# US 10,370,588 B2 · Organometallic compound and organic light-emitting device including the same

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- Number: US 10,370,588 B2
- Document ID: US10370588B2
- Status: Granted
- Kind: B2
- Application number: 14/859,895
- Filed: 2015-09-21
- Published: 2016-06-30
- Granted: 2019-08-06
- Earliest claimed: 2014-12-30
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Jungin Lee; Yoonhyun Kwak; Sunyoung Lee; Ohyun Kwon; Seungyeon Kwak; Jiyoun Lee; Seokhwan Hong; Aram Jeon
- Web page: https://patentgrep.com/patent/US10370588B2

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0033: {Iridium compounds}
- C07F 15/0086: {Platinum compounds}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/342: {comprising iridium}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1096: containing other heteroatoms
- 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
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organometallic compound represented by Formula 1: M(L1)n1(L2)n2 Formula 1 wherein in Formula 1, M, L1, L2, n1, and n2 are the same as described in the specification.

## Claims

### Claim 1

An organometallic compound represented by Formula 1:
M(L1)n1(L2)n2 Formula 1
wherein M in Formula 1 is Ir;
L1 in Formula 1 is selected from ligands represented by Formulae 2A-1 to 2A-45, and n1 is 1, 2, or 3, wherein when n1 is 2 or more, 2 or more groups Li are identical to or different from each other;
L2 in Formula 1 is selected from organic ligands represented by Formulae 3-1(1) to 3-1(70), and n2 is 0, 1, or 2, wherein when n2 is or more, 2 or more groups L2 are identical to or different from each other;
n1+n2 is 3;
L1 and L2 in Formula 1 are different from each other;
wherein in Formulae 2A-1 to 2A-45,
* and *′ each indicates a binding site to M of Formula 1,
R11, R11a to R11c, R12 and R12a to R12c are each independently a deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, groups represented by Formulae 9-1 to 9-17, and groups represented by Formulae 10-7 to 10-30, and
R13, R13a, R13b, and R14 are each independently selected from groups represented by Formulae 2B(1) to 2B(18): and
* in Formulae 2B(1) to 2B(18) indicates a binding site to a neighboring atom; and
wherein in Formulae 3-1(1) to 3-1(70),
* and *′ each indicates a binding site to M of Formula 1,
Z1, Z2, Z1a, Z1b, Z1c, Z1d, Z2a, Z2b, Z2c, and Z2d are each independently selected from a deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —Si(Q3)(Q4)(Q5), groups represented by Formulae 9-1 to 9-17, and groups represented by Formulae 10-7 to 10-30,
wherein Q3 to Q5 are each independently selected from
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, and —CD2CDH2;
an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and
an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one of a deuterium and a C1-C10 alkyl group:
* in Formulae 9-1 to 9-17 and 10-1 to 10-30 indicates a binding site to a neighboring atom.

### Claim 2

An organometallic compound, comprising at least one of Compounds 1 to 8 and 10 to 73:

### Claim 3 (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 at least one organometallic compound of claim 1.

### Claim 4 (depends on 3)

The organic light-emitting device of claim 3, wherein the emission layer comprises the organometallic compound.