US 12,089,430 B2
Organic light-emitting device and apparatus including the same
Yeongji Im, Yongin-si (KR); Jino Lim, Yongin-si (KR); Beomjin Kim, Yongin-si (KR); and Seunggak Yang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Feb. 24, 2021, as Appl. No. 17/249,231.
Claims priority of application No. 10-2020-0040483 (KR), filed on Apr. 2, 2020.
Prior Publication US 2021/0320273 A1, Oct. 14, 2021
Int. Cl. H10K 50/11 (2023.01); C09K 11/06 (2006.01); H10K 59/12 (2023.01); H10K 59/35 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01)
CPC H10K 50/11 (2023.02) [C09K 11/06 (2013.01); H10K 59/35 (2023.02); C09K 2211/1018 (2013.01); H10K 59/12 (2023.02); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/623 (2023.02); H10K 85/626 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/90 (2023.02)] 19 Claims
OG exemplary drawing
 
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 including an emission layer,
wherein the emission layer comprises a host and a dopant,
the host comprises a first compound and a second compound,
the first compound, the second compound, and the dopant are different from one another,
two compounds in the host included in the emission layer have different HOMO and LUMO energy levels, and form an exciplex, and
a difference between a HOMO energy level and a LUMO energy level of the exciplex (ΔEexciplex) is greater than a difference between a HOMO energy level and a LUMO energy level of the dopant (ΔEdopant),
wherein the first compound and the second compound are each independently selected from compounds represented by Formulae 1 to 3 and 301:

OG Complex Work Unit Chemistry
in Formulae 1 to 3,
X11 is O, S, N[(L11)a11—(R11)b11], C(R11a)(R11b), or Si(R11a)(R11b),
X21 is O, S, N[(L21)a21—(R21)b21], C(R21a)(R21b), or Si(R21a)(R21b),
Y1 to Y8 are each independently N or C(R14), wherein, when C(R14) is 2 or more, two or more R14(s) are identical to or different from each other,
Y11 to Y18 are each independently N or C(R24), wherein, when C(R24) is 2 or more, two or more R24(s) are identical to or different from each other,
CY1 is a group represented by Formula 2A, and CY2 is a group represented by Formula 2B,

OG Complex Work Unit Chemistry
in Formula 2A, C* and C** are each a carbon condensed with an X21-containing 5-membered ring,
in Formula 2A, Y19 to Y22 are each independently N, C, or C(R25), wherein, when C(R25) is 2 or more, two or more of R25(s) are identical to or different from each other, and two adjacent among Y19 to Y22 are each a carbon condensed with an X22-containing 5-membered ring,
in Formula 2B, X22 is O, S, N[(L24)a24—(R26)b26], C(R26a)(R26b), or Si(R26a)(R26b),
L11 to L13, L21 to L24, and L31 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
a11 to a13, a21 to a24, and a31 are each independently an integer from 0 to 5,
R11 to R14, R11a, R11b, R21 to R26, R21a, R21b, R26a, R26b, R31, and R32 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 C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
two adjacent groups among R11 to R14, R11a, and R11b are optionally linked together via a linking group selected from a single bond, *—O—*, *—S—*, *—B(R15)—*′, *—N(R15)—*′, *—C(R15)(R16)—*′, *—C(R15)═C(R16)—*′, a C5-C30 carbocyclic group, and a C1-C30 heterocyclic group,
two adjacent groups among R21 to R26, R21a, R21b, R26a, and R26b are optionally linked together via a linking group selected from a single bond, *—O—*′, *—S—*′, *—B(R27)—*′, *—N(R27)—*′, *—C(R27)(R28)—*′, —C(R27)═C(R28)—*′, a C5-C30 carbocyclic group, and a C1-C30 heterocyclic group,
R15, R16, R27, and R28 are each independently selected from: hydrogen, a C1-C20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, a C1-C20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
b11 to b13, b21 to b23, b26, b31, and b32 are each independently an integer from 1 to 5,
n1, n2, n21, and n22 are each independently an integer from 1 to 4, and
n31 is an integer from 1 to 3,
wherein in Formula 301,
Ar301 is selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
xb11 is an integer from 1 to 3,
L301 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
xb1 is an integer from 0 to 5,
R301 is 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 C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q301)(Q302)(Q303), —N(Q301)(Q302), —B(Q301)(Q302), —C(═O)(Q301), —S(═O)2(Q301), and —P(═O)(Q301)(Q302),
xb21 is an integer from 1 to 5, and
Q301 to Q303 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.