IP Library › Granted Patent US 11,575,092
Granted Patent B2
US 11,575,092 · App. 16/923,539 · Granted Feb 7, 2023

Organic light-emitting device and apparatus including the same

Inventors: Hyunyoung Kim (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); Youngeun Choi (Yongin-si, KR); Jaejin Lyu (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0085H01L51/008H01L51/0087H01L51/4273H01L51/5056H01L51/5072H01L51/5092
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Quick Facts
Patent No.
US 11,575,092
App. No.
16/923,539
Granted
Feb 7, 2023
Kind
B2
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 Formula 4, each as respectively described in the detailed description.

Claims (128)

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 Formula 4; 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 1 ), 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 that is 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 that is 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 independently selected from a single bond, *—O—*′, *—S*′, *—C(R 37 )(R 38 )—*′, *—Si(R 37 )(R 38 )—*′, *—B(R 37 )—*′, *—N(R 37 )—*′, and *—P(R 37 )—*′,

* 1 , * 2 , * 3 , and * 4 each indicate a binding site to M 31 ,

R 31 to R 38 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic 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 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ), wherein R 31 to R 38 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group, and

b31 to b34 are each independently an integer from 0 to 10,

wherein in Formula 4,

X 41 is N, B, P(═O)(R 44 ), or P(═S)(R 44 ),

Y 41 to Y 43 are each independently O, S, N(R 45 ), B(R 45 ), C(R 45 )(R 46 ), or Si(R 45 )(R 46 ),

k41 is 0 or 1, and when k41 is 0, —(Y 41 ) k41 — does not exist,

A 41 to A 43 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group,

R 41 to R 46 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic 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 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ), wherein R 41 to R 46 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, and

b41 to b43 are each independently an integer from 0 to 10,

wherein in Formulae 1, 2A, 2B, 3 and 4,

Q 1 to Q 3 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

2. The organic light-emitting device of claim 1 , wherein:

the first compound is selected from compounds of Group I;

the second compound is selected from compounds of Group II,

the third compound is selected from compounds of Groups III-I and III-II, and

the fourth compound is selected from compounds of Group IV:

3. The organic light-emitting device of claim 1 , wherein the second compound is represented by Formula 2-1 or Formula 2-2:

wherein, in Formulae 2-1 and 2-2,

X 21 is selected from O, S, N(R 24 ), and C(R 24 )(R 25 ),

R 21a to R 21c , R 22a to R 22d , R 23a to R 23e , R 24 , and 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 ),

at least one selected from R 21a to R 21c , R 22a to R 22d , R 24 , and R 25 in Formula 2-1 is the group represented by *-(L 21 ) a21 -A 21 ,

at least one selected from R 23a to R 23e in Formula 2-2 is the group represented by *-(L 21 ) a21 -A 21 , and

b41 to b43 are each independently an integer from 0 to 10,

wherein Q 1 to Q 3 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

4. The organic light-emitting device of claim 1 , wherein A 21 is selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, and a quinazolinyl group,

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, and a quinazolinyl group, each substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl 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 phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, and a quinazolinyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, and a quinazolinyl group that are each independently substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl 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 ).

5. The organic light-emitting device of claim 1 , wherein A 11 is selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, and a dinaphthothiophenyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, and a dinaphthothiophenyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl 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 phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, and a dinaphthothiophenyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, and a dinaphthothiophenyl group that are each independently substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, a triphenylenyl group, a chrysenyl group, a fluoranthenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzofluorenyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a dibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl 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 ).

6. The organic light-emitting device of claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region between the first electrode and the emission layer and/or an electron transport region between the emission layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, and/or an electron blocking layer, and

the electron transport region comprises a hole blocking layer, an electron transport layer, and/or an electron injection layer.

7. The organic light-emitting device of claim 6 , wherein the hole blocking layer comprises a hole blocking material represented by Formula 10:

wherein, in Formula 10,

L 101 to L 103 are each independently selected from a substituted or unsubstituted C 5 -C 30 carbocyclic group and a substituted or unsubstituted C 1 -C 30 heterocyclic group,

a101 to a103 are each independently selected from 0, 1, and 2, and

R 101 to R 103 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic 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 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ).

8. The organic light-emitting device of claim 1 , wherein A 11 is represented by one of Formulae 8-1 to 8-5:

wherein, in Formulae 8-1 to 8-5,

X 81 is selected from O, S, N(R 89 ), and C(R 89 )(R 90 ),

R 81 to R 90 are each independently selected from hydrogen, deuterium, a C 1 -C 20 alkyl group, a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and

* indicates a binding site to a neighboring atom.

9. The organic light-emitting device of claim 1 , wherein the third compound is represented by Formula 3-1 or Formula 3-2:

wherein, in Formulae 3-1 and 3-2,

X 31 to X 40 are each independently selected from N and C, and

M 31 , A 31 to A 34 , R 32 to R 34 , b32 to b34, Y 31 to Y 34 , T 31 to T 33 , k31 to k33, L 32 , n31 and n32 are each the same as respectively defined in connection with Formula 3.

10. An apparatus comprising:

a thin-film transistor comprising a source electrode, a drain electrode, and an activation layer; and

the organic light-emitting device of claim 1 ,

wherein the first electrode of the organic light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.

11. The organic light-emitting device of claim 1 , wherein the first compound is represented by one of Formulae 1-1 to 1-5:

wherein, in Formulae 1-1 to 1-5,

L 11 , a11, A 11 , and R 11 to R 19 are each the same as respectively defined in connection with Formula 1.

12. The organic light-emitting device of claim 1 , wherein the fourth compound is represented by Formula 4-11 or Formula 4-12:

wherein, in Formulae 4-11 and 4-12,

R 41a to R 41d , R 42a to R 42d , R 43a to R 43c , R 44a to R 44d , R 45a , R 45b , and R 46a to R 46c are each the same as respectively defined in connection with R 41 in Formula 4.

13. The organic light-emitting device of claim 1 , wherein the fourth compound is represented by Formula 4-1:

14. The organic light-emitting device of claim 1 , wherein:

at least one of R 21 , R 22 , R 24 and R 25 in Formula 2A is the group represented by *-(L 21 ) a21 -A 21 , and

at least one R 23 out of a number (6-k23) in Formula 2B is the group represented by *-(L 21 ) a21 -A 21 .

15. The organic light-emitting device of claim 1 , wherein a ratio of a light emitted from the fourth compound to a total light emitted from the emission layer is 80% or more.

16. The organic light-emitting device of claim 1 , wherein the first compound, the second compound, and the third compound are substantially not to emit light.

17. The organic light-emitting device of claim 1 , wherein at least one of R 11 to R 19 is represented by *-(L 11 ) a11 -A 11 .

18. The organic light-emitting device of claim 1 , wherein the fourth compound is to emit light.

19. The organic light-emitting device of claim 1 , wherein X 41 is N or B.

20. The organic light-emitting device of claim 1 , wherein X 11 is N(R 19 ).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 8, 2020
From: KIM, HYUNYOUNG; KIM, MINJE; KIM, EUNGDO; KIM, HYOJEONG; SHIN, HYOSUP; YOON, SEOKGYU; LEE, YOUNGKI; LEE, JUNGSUB; LEE, JIYOUNG; JUNG, HYEJIN; CHO, KUNWOOK; CHO, HYEONGU; CHOI, MINSOO; CHOI, YOUNGEUN; LYU, JAEJIN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 053151/0267 →
Priority Claims (1)
KR 10-2019-0123352 · Oct 4, 2019 · national
Continuity (1)
Related Publication 20210104689A1 · Apr 8, 2021