IP Library › Granted Patent US 10,651,402
Granted Patent B2
US 10,651,402 · App. 15/270,703 · Granted May 12, 2020

Organometallic compound and organic light-emitting device including the same

Inventors: Kum Hee Lee (Suwon-si, KR); Kyuyoung Hwang (Anyang-si, KR); Yoonhyun Kwak (Seoul, KR); Ohyun Kwon (Yongin-si, KR); Aram Jeon (Suwon-si, KR); Hyeonho Choi (Seoul, KR); Byoungki Choi (Hwaseong-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H01L51/0085C07F15/0033C09K11/06C09K2211/1029C09K2211/185H01L51/5016H01L51/5206H01L51/5221
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Quick Facts
Patent No.
US 10,651,402
App. No.
15/270,703
Granted
May 12, 2020
Kind
B2
Abstract

An organometallic compound represented by Formula 1: wherein, in Formula 1, b18, A 11 , L 11 , M, m, R 18 , and X 11 to X 17 are the same as described in the specification.

Claims (83)

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,

M is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal;

A 11 is selected from a C 3 -C 14 heterocyclic group condensed with a 6-membered ring group and a C 3 -C 14 heterocyclic group condensed with a 5-membered ring group,

the C 3 -C 14 heterocyclic group is selected from a pyrrole group, a pyrazole group, an imidazole group, a thiazole group, an isothiazole group, an oxazole group, an iso-oxazole group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a thiazine group, an oxazine group, a quinoline group, an isoquinoline group, a cinnoline group, a quinazoline group, a quinoxaline group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 1,8-naphthyridine group, a phthalazine group, 2,6-naphthyridine group, and 2,7-naphthyridine group, the 6-membered ring group is selected from a benzene group, a cyclohexane group, a cyclohexene group, a pyridine group, a piperidine group, a pyrazine group, a hexahydropyrimidine group, a tetrahydropyrazine group, and a piperazine group, and the 5-membered ring group is selected from a cyclopentene group, a cyclopentadiene group, a dihydropyrrole group, a pyrrole group, an imidazole group, and a pyrrolidine group;

X 11 is N, X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is N, X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is CR 12 , X 13 is N, X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is N, X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is N, X 16 is CR 16 , and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is N, and X 17 is CR 17 ;

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is N; or

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ;

R 11 to R 18 are each independently selected from a hydrogen, 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 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, —C(═O)(Q 1 ), —N(Q 1 )(Q 2 ), and —Si(Q 1 )(Q 2 )(Q 3 ), wherein at least two adjacent groups of R 11 to R 17 are optionally linked to each other to form a saturated or unsaturated ring;

Q 1 to Q 3 are each independently selected from a hydrogen, deuterium, a substituted or unsubstituted C 1 -C 10 alkyl group, and a substituted or unsubstituted C 6 -C 60 aryl group;

b18 is selected from 1, 2, 3, 4, 5, 6, 7, and 8;

n is 1, 2, 3, and 4;

L 11 is selected from a monodentate ligand or a bidentate ligand selected from the group consisting of an oxalate, an acetylacetonate, a picolinic acid, a 2-(2-hydroxyphenyl)-pyridine, 2-phenylpyridine, a 1,2-bis(diphenylphosphino)ethane, a 1,1-bis(diphenylphosphino)methane, a glycinate, an ethylenediamine, a 2,2′-bipyridine, a 1,10-phenanthroline and ligands represented by Formulae 2-1 to 2-3;

wherein, in Formulae 2-1 to 2-3,

A 21 is selected from a C 5 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group;

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

Y 21 is selected from a single bond, a double bond, a substituted or unsubstituted C 1 -C 5 alkylene group, a substituted or unsubstituted C 2 -C 5 alkenylene group, and a substituted or unsubstituted C 6 -C 10 arylene group;

Z 21 and Z 22 are each independently selected from N, O, N(R 25 ), P(R 25 )(R 26 ), and As(R 25 )(R 26 );

R 21 to R 26 are each independently selected from a hydrogen, 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 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 of 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 phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group;

b21 is selected from 1, 2, and 3; and

* and *′ are each independently a binding site with an adjacent atom; and

m is selected from 0, 1, 2, 3, 4, 5, and 6.

2. The organometallic compound of claim 1 , wherein M is selected from iridium (Ir), platinum (Pt), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

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

4. The organometallic compound of claim 1 , wherein A 11 is selected from a quinoline group, an isoquinoline group, a cinnoline group, a quinazoline group, a quinoxaline group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 1,8-naphthyridine group, a phthalazine group, 2,6-naphthyridine group, 2,7-naphthyridine group, an indole group, an isoindole group, a benzimidazole group, a benzothiazole group, a benzisothiazole group, a benzoxazole group, a benzisoxazole group, a benzothiazine group, a benzoxazine group, a benzoquinoline group, a benzisoquinoline group, a phenanthroline group, and a phenanthridine group.

5. The organometallic compound of claim 1 , wherein A 11 is selected from a quinoline group, an isoquinoline group, a quinazoline group, a quinoxaline group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 1,8-naphthyridine group, a phthalazine group, 2,6-naphthyridine group, 2,7-naphthyridine group, an indole group, an isoindole group, a benzimidazole group, a benzothiazole group, a benzisothiazole group, a benzoxazole group, a benzisoxazole group, a benzothiazine group, and a benzoxazine group.

6. The organometallic compound of claim 1 , wherein A 11 is selected from a quinoline group, an isoquinoline group, and a benzimidazole group.

7. The organometallic compound of claim 1 , wherein X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is CR 17 ; or

X 11 is CR 11 , X 12 is CR 12 , X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , and X 17 is N.

8. The organometallic compound of claim 1 , wherein R 11 to R 18 are each independently selected from

a hydrogen, 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 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 of 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 phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, and

—C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —N(Q 1 )(Q 2 ), wherein Q 1 to Q 3 are each independently selected from substituted or unsubstituted C 1 -C 20 alkyl groups.

9. The organometallic compound of claim 1 , wherein R 11 to R 18 are each independently selected from

hydrogen, 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, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, and a tert-butoxy group,

a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, and a naphthyl group;

a phenyl group and a naphthyl group;

a phenyl group and a naphthyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a tert-butoxy group, a phenyl group, and a naphthyl group; and

—Si(Q 1 )(Q 2 )(Q 3 ), wherein Q 1 to Q 3 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, and a tert-butyl group.

10. The organometallic compound of claim 1 , wherein n is selected from 1, 2, and 3.

11. The organometallic compound of claim 1 , wherein L 11 is a ligand represented by one of Formulae 2-1 to 2-5:

wherein, in Formulae 2-1 to 2-5,

A 21 is selected from a C 5 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group;

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

Y 21 is selected from a single bond, a double bond, a substituted or unsubstituted C 1 -C 5 alkylene group, a substituted or unsubstituted C 2 -C 5 alkenylene group, and a substituted or unsubstituted C 6 -C 10 arylene group;

Z 21 and Z 22 are each independently selected from N, O, N(R 25 ), P(R 25 )(R 26 ), and As(R 25 )(R 26 );

Z 23 is selected from phosphorus (P) and arsenic (As);

R 21 to R 26 are each independently selected from a hydrogen, 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 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 of 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 phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group, each substituted with at least one of deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , 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 C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridinyl group;

b21 is selected from 1, 2, and 3; and

* and *′ are each independently a binding site with an adjacent atom.

12. The organometallic compound of claim 1 , wherein L 11 is a ligand represented by one of Formulae 3-1 to 3-6:

wherein, in Formulae 3-1 to 3-6,

Ph is a phenyl group; and

* and *′ are binding sites with an adjacent atom.

13. The organometallic compound of claim 1 , wherein m is selected from 0, 1, 2, 3, and 4.

14. The organometallic compound of claim 1 , wherein the organometallic compound of Formula 1 is represented by one of Formulae 1-1 to 1-4:

wherein, in Formulae 1-1 to 1-4,

M, X 7 to X 17 , R 18 , b18, n, L 11 , and m are the same as those in Formula 1; and

R 19 is the same as R 18 in Formula 1.

15. The organometallic compound of claim 1 , wherein the organometallic compound of Formula 1 is represented by one of Formulae 1-11 to 1-18:

wherein, in Formulae 1-11 to 1-18,

M, R 11 to R 18 , b18, n, L 11 , and m are the same as those in Formula 1; and

R 19 is the same as R 18 in Formula 1.

16. The organometallic compound of claim 1 , wherein the organometallic compound of Formula 1 is selected from Compounds 1 to 30:

17. 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 represented by Formula 1 of claim 1 .

18. The organic light-emitting device of claim 17 , wherein the emission layer comprises the at least one organometallic compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2016
From: LEE, KUM HEE; HWANG, KYUYOUNG; KWAK, YOONHYUN; KWON, OHYUN; JEON, ARAM; CHOI, HYEONHO; CHOI, BYOUNGKI
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 040510/0560 →
Priority Claims (1)
KR 10-2015-0138594 · Oct 1, 2015 · national
Continuity (1)
Related Publication 20170098788A1 · Apr 6, 2017