IP Library › Granted Patent US 10,672,995

Granted Patent B2

US 10,672,995 · App. 14/801,080 · Granted Jun 2, 2020

Organometallic compound and organic light-emitting device including the same

Inventors: Rupasree Ragini Das (Suwon-si, KR); Kangmun Lee (Suwon-si, KR); Changho Noh (Suwon-si, KR); Hyejin Bae (Suwon-si, KR); Virendra Kumar Rai (Suwon-si, KR); Dmitry Kravchuk (Suwon-si, KR)

Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

H01L51/0085 C07F15/0033 C09K11/06 C09K2211/1007 C09K2211/1029 C09K2211/1044 C09K2211/1059 C09K2211/1074 C09K2211/185 H01L51/0059 H01L51/0067 H01L51/0072 H01L51/5016

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 10,672,995
App. No.: 14/801,080
Granted: Jun 2, 2020
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

An organometallic compound represented by Formula 1: Ir(L 1 ) n (L 2 ) (3-n) Formula 1 wherein in Formula 1, L 1 , L 2 , and n are the same as described in the specification.

Claims (191)

1. An organometallic compound represented by Formula 1:

wherein in Formulae 1 to 3,

L 1 is a first ligand represented by Formula 2;

L 2 is a second ligand represented by Formula 3, wherein L 2 includes at least one cyano group as a substituent;

n is selected from 2 and 3;

A 11 is selected from a C 6 -C 60 cyclic group and a C 1 -C 60 heterocyclic group selected from an imidazole, a pyrazole, an isothiazole, an isoxazole, a pyrazine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a benzoimidazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a pyridoindole, a pyridofuran, and a pyridothiophene, each comprising Y 11 as a cyclic ring member;

A 21 , and A 22 are each independently selected from a naphthalene, an anthracene, a phenanthrene, a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a benzoimidazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a pyridoindole, a pyridofuran, and a pyridothiophene;

Y 11 , Y 12 , Y 21 , and Y 22 are each independently selected from C and N;

X 13 is N or CR 13 ;

X 14 is N or CR 14 ;

X 15 is N or CR 15 ;

X 16 is N or CR 16 ;

X 17 is N or CR 17 ;

X 18 is N or CR 18 ;

X 19 is N or CR 19 ;

X 23 is N or CR 23 ; and

X 24 is N or CR 24 ;

provided that when A 11 is an imidazole, X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , X 17 is CR 17 , X 18 is CR 18 , and X 19 is CR 19 , then n in Formula 1 is 2, and the second ligand is represented by Formula 3A:

wherein in Formula 3A,

Y 21 and Y 22 are each independently selected from C and N;

X 21 is N or CR 21 , X 23 is N or CR 23 , and X 25 is N or CR 25 ;

provided that when Y 22 is C, then X 25 is N;

provided that when X 25 is C, then Y 22 is N;

R 21 to R 27 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, wherein at least one of R 21 to R 27 is a cyano group;

* and *′ are each independently a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, and —Si(Q 11 )(Q 12 )(Q 13 );

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy 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, and —Si(Q 21 )(Q 22 )(Q 23 ); and

—Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group;

wherein in Formula 2 and 3,

R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;

a11, a28, and a29 are each independently selected from 1, 2, 3, 4, 5, and 6;

R 12 and R 13 are optionally linked to each other via a divalent linking group selected from a single bond, *—O—*′, *—S—*′, *—N(Z 11 )—*′, and *—[C(Z 11 )(Z 12 )] b11 —*′; wherein

Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 1 -C 60 alkyl group, and a substituted or unsubstituted C 6 -C 60 aryl group;

b11 is selected from 1, 2, 3, and 4;

* and *′ are each independently a binding site to a neighboring atom;

a11 is selected from 1, 2, and 3;

* and *′ indicates a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

—Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and C 6 -C 60 aryl group.

2. The organometallic compound of claim 1 , wherein

L 1 comprises at least one cyano group as a substituent.

3. The organometallic compound of claim 1 , wherein

A 11 is selected from a benzene, a naphthalene, an anthracene, and a phenanthrene.

4. The organometallic compound of claim 1 , wherein A 11 is each independently selected from a benzene and a naphthalene.

5. The organometallic compound of claim 1 , wherein A 21 and A 22 are each independently selected from a naphthalene, a pyrrole, an imidazole, a pyrazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, a triazole, and a tetrazole.

6. The organometallic compound of claim 1 , wherein

Y 11 and Y 12 are different from each other, and Y 21 and Y 22 are different from each other.

7. The organometallic compound of claim 1 , wherein

R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group;

a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and

a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group, each substituted with at least one selected from a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

wherein Q 31 to Q 33 are each independently selected from a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, and a naphthyl group.

8. The organometallic compound of claim 1 , wherein

R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a phenyl group and a naphthyl group, each substituted with at least one selected from a deuterium, —F, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and

a phenyl group and a naphthyl group, each substituted with at least one selected from a phenyl group and a naphthyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

wherein Q 31 to Q 33 are each independently selected from a methyl group and a phenyl group.

9. The organometallic compound of claim 1 , wherein

R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, and any group selected from Formulae 6-1 to 6-13:

wherein in Formulae 6-1 to 6-13,

* indicates a binding site to a neighboring atom.

10. The organometallic compound of claim 1 , wherein

R 12 and R 13 are optionally linked to each other via a divalent linking group selected from a single bond,

and

Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, a methyl group, and an ethyl group.

11. The organometallic compound of claim 1 , wherein

the first ligand is represented by Formula 2A:

wherein in Formula 2A,

Y 11 and Y 12 are each independently selected from C and N;

X 13 is N or CR 13 , X 14 is N or CR 14 , and X 15 is N or CR 15 ;

R 11 to R 19 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;

a11 is selected from 1, 2, 3, 4, 5, and 6;

R 12 and R 13 are optionally linked to each other via a divalent linking group selected from a single bond, *—S—*′, *—N(Z 11 )—*′, and *—[C(Z 11 )(Z 12 )] b11 —*′; wherein

Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, and a substituted or unsubstituted C 1 -C 60 alkyl group;

b11 is selected from 1, 2, 3, and 4;

* and *′ are each independently a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group are selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

—Si(Q 31 )(Q 32 )(Q 33 );

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and C 6 -C 60 aryl group.

12. The organometallic compound as claimed in claim 11 , wherein

X 15 is CR 15 ; and

at least one group selected from R 11 and R 15 is a cyano group.

13. The organometallic compound as claimed in claim 1 , wherein

the first ligand is represented by any group selected from Formulae 2-1 to 2-10:

wherein in Formulae 2-1 to 2-10,

a11 is selected from 1, 2, 3, 4, 5, and 6;

Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, and a substituted or unsubstituted C 1 -C 60 alkyl group;

b11 is selected from 1, 2, 3, and 4;

* and *′ are each independently a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group are selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

—Si(Q 31 )(Q 32 )(Q 33 ),

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and C 6 -C 60 aryl group.

14. The organometallic compound as claimed in claim 1 , wherein

the second ligand is represented by Formula 3A:

wherein in Formula 3A,

Y 21 and Y 22 are each independently selected from C and N;

X 21 is N or CR 21 , X 23 is N or CR 23 , and X 25 is N or CR 25 ;

provided that when Y 22 is C, then X 25 is N;

provided that when X 25 is C, then Y 22 is N;

* and *′ are each independently a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group.

15. The organometallic compound as claimed in claim 1 , wherein

the second ligand is represented by Formula 3-1:

wherein in Formula 3-1;

X 21 is N or CR 21 ;

X 25 is N or CR 25 ,

R 21 , R 22 , and R 24 to R 27 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group, wherein at least one of R 21 , R 22 , and R 24 to R 27 is a cyano group;

a11 is selected from 1, 2, and 3;

* and *′ indicates a binding site to a neighboring atom.

16. 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 compounds of claim 1 .

17. The organic light-emitting device of claim 16 , wherein the emission layer comprises the organometallic compound of claim 1 .

18. The organometallic compound of claim 1 , wherein Y 12 is carbon.

19. An organometallic compound represented by any group selected from Formulae 1-2 to 1-4 and 1-6 to 1-8:

wherein in Formulae 1-2 to 1-4 and 1-6 to 1-8;

X 21 is N or CR 21 ; and X 25 is N;

R 11 to R 19 , R 21 , R 22 , R 24 , and R 27 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, wherein at least one of R 21 , R 22 , R 24 , and R 27 is a cyano group;

a11 is selected from 1, 2, and 3;

Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, a methyl group, and an ethyl group;

b11 is selected from 1 and 2;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

—Si(Q 31 )(Q 32 )(Q 33 );

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group.

20. An organometallic compound selected from Compounds 3 to 6, 8 to 11, 13, and 14:

21. An organometallic compound represented by

wherein in Formulae 1 to 3,

L 1 is a first ligand represented by Formula 2;

L 2 is a second ligand represented by Formula 3, wherein L 2 includes at least one cyano group as a substituent;

n is selected from 2 and 3;

A 11 is selected from a C 6 -C 60 cyclic group and a C 1 -C 60 heterocyclic group, each comprising Y 11 as a cyclic ring member;

Y 11 , Y 12 , Y 21 , and Y 22 are each independently selected from C and N;

X 13 is N or CR 13 ;

X 14 is N or CR 14 ;

X 15 is N or CR 15 ;

X 16 is N or CR 16 ;

X 17 is N or CR 17 ;

X 18 is N or CR 18 ;

X 19 is N or CR 19 ;

X 23 is N or CR 23 ; and

X 24 is N or CR 24 ;

wherein at least one selected from X 13 to X 19 is nitrogen;

provided that when Y 22 is C, then X 25 is N;

provided that when X 25 is C, then Y 22 is N;

a11, a28, and a29 are each independently selected from 1, 2, 3, 4, 5, and 6;

R 12 and R 13 are optionally linked to each other via a divalent linking group selected from a single bond, *—O—*′, *—S—*′, *—N(Z 11 )—*′, and *—[C(Z 11 )(Z 12 )] b11 —*′; wherein Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 1 -C 60 alkyl group, and a substituted or unsubstituted C 6 -C 60 aryl group;

b11 is selected from 1, 2, 3, and 4;

* and *′ are each independently a binding site to a neighboring atom;

a11 is selected from 1, 2, and 3;

* and *′ indicates a binding site to a neighboring atom;

at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from

a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;

a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;

—Si(Q 31 )(Q 32 )(Q 33 );

wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and C 6 -C 60 aryl group.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 18, 2019

From: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

Reel/Frame 051366/0480 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2015

From: DAS, RUPASREE RAGINI; LEE, KANGMUN; NOH, CHANGHO; BAE, HYEJIN; RAI, VIRENDRA KUMAR; KRAVCHUK, DMITRY

To: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.

Reel/Frame 036237/0162 →

Priority Claims (2)

KR 10-2014-0094157 · Jul 24, 2014 · national

KR 10-2015-0048325 · Apr 6, 2015 · national

Continuity (1)

Related Publication 20160028026A1 · Jan 28, 2016