US 11,793,065 B2
Organic light-emitting device and apparatus including the same
Hyunyoung Kim, Yongin-si (KR); Youngeun Choi, Yongin-si (KR); Minje Kim, Yongin-si (KR); Eungdo Kim, Yongin-si (KR); Hyojeong Kim, Yongin-si (KR); Hyosup Shin, Yongin-si (KR); Seokgyu Yoon, Yongin-si (KR); Youngki Lee, Yongin-si (KR); Jungsub Lee, Yongin-si (KR); Jiyoung Lee, Yongin-si (KR); Hyejin Jung, Yongin-si (KR); Kunwook Cho, Yongin-si (KR); Hyeongu Cho, Yongin-si (KR); Minsoo Choi, Yongin-si (KR); and Jaejin Lyu, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on May 1, 2020, as Appl. No. 16/865,180.
Claims priority of application No. 10-2019-0123353 (KR), filed on Oct. 4, 2019.
Prior Publication US 2021/0104688 A1, Apr. 8, 2021
Int. Cl. H10K 85/30 (2023.01); H10K 50/11 (2023.01); H10K 50/18 (2023.01); H10K 50/12 (2023.01); H10K 50/84 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 101/00 (2023.01)
CPC H10K 85/342 (2023.02) [H10K 50/11 (2023.02); H10K 50/121 (2023.02); H10K 50/18 (2023.02); H10K 50/841 (2023.02); H10K 85/346 (2023.02); H10K 85/40 (2023.02); H10K 85/631 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 11/06 (2013.01); C09K 2211/1014 (2013.01); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 2101/90 (2023.02)] 20 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode,
wherein:
the organic layer comprises an emission layer,
the emission layer comprises a first compound, a second compound, a third compound, and a fourth compound,
the first compound is represented by Formula 1;
the second compound is represented by Formula 2A or Formula 2B;
the third compound is represented by Formula 3;
the fourth compound is represented by any one of Formulae 4-1 to 4-3; and
the first compound, the second compound, the third compound, and the fourth compound are different from each other:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein in Formula 1, X11 is selected from O, S, N(R19), and C(R19)(R20);
R11 to R20 are each independently selected from:
a group represented by *-(L11)a11-A11, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), and —N(Q1)(Q2);
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32); and
a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), and —N(Q21)(Q22), L11 is selected from:
a π electron-depleted nitrogen-free cyclic group, —C(Q1)(Q2)-, —Si(Q1)(Q2)-, —B(Q1)-, and —N(Q1)-; and
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32),
a11 is selected from 1, 2, and 3, and
A11 is selected from:
a π electron-depleted nitrogen-free cyclic group;
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32); and
a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), and —N(Q21)(Q22), wherein in Formulae 2A and 2B,
X21 is selected from O, S, N(R24), and C(R24)(R25),
k21 and k22 are each independently selected from 0, 1, 2, 3, and 4, wherein a sum of k21 and k22 is 1 or more,
k23 is selected from 1, 2, 3, 4, 5, and 6,
R21 to R25 are each independently selected from:
a group represented by *-(L21)a21-A21, hydrogen, deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2);
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), —N(Q31)(Q32), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), and —P(═S)(Q31)(Q32); and
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group that are each independently substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), —N(Q21)(Q22), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), and —P(═S) (Q21)(Q22), L21 is selected from:
a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q1)(Q2)-, —Si(Q1)(Q2)-, —B(Q1)-, —N(Q1)-, —S(═O)—, —S(═O)2—, —P(═O)(Q1)-, and —P(═S)(Q1)-; and
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), —N(Q31)(Q32), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), and —P(═S)(Q31)(Q32);
a21 is selected from 1, 2, and 3, and
A21 is selected from:
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group;
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), —N(Q31)(Q32), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), and —P(═S)(Q31)(Q32); and
a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from a π electron-depleted nitrogen-containing cyclic group and a π electron-depleted nitrogen-free cyclic group that are each independently substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), —N(Q21)(Q22), —S(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), and —P(═S)(Q21)(Q22), wherein in Formula 3,
M31 is selected from transition metals of Period 4, Period 5, and Period 6 of the Periodic Table of Elements,
L31 is a ligand represented by one selected from Formulae 3A to 3D,
L32 is selected from a monodentate ligand, a bidentate ligand, and a tridentate ligand,
n31 is 1 or 2, and
n32 is selected from 0, 1, 2, 3, and 4,
wherein in Formulae 3A to 3D,
A31 to A34 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
T31 to T34 are each independently selected from a single bond, a double bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R35)(R36)—*′, *—C(R35)═C(R36)—*′, *—C(R35)═*′, *—Si(R35)(R36)—*′, *—B(R35)*′, *—N(R35)—*′, and *—P(R35)—*′,
k31 to k34 are each independently selected from 1, 2, and 3,
Y31 to Y34 are each independently selected from a single bond, *—O—*′, *—S*′, *—C(R37)(R38)—*′, *—Si(R37)(R38)—*′, *—B(R37)—*′, *—N(R37)—*′, and *—P(R37)—*′,
*1, *2, *3, and *4 each indicate a binding site to M31,
R31 to R38 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, —C(Q1)(Q2)(Q3), —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2), wherein R31 to R38 are optionally linked to each other to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, and
b31 to b34 are each independently an integer from 0 to 10,
wherein in Formulae 4-1 to 4-3,
A41 and A42 are each independently selected from:
a π electron-depleted nitrogen-free cyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), and —N(Q1)(Q2);
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32); and
a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q21)(Q22)(Q23), —Si(Q21)(Q22)(Q23), —B(Q21)(Q22), and —N(Q21)(Q22),
m41 and m42 are each independently selected from 1, 2, and 3,
D41 and D42 are each independently selected from:
—F, a cyano group, a π electron-depleted nitrogen-containing cyclic group, a group containing C(═O), a group containing P(═O), and a group containing P(═S);
a π electron-depleted nitrogen-containing cyclic group, a group containing C(═O), a group containing P(═O), and a group containing P(═S), each substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group;
a π electron-depleted nitrogen-containing cyclic group, a group containing C(═O), a group containing P(═O), and a group containing P(═S), each substituted with at least one selected from a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group that are each independently substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group;
a C1-C60 alkyl group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group;
a C1-C60 alkyl group and a π electron-depleted nitrogen-free cyclic group, each substituted with a π electron-depleted nitrogen-containing cyclic group substituted with at least one selected from deuterium, —F, a cyano group, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group; and
a C1-C60 alkyl group and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from a C1-C60 alkyl group and a π electron-depleted nitrogen-free cyclic group that are each independently substituted with at least one selected from —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group,
n41 and n42 are each independently selected from 1, 2, and 3,
L41 and L42 are each independently selected from:
a π electron-depleted nitrogen-free cyclic group, —C(Q1)(Q2)-, —Si(Q1)(Q2)-, —B(Q1)-, and —N(Q1)-; and
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C1-C60 alkyl group, a π electron-depleted
nitrogen-free cyclic group, —C(Q31)(Q32)(Q33), —Si(Q31)(Q32)(Q33), —B(Q31)(Q32), and —N(Q31)(Q32), and
a41 and a42 are each independently selected from 0, 1, 2, and 3, and
wherein, in Formulae 1, 2A, 2B, 3, and 4-1 to 4-3,
Q1 to Q3, Q21 to Q23, and Q31 to Q33 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 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 C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
wherein A41 and D41 are different from each other.