US 12,289,987 B2
Organic light-emitting device and apparatus including the same
Jaeweon Hur, Yongin-si (KR); Kyungsik Kim, Yongin-si (KR); Sungwook Kim, Yongin-si (KR); Seulong Kim, Yongin-si (KR); Seungjin Chu, Yongin-si (KR); and Hyein Jeong, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Jul. 21, 2020, as Appl. No. 16/935,004.
Claims priority of application No. 10-2019-0176264 (KR), filed on Dec. 27, 2019.
Prior Publication US 2021/0202844 A1, Jul. 1, 2021
Int. Cl. H10K 85/60 (2023.01); C07D 209/88 (2006.01); C07F 7/08 (2006.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 85/40 (2023.01); H10K 101/30 (2023.01); H10K 101/40 (2023.01)
CPC H10K 85/633 (2023.02) [C07D 209/88 (2013.01); C07F 7/0812 (2013.01); H10K 85/40 (2023.02); H10K 85/636 (2023.02); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 50/18 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/6572 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 18 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, the organic layer comprising an emission layer and a hole transport region between the first electrode and the emission layer,
wherein the hole transport region comprises a first hole transport stack, a second hole transport stack between the first hole transport stack and the emission layer, and an electron blocking layer between the second hole transport stack and the emission layer,
the first hole transport stack comprises a first hole injection layer and a first hole transport layer,
the second hole transport stack comprises a second hole injection layer and a second hole transport layer,
the first hole injection layer is between the first electrode and the first hole transport layer,
the second hole injection layer is between the first hole transport layer and the second hole transport layer,
the first hole injection layer comprises a first compound,
the first hole transport layer comprises a second compound,
the second hole injection layer comprises a third compound,
the second hole transport layer comprises a fourth compound,
the electron blocking layer comprises a fifth compound,
the first compound, the second compound, the third compound, the fourth compound, and the fifth compound all are different from one another, and
the organic light-emitting device satisfies Equations 1 to 4:
HOMO(HTM1)≥HOMO(HTM2)   Equation 1
HOMO(HTM3)≥HOMO(HTM4)   Equation 2
HOMO(HTM1)−HOMO(HTM2)≤0.5 eV   Equation 3
HOMO(HTM3)−HOMO(HTM4)≤0.5 eV,   Equation 4
wherein in Equations 1 to 4, the HOMO(HTM1) is a lower energy level from among the HOMO energy level (eV) of the first compound and the HOMO energy level (eV) of the second compound,
the HOMO(HTM2) is a higher energy level from among the HOMO energy level (eV) of the third compound and the HOMO energy level (eV) of the fourth compound,
the HOMO(HTM3) is a lower energy level from among the HOMO energy level (eV) of the third compound and the HOMO energy level (eV) of the fourth compound, and
the HOMO(HTM4) is the HOMO energy level (eV) of the fifth compound,
wherein the fifth compound is a compound represented by Formula 5:

OG Complex Work Unit Chemistry
wherein, in Formula 5,
X51 is O or S,
L51 to L53 are each independently 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,
a51 to a53 are each independently an integer from 0 to 3, and
Ar51 and Ar52 are each independently selected from 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, and —Si(Q1)(Q2)(Q3),
where Q1 to Q3 are each an unsubstituted phenyl group, and
wherein at least one selected from among Ar51 and Ar52 is —Si(Q1) (Q2) (Q3),
b51 and b52 are each independently an integer from 1 to 5,
R51 and R52 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
c51 is an integer from 1 to 3, and
c52 is an integer from 1 to 4.