IP Library › Granted Patent US 11,171,296
Granted Patent B2
US 11,171,296 · App. 16/207,027 · Granted Nov 9, 2021

Organometallic compound, organic light-emitting device including the same, and organic light-emitting apparatus including the organic light-emitting device

Inventors: Munki Sim (Yongin-si, KR); Soobyung Ko (Yongin-si, KR); Sungbum Kim (Yongin-si, KR); Junha Park (Yongin-si, KR); Heechoon Ahn (Yongin-si, KR); Hyoyoung Lee (Yongin-si, KR); Mina Jeon (Yongin-si, KR); Mieun Jun (Yongin-si, KR); Junghoon Han (Yongin-si, KR); Youngkook Kim (Yongin-si, KR); Seokhwan Hwang (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H01L51/0087C07F15/0086H01L27/3244H01L51/5016H01L51/5056H01L51/5072H01L51/5088H01L51/5092H01L51/5096
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Quick Facts
Patent No.
US 11,171,296
App. No.
16/207,027
Granted
Nov 9, 2021
Kind
B2
Abstract

Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises at least one of the organometallic compound represented by Formula 1.

Claims (126)

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 and comprising an emission layer,

wherein the organic layer comprises at least one of the organometallic compound represented by Formula 1:

wherein, in Formula 1,

M is selected from transition metals,

CY 1 and CY 2 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

X 1 is C(R 11 ) or N, X 2 is C(R 12 ) or N, X 3 is C(R 13 ) or N, and X 4 is C(R 14 ) or N,

Y 1 and Y 2 are each independently C or N,

a bond between Y 1 and M and a bond between Y 2 and M are each a coordinate bond,

A is selected from O, S, N(R 3 ), C(R 3 )(R 4 ), and Si(R 3 )(R 4 ),

T 1 and T 2 are each independently selected from *—O—*′, *—S—*′, *—C(R 5 )(R 6 )—*′, *—C(R 5 )=*′, *=—C(R 5 )*′, *—C(R 5 )=C(R 6 )—*′, *—C(=O)—*′, *—C(=S)—*′, *—C≡C—*′, *—B(R 5 )—*′, *—N(R 5 )—*′, *—P(R 5 )—*′, *—Si(R 5 )(R 6 )—*′, *—P(R 5 )(R 6 )—*′, and *—Ge(R 5 )(R 6 )—*′,

T 3 is a single bond,

R 1 to R 6 and R 11 to R 14 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(=O)(Q 1 ), —S(=O) 2 (Q 1 ), and —P(=O)(Q 1 )(Q 2 ), wherein two neighboring groups selected from R 1 to R 6 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,

a1 and a2 are each independently an integer of 1 to 5, wherein, when a1 is two or more, two or more R 1 (s) are identical to or different from each other, and when a2 is two or more, two or more R 2 (s) are identical to or different from each other,

at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic 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 C 1 -C 60 hetero aryloxy group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

deuterium (—D), —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 10 -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 ),

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 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and

* and *′ each indicate a binding site to a neighboring atom.

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

the first electrode is an anode,

the second electrode is a cathode,

the organic layer comprises: i) a hole transport region between the first electrode and the emission layer and comprising a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any combination thereof, and ii) an electron transport region between the emission layer and the second electrode and comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

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

the emission layer comprises the organometallic compound,

the organometallic compound in the emission layer serves as a phosphorescent dopant such that phosphorescence is emitted from the emission layer; or

the organometallic compound in the emission layer serves as a delayed fluorescent dopant such that delayed fluorescence is emitted from the emission layer.

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

the emission layer consists of the organometallic compound; or

the emission layer further comprises a host, and an amount of the organometallic compound in the emission layer is in a range of about 0.01 parts by weight to about 50 parts by weight based on 100 parts by weight of the emission layer.

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

the emission layer comprises at least one of a pyrene-containing compound, an arylamine-based compound, and a styryl-based compound.

6. An electronic apparatus comprising:

a thin film transistor; and

the organic light-emitting device of claim 1 ,

wherein the thin film transistor comprises a source electrode, a drain electrode, an active layer, and a gate electrode, and

the first electrode of the organic light-emitting device is electrically coupled to one of the source electrode and the drain electrode of the thin film transistor.

7. An organometallic compound represented by Formula 1:

wherein, in Formula 1,

M is selected from transition metals,

CY 1 and CY 2 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

X 1 is C(R 11 ) or N, X 2 is C(R 12 ) or N, X 3 is C(R 13 ) or N, and X 4 is C(R 14 ) or N,

Y 1 and Y 2 are each independently C or N,

a bond between Y 1 and M and a bond between Y 2 and M are each a coordinate bond,

A is selected from O, S, N(R 3 ), C(R 3 )(R 4 ), and Si(R 3 )(R 4 ),

T 1 and T 2 are each independently selected from *—O—*′, *—S—* ′, *—C(R 5 )(R 6 )—*′, *—C(R 5 )=*′, *=C(R 5 )—*′, *—C(R 5 )=C(R 6 )—*′, *—C(=O)—*′, *—C(=S)—*′, *—C≡C—*′, *—B(R 5 )—*′, *—N(R 5 )—*′, *—P(R 5 )—*′, *—Si(R 5 )(R 6 )—*′, *—P(R 5 )(R 6 )—*′, and *—Ge(R 5 )(R 6 )—*′,

T 3 is a single bond,

R 1 to R 6 and R 11 to R 14 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(=O)(Q 1 ), —S(=O) 2 (Q 1 ), and —P(=O)(Q 1 )(Q 2 ), wherein two neighboring groups selected from R 1 to R 6 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,

a1 and a2 are each independently an integer of 1 to 5, wherein, when a1 is two or more, two or more R 1 (s) are identical to or different from each other, and when a2 is two or more, two or more R 2 (s) are identical to or different from each other,

at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic 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 C 1 -C 60 hetero aryloxy group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

deuterium (—D), —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 ),

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 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and

* and *′ each indicate a binding site to a neighboring atom.

8. The organometallic compound of claim 7 , wherein:

M is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), and osmium (Os).

9. The organometallic compound of claim 7 , wherein:

CY 1 and CY 2 are each independently selected from:

a 5-membered carbocyclic group, a 6-membered carbocyclic group, a 5-membered heterocyclic group, and a 6-membered heterocyclic group; and

a condensed ring in which two or more groups selected from a 5-membered carbocyclic group, a 6-membered carbocyclic group, a 5-membered heterocyclic group, and a 6-membered heterocyclic group are condensed.

10. The organometallic compound of claim 7 , wherein:

a moiety represented by

in Formula 1 is selected from groups represented by Formulae 3-1 to 3-40:

wherein Z 31 to Z 32 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 C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group,

d2 is an integer of 0 to 2,

d3 is an integer of 0 to 3,

d4 is an integer of 0 to 4,

d6 is an integer of 0 to 6, and

* indicates a binding site to M in Formula 1, and *′indicates a binding site to a neighboring group.

11. The organometallic compound of claim 7 , wherein:

a moiety represented by

in Formula 1 is selected from groups represented by Formulae 4-1 to 4-40:

wherein Z 41 to Z 42 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 C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group,

e2 is an integer of 0 to 2,

e3 is an integer of 0 to 3,

e4 is an integer of 0 to 4,

e6 is an integer of 0 to 6, and,

* indicates a binding site to M in Formula 1, and *′ indicates a binding site to a neighboring group.

12. The organometallic compound of claim 7 , wherein:

X 1 is C(R 11 ), X 2 is C(R 12 ), X 3 is C(R 13 ), and X 4 is C(R 14 ), to R 14 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 C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group.

13. The organometallic compound of claim 7 , wherein:

Y 1 and Y 2 are each N.

14. The organometallic compound of claim 7 , wherein:

T 1 and T 2 and are each independently selected from *—O—*′, *—S—*′, *—C(R 7 )(R 8 ) —*′, —B(R 7 )—*′, *—N(R 7 )—*′, *—P(R 7 )—*′, *—Si(R 7 )(R 8 )—*′, and *—P(R 7 )(R 8 )—*′.

15. The organometallic compound of claim 14 , wherein:

T 1 and T 2 are identical to each other.

16. The organometallic compound of claim 7 , wherein:

R 1 to R 6 and R 11 to R 14 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 C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

a C 1 -C 20 alkyl group and a C 1 -C 20 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 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;

a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group; and

a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl 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 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, —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

—Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(=O)(Q 1 ), —S(=O) 2 (Q 1 ), and —P(=O)(Q 1 )(Q 2 ), and

Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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 20 aryl group, a C 1 -C 20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

17. The organometallic compound of claim 7 , wherein:

Formula 1 is represented by Formula 1-1 or 1-2:

wherein, in Formulae 1-1 and 1-2, M, A, X 1 to X 4 , T 1 to T 3 , Y 1 , Y 2 , R 1 , R 2 , a1, and a2 are respectively the same as defined in claim 7 ,

CY 11 and CY 12 are respectively the same as defined in connection with CY 1 and CY 2 in claims 7 , and

X 5 is C(R 15 ) or N, and X 6 is C(R 16 ) or N.

18. The organometallic compound of claim 17 , wherein:

X 1 to X 4 is each CH,

T 3 is a single bond,

A is selected from O, S, N(R 3 ), C(R 3 )(R 4 ), and Si(R 3 )(R 4 ),

R 3 and R 4 are each independently selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 2 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group; and

a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, and a pyridazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group.

19. The organometallic compound of claim 7 , wherein:

Formula 1 is represented by one of Formulae 1-1 a to 1-1d:

wherein, in Formulae 1-1a to 1-1d, M, A, X 1 to X 4 , and T 1 to T 3 are respectively the same as defined in claim 7 .

X 11 is C(R 11a ) or N, X 12 is C(R 12a ) or N, X 13 is C(R 13a ) or N, X 14 is C(R 14a ) or N, X 15 is C(R 15a ) or N, X 16 is C(R 16a ) or N, X 17 is C(R 17a ) or N, and X 18 is C(R 18a ) or N,

R 11a to R 14a are respectively the same as defined in connection with R 1 in claim 7 , and R 15a to R 18a are respectively the same as defined in connection with R 2 in claim 7 ,

two neighboring groups selected from R 11a to R 18a 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,

X 21 is C(R 21a ) or N, X 22 is C(R 22a ) or N, X 23 is C(R 23a ) or N, and X 24 is C(R 24a ) or N,

X 31 is C(R 31a )(R 31b ) or N(R 31a ), and X 32 is C(R 32a )(R 32b ) or N(R 32a ),

R 21a , R 22a , R 31a , and R 31b are respectively the same as defined in connection with R 1 in claims 7 , and R 23a , R 24a , R 32a , and R 32b are respectively the same as defined in connection with R 2 in claim 7 , and

two neighboring groups selected from R 21a to R 24a , R 31a , R 31b , R 32a , and R 32b 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.

20. The organometallic compound of claim 7 , wherein:

the compound represented by Formula 1 is selected from Compounds 1 to 107:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 30, 2018
From: SIM, MUNKI; KO, SOOBYUNG; KIM, SUNGBUM; PARK, JUNHA; AHN, HEECHOON; LEE, HYOYOUNG; JEON, MINA; JUN, MIEUN; HAN, JUNGHOON; KIM, YOUNGKOOK; HWANG, SEOKHWAN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 047646/0436 →
Priority Claims (1)
KR 10-2018-0033483 · Mar 22, 2018 · national
Continuity (1)
Related Publication 20190296253A1 · Sep 26, 2019
Cited By (1)
US 12,557,544