# US 10,374,174 B2 · Organometallic compound and organic light-emitting device including the same

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- Number: US 10,374,174 B2
- Document ID: US10374174B2
- Status: Granted
- Kind: B2
- Application number: 14/931,270
- Filed: 2015-11-03
- Published: 2016-07-14
- Granted: 2019-08-06
- Earliest claimed: 2015-01-09
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Bumwoo Park; Yoonhyun Kwak; Hyun Koo; Jiwhan Kim; Sunyoung Lee; Jiyoun Lee
- Web page: https://patentgrep.com/patent/US10374174B2

## CPC

- H10K 85/346: {comprising platinum}
- C07F 15/0026: {without a metal-carbon linkage}
- C07F 15/004: {without a metal-carbon linkage}
- C07F 15/0093: {without a metal-carbon linkage}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/348: {comprising osmium}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

An organometallic compound represented by Formula 1: wherein in Formula 1, groups and variables are the same as described in the specification.

## Claims

### Claim 1

An organometallic compound represented by Formula 1:
wherein in Formula 1,
M is selected from a Period 1 transition metal, a Period 2 transition metal, and a Period 3 transition metal;
A11 to A13 are each independently selected from a C6-C20 cyclic group and a C1-C20 heterocyclic group; wherein A11 and Al2 are optionally linked to each other through a first linking group;
X11 to X13 are each independently N;
X14 is selected from N and P;
E11 to E14 are each independently a single bond;
Y11 to Y15 are each independently selected from a single bond and a divalent linking group; X14 and Y14 are linked together by a single bond or a double bond, and X14 and Y15 are linked together by a single bond or a double bond;
L11 is selected from a monodentate ligand and a bidentate ligand;
a11 is selected from 0, 1, and 2; and
R11 to R13 are each independently selected from a hydrogen, a 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 or a salt thereof, a phosphoric acid 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(═O)(Q1), —Si(Q1)(Q2)(Q3), and —N(Q1)(Q2);
wherein Q1 to Q3 are each independently selected from a C1-C60 alkyl group and a C6-C60 aryl group;
b11 to b13 are each independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10; and
at least one substituent of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from
a 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 C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a 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, and a phosphoric acid group or a salt thereof; and
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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

### Claim 2 (depends on 1)

The organometallic compound of claim 1, wherein
M is selected from Os, Ir, and Pt.

### Claim 3 (depends on 1)

The organometallic compound of claim 1, wherein
A11 to A13 are each independently selected from
a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, an oxadiazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, an indole, a benzoimidazole, a benzoxazole, an isobenzoxazole, an indazole, and a tetrahydroindazole; and
pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, an oxadiazole, a triazole, a pyridine, a pyrimidine, a pyrazine, a pyridazine, a triazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, an indole, a benzoimidazole, a benzoxazole, an isobenzoxazole, an indazole, and a tetrahydroindazole, each condensed with at least one selected from a C4-C10 alicyclic group and a C1-C10 heteroalicyclic group.

### Claim 4 (depends on 1)

The organometallic compound of claim 1, wherein
A11 is selected from groups represented by Formulae 2-5 to 2-8:
wherein in Formulae 2-5 to 2-8,
* is a binding site to M in Formula 1;
*′ is a binding site to Y11 or Y13; and
R21 to R25 each independently are the same as R11 in Formula 1.

### Claim 5 (depends on 1)

The organometallic compound of claim 1, wherein
A12 and A13 are each independently selected from groups represented by Formulae 3-4 to 3-9:
wherein in Formulae 3-4 to 3-9,
* is a binding site to M in Formula 1;
*′ is a binding site to Y11 or Y12; and
R31 to R40 each independently are the same as R12 and R13 in Formula 1.

### Claim 6 (depends on 1)

The organometallic compound of claim 1, wherein
X14 is N.

### Claim 7 (depends on 1)

The organometallic compound of claim 1, wherein
Y11 to Y15 are each independently selected from a single bond, a double bond, —O—, —S—, —{B(Q11)}-, —{N(Q12)}-, —{C(Q11)(Q12)}n11-, ═{C(Q11)}n1-, —{Si(Q11)(Q12)}n11-, —C(═O)—, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
wherein Q11 and Q12 are each independently selected from a hydrogen, a deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; and
n11 is selected from 1, 2, and 3.

### Claim 8 (depends on 1)

The organometallic compound of claim 1, wherein
Y11 to Y15 are each independently selected from a single bond, a double bond, —O—, —S—, —N(CH3)—, —N(Ph)-, —CH2—, —CH(CH3)—, —C(CH3)2—, —C(CH3)(Ph)-, —C(Ph)2-, ═C(CH3)—, ═C(Ph)-, —C(═O)—, and groups represented by Formulae 4-1 to 4-17:
wherein in Formulae 4-1 to 4-17,
each of * and *′ is a binding site to a neighboring atom.

### Claim 9 (depends on 1)

The organometallic compound of claim 1, wherein
Y11 to Y13 are each independently selected from a single bond, a double bond, —O—, —S—, —N(CH3)—, —N(Ph)-, —CH2—, —CH(CH3)—, —C(CH3)2—, and —C(═O)—.

### Claim 10 (depends on 1)

The organometallic compound of claim 1, wherein
Y14 and Y15 are each independently selected from a single bond, a double bond, —CH2—, ═C(CH3)—, ═C(Ph)-, and —C(═O)—.

### Claim 11 (depends on 1)

The organometallic compound of claim 1, wherein
L11 is selected from
I−, Br−, Cl−, a sulfide, a nitrate, an azide, a hydroxide, a cyanate, an isocyanate, a thiocyanate, water, an acetonitrile, a pyridine, an ammonia, a carbon monoxide, P(Ph)3, P(Ph)2CH3, PPh(CH3)2, and P(CH3)3; and
an oxalate, an acetylacetonate, a picolinic acid, a 1,2-bis(diphenylphosphino)ethane, a 1,1-bis(diphenylphosphino)methane, a glycinate, and an ethylenediamine.

### Claim 12 (depends on 1)

The organometallic compound of claim 1, wherein
R11 to R13 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, —CF3, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, —C(═O))(Q1), —Si(Q1)(Q2)(Q3), and —N(Q1)(Q2);
wherein Q1 to Q3 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, and a phenyl group.

### Claim 13 (depends on 1)

The organometallic compound of claim 1, wherein
R11 to R13 are each independently selected from a hydrogen, —F, a cyano group, a methyl group, an iso-propyl group, a tert-butyl group, —CF3, and —Si(CH3)3.

### Claim 14 (depends on 1)

The organometallic compound of claim 1, wherein
the organometallic compound is selected from groups represented by Formulae 1-1 to 1-3:
wherein in Formulae 1-1 to 1-3,
M, A11 to A13, Y11 to Y13, L11, a11, R11 to R13, and b11 to b13 are the same as defined in Formula 1; and
Q11 is selected from a hydrogen, a deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group.

### Claim 15 (depends on 1)

The organometallic compound of claim 1, wherein
the organometallic compound is represented by Formulae 1-11, 1-13, or 1-15:
wherein in Formula 1-11, 1-13, and 1-15,
M, A11 to A13, Y11, Y13, L11, a11, R11 to R13, and b11 to b13 are the same as defined in Formula 1; and
Q11 is selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, and a phenyl group.

### Claim 16 (depends on 1)

The organometallic compound of claim 1, wherein
the organometallic compound is represented by Formulae 1-21, 1-22, 1-26 to 1-28, 1-32 to 1-34, or 1-38:
wherein in Formulae 1-21, 1-22, 1-26 to 1-28, 1-32 to 1-34, and 1-38,
M, Al2, A13, Y11, Y13, L11, a11, R12, R13, b12, and b13 are the same as defined in Formula 1; and
Q11 is selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, and a phenyl group.

### Claim 17 (depends on 1)

The organometallic compound of claim 1, wherein
the organometallic compound is represented by Formulae 1-41, 1-42, 1-45, 1-46, 1-49, or 1-50:
wherein in Formulae 1-41, 1-42, 1-45, 1-46, 1-49 and 1-50,
M, Y11, Y13, L11, and a11 are the same as defined in Formula 1;
Q11 is selected from a hydrogen, a deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a tert-butyl group, and a phenyl group; and
Al2 and A13 are each independently selected from groups represented by Formulae 3-4 to 3-9;
wherein in Formulae 3-4 to 3-9,
* is a binding site to M;
*′ is a binding site to a neighboring atom; and
R31 to R40 are each independently selected from a hydrogen, —F, a cyano group, a methyl group, an iso-propyl group, a tert-butyl group, —CF3, and —Si(CH3)3.

### Claim 18 (depends on 1)

The organometallic compound of claim 1, wherein
the organometallic compound is selected from Compounds PD-1 to PD-6, PD-31 to PD-36, PD-46 to PD-48, and PD-51 to PD-64:

### Claim 19 (depends on 1)

An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, and
wherein the organic layer comprises the organometallic compound of claim 1.

### Claim 20 (depends on 1)

The organic light-emitting device of claim 1, wherein
the emission layer comprises the organometallic compound of claim 1.