Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12398317-B2
Application number	US-201916713406-A
Country	US
Kind code	B2
Filing date	Dec 13, 2019
Priority date	Dec 17, 2018
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

Provided are an organometallic compound and an organic light-emitting device including the same. An organic layer of the organic light-emitting device includes an organometallic compound represented by Formula 1:

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 and comprising an emission layer,
wherein the organic layer comprises an organometallic compound represented by Formula 1:

wherein, in Formula 1,
M 11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
Y 10 , Y 20 , Y 30 , and Y 40 are each independently N or C,
Y 11 , Y 12 , Y 21 , Y 22 , Y 31 , Y 32 , Y 41 , and Y 42 are each independently N or C, A 30 , and A 40 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
T 11 to T 14 are each independently selected from a single bond, *—O—*′, and *—S—*′,
L 11 is selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, *—O—*′, *—S—*, *—C(R 1 )(R 2 )—*, *—C(R 1 )═*, *═C(R 1 )—*, *—C(R 1 )═C(R 2 )—*, *—C(═O)—*′, *—C(═S)—*, *—C≡C—*, *—B(R 1 )—*′, *—N(R 1 )—*′, *—P(R 1 )—*, *—Si(R 1 )(R 2 )—*, *—P(R 1 )(R 2 )—*, and *—Ge(R 1 )(R 2 )—*′,
a11 is selected from 1, 2, 3, 4, and 5,
at least one selected from L 11 (s) in the number of a11 is a substituted or unsubstituted C 3 -C 10 cycloalkylene group,
L 12 and L 14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 1 )(R 2 )—*′, *—C(R 1 )═*, *═C(R 1 )—*′, *—C(R 1 )═C(R 2 )—*′, *—C(═O)—*, *—C(═S)—*, *—C≡C—*, * B(R 1 )—*, *—N(R 1 )—*′, *—P(R 1 )—*, *—Si(R 1 )(R 2 )—*, *—P(R 1 )(R 2 )—*′, and *—Ge(R 1 )(R 2 )—*,
L 13 is selected from a single bond, *—O—*′, *—S—*′, *—B(R 1 )—*′, *—N(R 1 )—*′, *—P(R 1 )—*′, *—P(R 1 )(R 2 )—*′, and *—Ge(R 1 )(R 2 )—*′, wherein, if L 11 is a cyclohexylene group, L 13 is *—B(R 1 )—*′,
a12, and a14 are each independently selected from 0, 1, 2, 3, 4, and 5,
a13 is selected from 1, 2, 3, 4, and 5,
R 1 , R 2 , R 10 , R 20 , R 30 , and R 40 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 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 C 1 -C 60 hetero aryloxy group, a substituted or unsubstituted C 1 -C 60 hetero arylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —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 ),
R 1 and R 2 are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
R 1 and R 10 ; R 1 and R 20 ; R 1 and R 30 ; or R 1 and R 40 are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
b10, b20, b30, and b40 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
* and *′ each indicate a binding site to a neighboring atom,
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 3 -C 10 cycloalkylene group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 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 amidino group, a hydrazino group, a hydrazono 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cya

Assignees

• Samsung Display Co Ltd

Inventors

• HAN Junghoon
• Ko Soobyung
• Kim Sungbum
• Shin Sujin
• Ahn Eunsoo
• Lee Jaesung
• Jeon Mina
• Kim Youngkook

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/361

  Polynuclear complexes, i.e. complexes comprising two or more metal centers · CPC title