · 2021 [cited by applicant]
US 20210104681A1 · Kim et al. · 2021 [cited by applicant]
US 20210292342A1 · Suzuki et al. · 2021 [cited by applicant]
US 20220024958A1 · Ko et al. · 2022 [cited by applicant]
US 20220131086A1 · Lee et al. · 2022 [cited by applicant]
US 20230127039A1 · Naijo et al. · 2023 [cited by applicant]
US 20230138754A1 · Lee et al. · 2023 [cited by applicant]
CN 106910831A · 2017 [cited by applicant]
CN 107275496A · 2017 [cited by applicant]
CN 107359257A · 2017 [cited by applicant]
CN 107408634A · 2017 [cited by applicant]
CN 108431984A · 2018 [cited by applicant]
CN 109075259A · 2018 [cited by applicant]
CN 109192874A · 2019 [cited by applicant]
CN 109786569A · 2019 [cited by applicant]
CN 110105281A · 2019 [cited by applicant]
CN 110299457A · 2019 [cited by applicant]
EP 3109253A1 · 2016 [cited by examiner]
EP 3435438A2 · 2019 [cited by applicant]
EP 3800683A1 · 2021 [cited by applicant]
JP 2004273190A · 2004 [cited by examiner]
JP 2011153276A · 2011 [cited by examiner]
JP 2016130231A · 2016 [cited by applicant]
JP 2019169710A · 2019 [cited by applicant]
KR 101219668B1 · 2013 [cited by applicant]
KR 101419810B1 · 2014 [cited by applicant]
KR 1020160012941A · 2016 [cited by applicant]
KR 1020160034528A · 2016 [cited by applicant]
KR 1020160039974A · 2016 [cited by applicant]
KR 101617877B1 · 2016 [cited by applicant]
KR 1020160067629A · 2016 [cited by applicant]
KR 1020160101519A · 2016 [cited by applicant]
KR 101646732B1 · 2016 [cited by applicant]
KR 1020160119683A · 2016 [cited by applicant]
KR 101680934B1 · 2016 [cited by applicant]
KR 1020170014797A · 2017 [cited by applicant]
KR 101706752B1 · 2017 [cited by applicant]
KR 1020170026075A · 2017 [cited by applicant]
KR 1020170078573A · 2017 [cited by applicant]
KR 1020170083960A · 2017 [cited by applicant]
KR 1020180013380A · 2018 [cited by applicant]
KR 1020180033094A · 2018 [cited by applicant]
KR 1020180043886A · 2018 [cited by applicant]
KR 1020180108604A · 2018 [cited by applicant]
KR 1020180120865A · 2018 [cited by applicant]
KR 20180134850A · 2018 [cited by applicant]
KR 1020190000812A · 2019 [cited by applicant]
KR 1020190008481A · 2019 [cited by applicant]
KR 1020190034126A · 2019 [cited by applicant]
WO WO2011081286A2 · 2011 [cited by examiner]
WO WO2016152605A1 · 2016 [cited by applicant]
WO 2019128105A1 · 2019 [cited by applicant]
JP-2004273190-A—translation (Year: 2004). [cited by examiner]
WO-2011081286-A2—translation (Year: 2011). [cited by examiner]
JP-2011153276-A—translation (Year: 2011). [cited by examiner]
Martin C. E. Huber, et al., “The measurement of oscillator strengths,” Reports on Progress in Physics, Institute of Physics Publishing, Bristol, GB, Vo. 49, No. 4, Apr. 1, 1986, pp. 397-490, XP020024846, DOI:10.1088/003… [cited by applicant]
Liang, Xiao, et al. “Peripheral amplification of multi-resonance induced thermally activated delayed fluorescence for highly efficient OLEDs.” Angewandte Chemie 130.35 (2018): 11486-11490. (Year: 2018). [cited by applicant]
US Office Action dated Feb. 3, 2023, issued in U.S. Appl. No. 16/997,715 (11 pages). [cited by applicant]
US Notice of Allowance dated Jun. 1, 2023, issued in U.S. Appl. No. 18/064,787 (8 pages). [cited by applicant]
US Notice of Allowance dated Jun. 28, 2023, issued in U.S. Appl. No. 16/997,715 (5 pages). [cited by applicant]
Chiu, et al., “High-Efficiency Blue Phosphorescence Organic Light-Emitting Diode with Ambipolar Carbozole-Triazole Host,” J. Phys. Chem. C (2015), vol. 119, pp. 16846-16852. [cited by applicant]
Choi, et al., “Simultaneous achievement of High Efficiency and Long Lifetime in Deep Blue Phosphorescent Organic Light-Emitting Diodes,” Advanced Optical Materials (2019), vol. 7, No. 23, pp. 1901374-1901374. [cited by applicant]
Finkenzeller, et al., “Emission of Ir(ppy) [cited by applicant]
Hatakeyama, et al., “Ultrapure Blue Thermally Activated Delayed Fluorescence Molecules: Efficient HOMO-LUMO Separation by the Multiple Resonance Effect,” Adv. Mater. (2016), vol. 28, pp. 2777-2781. [cited by applicant]
Hedley, et al., “Ultrafast Luminescence in Ir(ppy) [cited by applicant]
Huang, et al., “Investigation of Exciton Recombination Zone in Quantum Dot Light-Emitting Diodes Using a Fluorescent Probe”, ACS Appl. Mater. Interfaces (2017), vol. 9, pp. 27809-27816. [cited by applicant]
Joo, et al., “Development of Solution-Processable Blue/Hybrid-White OLEDs Based on Thermally Activated Delayed Fluorescence”, Journal of Industrial and Engineering Chemistry (2018), vol. 65, pp. 35-39. [cited by applicant]
Lee, et al., “Phosphor Sensitized Thermally Activated Delayed Fluorescence Organic Light-Emitting Diodes with Ideal Deep Blue Device Performances”, Journal of Materials Chemistry C (2019), vol. 7, pp. 8562-8568. [cited by applicant]
Li, et al. “Efficient and Stable White Organic Light-Emitting Diodes Employing a Single Emitter,” Adv. Mater. (2014), vol. 26, pp. 2931-2936. [cited by applicant]
Li, et al., “Efficient Solution-Processed Blue and White OLEDs Based on a High-Triplet Bipolar Host and a Blue TADF Emitter”, Organic Electronics (2018), vol. 58, pp. 276-282. [cited by applicant]
Office Action for U.S. Appl. No. 17/131,555 dated Oct. 18, 2023, 20 pages. [cited by applicant]
Park, et al., “High Efficiency of Over 25% and Long Device Lifetime of Over 500 h at 1000 nit in Blue Fluorescent Organic Light-Emitting Diodes” Adv. Mater. (2022), vol. 34, 7 pages. [cited by applicant]
Saghaei, et al., “Effect of PEDOT:PSS on the Performance of Solution-Processed Blue Phosphorescent Organic Light-emitting Diodes with an Exciplex Host,” Mater. Adv. (2022), vol. 3, pp. 1055-1063. [cited by applicant]
Zhao, et al., “Highly Efficient Red OLEDs Using DCJTB as the Dopant and Delayed Fluorescent Exciplex as the Host,” Scientific Reports (2015), vol. 5, 8 pages. [cited by applicant]
US Final Office Action dated Mar. 8, 2024, issued in U.S. Appl. No. 17/131,555 (19 pages). [cited by applicant]
Wong, Michael Y., and Eli Zysman-Colman. “Purely organic thermally activated delayed fluorescence materials for organic light-emitting diodes.” Advanced Materials 29.22 (2017): 1605444. (Year: 2017). [cited by applicant]
US Office Action dated Oct. 10, 2024, issued in U.S. Appl. No. 18/528,604 (8 pages). [cited by applicant]
US Office Action dated Oct. 10, 2024, issued in U.S. Appl. No. 17/131,555 (25 pages). [cited by applicant]
US Notice of Allowance dated Feb. 12, 2025, issued in U.S. Appl. No. 18/528,604 (6 pages). [cited by applicant]
Liu et al., “Novel bipolar host materials based on 1,3,5-triazine derivatives for highly efficient phosphorescent OLEDs with extremely low efficiency roll-off,” Phys. Chem. Chem: Phys, 2012, 14, pp. 14255-14261. [cited by applicant]
US Final Office Action dated Mar. 20, 2025, issued in U.S. Appl. No. 17/131,555 (20 pages). [cited by applicant]
Shin, Su Kyeong, et al., “High triplet energy exciplex host derived from a CN modified carbazole based n-type host for improved efficiency and lifetime in blue phosphorescent organic light-emitting diodes,” Journal of M… [cited by applicant]
US Office Action dated Sep. 24, 2025, issued in U.S. Appl. No. 17/131,555 (15 pages). [cited by applicant]
US Final Office Action dated Feb. 18, 2026, issued in U.S. Appl. No. 17/131,555 (13 pages). [cited by applicant]