US 11,903,310 B2
Organic light-emitting device and method of manufacturing the same
Hyoungkun Kim, Yongin-si (KR); Samil Kho, Yongin-si (KR); Donghwan Kim, Yongin-si (KR); Jinwoong Kim, Yongin-si (KR); Seunggak Yang, Yongin-si (KR); Kwanhee Lee, Yongin-si (KR); and Junyoung Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Jul. 31, 2020, as Appl. No. 16/945,444.
Claims priority of application No. 10-2019-0140323 (KR), filed on Nov. 5, 2019.
Prior Publication US 2021/0135124 A1, May 6, 2021
Int. Cl. H10K 85/00 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/81 (2023.01); H10K 101/30 (2023.01)
CPC H10K 85/6572 (2023.02) [H10K 85/615 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 50/15 (2023.02); H10K 50/156 (2023.02); H10K 50/81 (2023.02); H10K 2101/30 (2023.02)] 18 Claims
 
1. An organic light-emitting device comprising:
a first electrode having a work function greater than about 4.9 eV and less than about 5.2 eV;
a second electrode facing the first electrode;
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer;
a hole transport region disposed between the first electrode and the emission layer;
wherein the hole transport region comprises a first hole transport layer comprising a first hole-transporting material and a second transport layer disposed between the first hole transport layer and the emission layer;
the first hole transport layer is substantially free of a p-dopant,
the second hold transport layer comprises a second hole-transporting material different from the first hole-transporting material, and
the second hole-transporting material comprises a compound of Formula 202-2 below:

OG Complex Work Unit Chemistry
wherein in Formula 202-2,
L223 to L225 are each, independently from one another, 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 fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group;
xa23 to xa24 are each, independently from one another, an integer from 0 to 3;
xa25 is an integer from 1 to 10;
Ar223 to Ar224 are each, independently from one another, 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 fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group;
R221 and R222 are each, independently from one another, 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-Cia 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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1)(Q2), or —P(═O)(Q1)(Q2);
xb21 and xb22 are each, independently from one another, an integer from 1 to 4; and Q1 to Q3 are each, independently from one another, 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, or a terphenyl group.