US 11,944,003 B2
Organic light-emitting device
Myeongsuk Kim, Yongin-si (KR); Sungwook Kim, Yongin-si (KR); Wonjun Song, Yongin-si (KR); Jinsoo Hwang, Yongin-si (KR); and Changwoong Chu, Yongin-si (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on May 6, 2021, as Appl. No. 17/313,493.
Application 17/313,493 is a continuation of application No. 16/861,571, filed on Apr. 29, 2020, granted, now 11,018,304.
Application 16/861,571 is a continuation in part of application No. 15/365,522, filed on Nov. 30, 2016, granted, now 10,665,789, issued on May 26, 2020.
Claims priority of application No. 10-2015-0169272 (KR), filed on Nov. 30, 2015.
Prior Publication US 2021/0336144 A1, Oct. 28, 2021
Int. Cl. H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 59/35 (2023.01)
CPC H10K 85/633 (2023.02) [H10K 85/636 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 59/35 (2023.02); H10K 85/615 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/6572 (2023.02)] 16 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, wherein
the first electrodes an anode,
the second electrode is a cathode,
the organic layer comprises:
first compound;
a second compound;
an emission layer; and
an emission auxiliary layer between the first electrode and the emission layer,
the first compound is comprised in the emission auxiliary layer,
the second compound is comprised in the emission layer,
the emission auxiliary layer and the emission layer directly contact each other,
the first compound is represented by one selected from Formulae 1A and 1B, and
the second compound is represented by Formula 2A:

OG Complex Work Unit Chemistry
wherein, in Formulae 1A, 1B, 2A, and 10,
A21 is a group represented by Formula 10,
m21 is an integer from 1 to 3,
X1 is O or S,
X2 is selected from a single bond, O, and S,
ring B1 and ring B2 are each independently selected from benzene and naphthalene, provided that ring B1 and ring B2 are not simultaneously a benzene group,
L1 to L12, L21, and L22 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,
a1 to a12, a21, and a22 are each independently an integer from 0 to 3,
Ar1 to Ar8, and Ar21 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 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,
b1 to b8, and b21 are each independently an integer from 1 to 5,
Ar1 and Ar2 are optionally linked to form a saturated or unsaturated ring, Ara and Ar4 are optionally linked to form a saturated or unsaturated ring, Ar5 and Ar6 are optionally linked to form a saturated or unsaturated ring, and Ar7 and Ar8 are optionally linked to form a saturated or unsaturated ring,
R1 to R8, R21, R51, and R52 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, and —Si(Q1)(Q2)(Q3),
c1 to c4, c7, and c8 are each independently an integer from 0 to 4, c5 and c6 are each independently an integer from 0 to 5, c21 is an integer from 0 to 8, and c51 and c52 are each independently an integer from 0 to 6,
n1 to n4, n7, and n8 are each independently an integer from 0 to 4, and n5 and n6 are each independently an integer from 0 to 5, provided that the sum of n1, n2, n3, and n4 is one or more and the sum of n5, n6, n7, and n8 is one or more,
n21 is an integer from 1 to 3, and
at least one substituent selected from a substituent(s) of the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), and —N(Q14)(Q15);
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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with a least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), and —N(Q24)(Q25); and
—Si(Q31)(Q32)(Q33) and —N(Q34)(Q35),
wherein Q1 to Q3, Q11 to Q15, Q21 to Q25, and Q31 to Q35 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 hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, and
* indicates a binding site to a neighboring atom.