IP Library Granted Patent US 12,698,439
Granted Patent B2
US 12,698,439 · App. 18/110,331 · Granted Aug 4, 2026

Organic light-emitting device and electronic apparatus including the same

Inventors: Jongwoo Kim (Yongin-si, KR); Jangyeol Baek (Yongin-si, KR); Eunjae Jeong (Yongin-si, KR); Sanghyun Han (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C09K11/06H10K50/15H10K50/171H10K50/844H10K85/615H10K85/621H10K85/654H10K85/6572H10K85/6574C09K2211/1033C09K2211/1059H10K50/11H10K50/181H10K85/324H10K85/633
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Quick Facts
Patent No.
US 12,698,439
App. No.
18/110,331
Filed
Feb 15, 2023
Granted
Aug 4, 2026
Kind
B2
Art Unit
1786
USPC
428/690
Abstract

An organic light-emitting device includes a first electrode, a second electrode facing the first electrode, an organic layer between the first electrode and the second electrode and including an emission layer, and at least one of a first layer and a second layer, wherein the first layer is positioned in a path where light generated in the emission layer is transmitted to the outside through the first electrode and the second layer is positioned in a path where the light generated in the emission layer is transmitted to the outside through the second electrode. The first layer and the second layer each include a compound having a certain formula.

Claims (99)

1 . An organic light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an organic layer between the first electrode and the second electrode and comprising an emission layer;

at least one of a first layer or a second layer, wherein the first layer is positioned on a side of the first electrode opposite the organic layer and the second layer is positioned on a side of the second electrode opposite the organic layer, and

a substrate directly on the at least one of the first layer or the second layer,

wherein the first layer and the second layer are each about 500 Å to about 800 Å in thickness,

wherein the first layer and the second layer each consist of a condensed cyclic compound represented by Formula 1 and optionally an amine-based compound:

 and

wherein, in Formulae 1 and 2-1 to 2-4,

Ar 1 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyrene group, a chrysene group, a triphenylene group, an indene group, a benzofluorene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a pyrrole group, an imidazole group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a triazine group, an indeno pyrazine group, an indeno pyridine group, a phenanthroline group, and a phenanthridine group,

c1 is 0 or 1,

L 1 to L 5 and L 9 are each independently selected from *—N(R 11 )—*′, *—B(R 11 )—*′, *—P(R 11 )—*′, *—Si(R 11 )(R 12 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 11 )═*′, *—C(═S)—*′, a substituted or unsubstituted C 1 -C 60 alkylene group, a substituted or unsubstituted C 2 -C 60 alkenylene group, a substituted or unsubstituted C 2 -C 60 alkynylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, wherein L 1 and L 2 are each not *—S—*′,

a2 to a5 and a9 are each independently an integer from 0 to 10,

a1 is an integer from 0 to 2,

R 1 is a group represented by Formula 2-1 or a group represented by Formula 2-2,

R 2 to R 5 are each independently selected from a group represented by Formula 2-3, a group represented by Formula 2-4, 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 60 cycloalkoxy 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 ),

R 6 to R 9 , R 11 , and R 12 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 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 60 cycloalkoxy 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 4 )(Q 5 )(Q 6 ), —N(Q 4 )(Q 5 ), —B(Q 4 )(Q 5 ), —C(═O)(Q 4 ), —S(═O) 2 (Q 4 ), and —P(═O)(Q 4 )(Q 5 ),

b1 is an integer from 1 to 10, wherein, when b1 is two or more, two or more *-(L 1 ) a1 -R 1 (s) are identical to or different from each other,

b2 is an integer from 1 to 10, wherein, when b2 is two or more, two or more *-(L 2 ) a2 -R 2 (s) are identical to or different from each other,

b4 is an integer from 0 to 5, wherein, when b4 is two or more, two or more *-(L 4 ) a4 -R 4 (s) are identical to or different from each other,

b5 is an integer from 0 to 6, wherein, when b5 is two or more, two or more *-(L 5 ) a5 -R 5 (s) are identical to or different from each other,

when all of [R 5 -(L 5 ) a5 ] b5 in Formula 1 is hydrogen, Ar 1 is not a benzene group,

at least one substituent of the substituted C 1 -C 60 alkylene group, the substituted C 2 -C 60 alkenylene group, the substituted C 2 -C 60 alkynylene group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, and the substituted C 2 -C 60 alkynyl group is selected from the group consisting of:

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 alkoxy group, and a C 3 -C 60 cycloalkoxy group;

a C 1 -C 60 alkoxy group, and a C 3 -C 60 cycloalkoxy 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 60 cycloalkoxy 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 ),

at least one substituent of the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 10 heterocycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 1 -C 10 heterocycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 1 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 60 cycloalkoxy 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 the group consisting of:

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, and a C 3 -C 60 cycloalkoxy 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, and a C 3 -C 60 cycloalkoxy 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 60 cycloalkoxy 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 ),

Q 1 to Q 6 , 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 60 cycloalkoxy 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 terphenyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryl group substituted with a C 1 -C 60 alkyl group, a C 1 -C 60 heteroaryl group substituted with a C 6 -C 60 aryl group, and a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and

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

2 . The organic light-emitting device of claim 1 , wherein Ar 1 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a pyrene group, a chrysene group, a triphenylene group, an indene group, a benzofluorene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrrole group, an imidazole group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a triazine group, an indeno pyrazine group, an indeno pyridine group, a phenanthroline group, and a phenanthridine group.

3 . The organic light-emitting device of claim 1 , wherein:

L 1 to L 5 and L 9 are each independently selected from the group consisting of:

*—S—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, a C 1 -C 20 alkylene group, a C 2 -C 20 alkenylene group, a C 2 -C 20 alkynylene group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a carbazolylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, an oxazolopyridinylene group, a thiazolopyridinylene group, a benzonaphthyridinylene group, an azafluorenylene group, an azaspiro-bifluorenylene group, an azacarbazolylene group, an azadibenzofuranylene group, an azadibenzothiophenylene group, and an azadibenzosilolylene group; and

a C 1 -C 20 alkylene group, a C 2 -C 20 alkenylene group, a C 2 -C 20 alkynylene group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-benzofluorene-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a pyrrolylene group, a thiophenylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an indolylene group, an isoindolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a carbazolylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, an oxazolopyridinylene group, a thiazolopyridinylene group, a benzonaphthyridinylene group, an azafluorenylene group, an azaspiro-bifluorenylene group, an azacarbazolylene group, an azadibenzofuranylene group, an azadibenzothiophenylene group, and an azadibenzosilolylene 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 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy 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, a terphenyl group, and —Si(Q 31 )(Q 32 )(Q 33 ),

Q 31 to Q 33 are each independently selected from the group consisting of:

a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group; and

a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, each substituted with at least one selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, and a quinazolinyl group, and

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

4 . The organic light-emitting device of claim 1 , wherein:

L 1 to L 5 and L 9 are each independently selected from *—S—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—[C(Z 1 )(Z 2 )] n1 -*′, and groups represented by Formulae 3-1 to 3-75:

wherein, in Formulae 3-1 to 3-75,

Y 1 is O, S, C(Z 3 )(Z 4 ), N(Z 3 ), or Si(Z 3 )(Z 4 ),

Z 1 to Z 4 are each independently selected from hydrogen, deuterium, —F, —CF 3 , —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 20 alkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ), Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,

d3 is an integer from 1 to 3,

d4 is an integer from 1 to 4,

d5 is an integer from 1 to 5,

d6 is an integer from 1 to 6,

d8 is an integer from 1 to 8,

n1 is an integer from 1 to 20, and

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

5 . The organic light-emitting device of claim 1 , wherein:

Ar 1 is selected from groups represented by Formulae 4-1 to 4-27, 4-47 to 4-56, 4-58 and 4-59, and

L 1 to L 5 and L 9 are each independently selected from *—O—*′, *—C(═O)—*′, *—CH 2 —*′, *—(CH 2 ) 2 —*′, *—(CH 2 ) 3 —*′, *—(CH 2 ) 4 —*′, *—(CH 2 ) 5 —*′, and groups represented by Formulae 4-1 to 4-58 and 4-60:

wherein *, *′, and *″ in Formulae 4-1 to 4-60 each indicate a binding site to a neighboring atom.

6 . The organic light-emitting device of claim 1 , wherein:

the group represented by Formula 2-1 is a group represented by Formula 2-1A:

wherein, in Formula 2-1A, L 3 , L 4 , a3, a4, R 3 , R 4 , and b4 are the same as described in claim 1 , and * indicates a binding site to a neighboring atom.

7 . The organic light-emitting device of claim 1 , wherein:

R 2 to R 5 are each independently selected from the group consisting of:

a group represented by Formula 2-3, a group represented by Formula 2-4, 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 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 1 )(Q 2 )(Q 3 ); and

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl 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 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

8 . The organic light-emitting device of claim 1 , wherein:

R 6 to R 9 , R 11 , and R 12 are each independently selected from the group consisting of:

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 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 4 )(Q 5 )(Q 6 ); and

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl 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 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 20 alkoxy group, a C 3 -C 20 cycloalkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a furanyl group, a benzofuranyl group, a dibenzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ), and

Q 4 to Q 6 and Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

9 . The organic light-emitting device of claim 1 , wherein:

the condensed cyclic compound is represented by one of Formulae 1A to 1D, and 1I to 1P:

 and

wherein, in Formulae 1A to 1D, and 1I to 1P,

L 1 , L 2 , a1, a2, R 1 , R 2 , and b2 are the same as described in claim 1 , and

L 21 , a21, and R 21 are respectively the same as described in connection with L 1 , a1, and R 1 .

10 . The organic light-emitting device of claim 9 , wherein, in Formulae 1M to 1O,

R 1 and R 21 are each a group represented by Formula 2-1; or

R 1 and R 21 are each a group represented by Formula 2-2.

11 . The organic light-emitting device of claim 1 , wherein the condensed cyclic compound is one of Compounds 1 to 15 and 17 to 205:

12 . The organic light-emitting device of claim 1 , wherein the condensed cyclic compound is to absorb light having a wavelength of about 400 nm to about 410 nm.

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

the first electrode is a transmissive electrode or a semi-transmissive electrode, and

the organic light-emitting device comprises the first layer.

14 . The organic light-emitting device of claim 13 , wherein the first layer is an ultraviolet-absorbing light-efficiency-enhancement layer.

15 . The organic light-emitting device of claim 1 , wherein the second layer directly contacts the second electrode.

16 . The organic light-emitting device of claim 1 , wherein the second layer is an ultraviolet-absorbing light-efficiency-enhancement layer.

17 . The organic light-emitting device of claim 1 , wherein:

the first electrode and the second electrode are each independently a transmissive electrode or a semi-transmissive electrode, and

the organic light-emitting device comprises the first layer and the second layer.

18 . An electronic apparatus comprising:

the organic light-emitting device of claim 1 ; and

a thin film transistor,

wherein the first electrode of the organic light-emitting device electrically contacts one of a source electrode and a drain electrode of the thin film transistor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 21, 2023
From: KIM, JONGWOO; BAEK, JANGYEOL; JEONG, EUNJAE; HAN, SANGHYUN; KIM, YOUNGKOOK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 063044/0698 →
Priority Claims (1)
KR 10-2017-0101344 · Aug 9, 2017 · national
Continuity (2)
Continuation 15908542 · Feb 28, 2018
Related Publication 20230209862A1 · Jun 29, 2023
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