Organic light-emitting device and apparatus including the same

Patent metadata

Field	Value
Publication number	US-11793065-B2
Application number	US-202016865180-A
Country	US
Kind code	B2
Filing date	May 1, 2020
Priority date	Oct 4, 2019
Publication date	Oct 17, 2023
Grant date	Oct 17, 2023

Abstract

An organic light-emitting device and an apparatus including the same are disclosed. The organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode. The organic layer includes an emission layer, the emission layer includes 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, each as respectively described in the detailed description.

First claim

What is claimed is:

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:

wherein in Formula 1, X 11 is selected from O, S, N(R 19 ), and C(R 19 )(R 20 );
R 11 to R 20 are each independently selected from:
a group represented by *-(L 11 ) a11 -A 11 , hydrogen, deuterium, a C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), and —N(Q 1 )(Q 2 );
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), and —N(Q 31 )(Q 32 ); 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 21 )(Q 22 )(Q 23 ), —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 21 )(Q 22 ), and —N(Q 21 )(Q 22 ), L 11 is selected from:
a π electron-depleted nitrogen-free cyclic group, —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, and —N(Q 1 )-; and
a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), and —N(Q 31 )(Q 32 ),

a11 is selected from 1, 2, and 3, and
A 11 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), and —N(Q 31 )(Q 32 ); 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —C(Q 21 )(Q 22 )(Q 23 ), —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 21 )(Q 22 ), and —N(Q 21 )(Q 22 ), wherein in Formulae 2A and 2B,

X 21 is selected from O, S, N(R 24 ), and C(R 24 )(R 25 ),
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,
R 21 to R 25 are each independently selected from:
a group represented by *-(L 21 ) a21 -A 21 , hydrogen, deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 );
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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 ); 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 21 )(Q 22 )(Q 23 ), —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 21 )(Q 22 ), —N(Q 21 )(Q 22 ), —S(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), and —P(═S) (Q 21 )(Q 22 ), L 21 is selected from:
a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, —N(Q 1 )-, —S(═O)—, —S(═O) 2 —, —P(═O)(Q 1 )-, and —P(═S)(Q 1 )-; 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 );

a21 is selected from 1, 2, and 3, and
A 21 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), —N(Q 31 )(Q 32 ), —S(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(═O)(Q 31 )(Q 32 ), and —P(═S)(Q 31 )(Q 32 ); 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 C 1 -C 60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, a π electron-depleted nitrogen-free cyclic group, —C(Q 21 )(Q 22 )(Q 23 ), —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 21 )(Q 22 ), —N(Q 21 )(Q 22 ), —S(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), and —P(═S)(Q 21 )(Q 22 ), wherein in Formula 3,

M 31 is selected from transition metals of Period 4, Period 5, and Period 6 of the Periodic Table of Elements,
L 31 is a ligand represented by one selected from Formulae 3A to 3D,
L 32 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,
A 31 to A 34 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group,
T 31 to T 34 are each independently selected from a single bond, a double bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R 35 )(R 36 )—*′, *—C(R 35 )═C(R 36 )—*′, *—C(R 35 )═*′, *—Si(R 35 )(R 36 )—*′, *—B(R 35 )*′, *—N(R 35 )—*′, and *—P(R 35 )—*′,
k31 to k34 are each independently selected from 1, 2, and 3,
Y 31 to Y 34 are each independe

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Hyunyoung
• Choi Youngeun
• Kim Minje
• Kim Eungdo
• Kim Hyojeong
• Shin Hyosup
• Yoon Seokgyu
• Lee Youngki
• Lee Jungsub
• Lee Jiyoung
• Jung Hyejin
• Cho Kunwook
• Cho Hyeongu
• Choi Minsoo
• Lyu Jaejin

Classifications

• H10K59/871

  Self-supporting sealing arrangements · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K85/342 Primary

  comprising iridium · CPC title

• H10K85/631 Primary

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title