IP Library › Granted Patent US 10,326,086

Granted Patent B2

US 10,326,086 · App. 15/013,404 · Granted Jun 18, 2019

Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound or composition

Inventors: Wook Kim (Hwaseong-si, KR); Changho Noh (Suwon-si, KR); Rupasree Ragini Das (Suwon-si, KR); Youngseok Park (Seoul, KR); Hyejin Bae (Suwon-si, KR); Miyoung Chae (Suwon-si, KR); Dmitry Kravchuk (Hwaseong-si, KR)

Assignee: SAMSUNG ELECTRONICS CO., LTD.

H01L51/0085 C07F15/0033 C09K11/025 C09K11/06 H01L51/0067 B32B2457/206 C09K2211/1007 C09K2211/1044 C09K2211/1088 C09K2211/185 H01L51/006 H01L51/0072 H01L51/0094 H01L51/5004 H01L51/5012 H01L51/5016 H01L2251/552

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Quick Facts

Patent No.: US 10,326,086
App. No.: 15/013,404
Granted: Jun 18, 2019
Kind: B2

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Abstract

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

Claims (138)

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,

M 11 is a first-row transition metal, a second-row transition metal, or a third-row transition metal;

R 11 to R 18 are each independently a hydrogen, a deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a carbonyl 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 30 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

optionally, adjacent two of R 11 to R 15 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;

at least one of R 11 to R 15 is selected from the group consisting of a substituted or unsubstituted C 3 -C 30 branched alkyl 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

R 19 and R 20 are each independently a hydrogen, a deuterium, a C 1 -C 30 alkyl group, or a deuterium-substituted C 1 -C 30 alkyl group;

at least one of R 11 to R 20 is a deuterium-containing substituent;

n11 is 1, 2, or 3;

L 11 is a monodentate ligand or a bidentate ligand selected from the group consisting of an oxalate, an acetylacetonate, a picolinic acid, a 1,2-bis(diphenylphosphino)ethane, a 1,1-bis(diphenylphosphino)methane, a glycinate, an ethylenediamine, and ligands represented by Formulae 4-1 to 4-4:

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

X 41 iS CR 41 or a nitrogen atom (N);

X 42 is CR 42 or N;

X 45 iS O, S, or N(R 45 );

Y 41 and Y 42 are each independently C or N;

Z 21 and Z 22 are each independently N, O, N(R 48 ), P(R 48 )(R 49 ), or As(R 48 )(R 49 );

Z 23 is CO or CH 2 ;

A 41 to A 43 are each independently a C 3 -C 10 cycloalkane, a C 1 -C 10 heterocycloalkane, a C 3 -C 10 cycloalkene, a C 1 -C 10 heterocycloalkene, a C 6 -C 10 arene, a C 1 -C 10 heteroarene, a non-aromatic condensed polycycle, or a non-aromatic condensed heteropolycycle, wherein a bond between A 41 and A 42 in Formula 4-1 is a carbon-carbon bond;

R 41 to R 49 are each independently a hydrogen, a deuterium, —F, —CI, —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 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or —Si(Q 41 )(Q 42 )(Q 43 );

optionally, adjacent two of R 41 to R 44 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;

optionally, R 46 and R 47 are linked to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring;

b43 and b44 are each independently an integer of 1 to 5;

Q 41 to Q 43 are each independently a hydrogen, a deuterium, —F, —CI, —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, 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; and

* and *′ are each independently a binding site to M 11 in Formula 1; and

m11 is 0, 1, 2, 3, or 4.

2. The organometallic compound of claim 1 , wherein M 11 is Ir or Pt.

3. The organometallic compound of claim 1 , wherein R 11 to R 18 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group, wherein optionally, adjacent two of R 11 to R 15 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,

X 11 is O, S, or N(R 105 );

R 101 to R 105 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group; and

* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

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

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, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, —Si(Q 1 )(Q 2 )(Q 3 ),

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a cyano group,

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one of 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, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, or

—Si(Q 4 )(Q 5 )(Q 6 ),

wherein Q 1 to Q 3 are each independently a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, or a tert-pentyl group; and

Q 4 to Q 6 are each independently

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, or a tert-pentyl group, each substituted with at least one selected from the group consisting of a deuterium, —F, —Cl, —Br, —I, and a cyano group,

wherein at least one of Q 4 to Q 6 is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, and a cyano group; and

optionally, adjacent two of R 11 to R 15 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,

X 11 is O, S, or N(R 105 );

R 101 to R 105 are each independently 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, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group; and

* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

5. The organometallic compound of claim 1 , wherein at least one of R 11 to R 15 is selected from the group consisting of a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group, and

optionally, adjacent two of R 11 to R 15 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,

X 11 is O, S, or N(R 105 );

R 101 to R 105 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a carbonyl 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 10 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

6. The organometallic compound of claim 1 , wherein at least one of R 11 to R 15 is selected from the group consisting of

an iso-propyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, —Si(Q 1 )(Q 2 )(Q 3 ),

an iso-propyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a cyano group,

—Si(Q 4 )(Q 5 )(Q 6 ),

Q 4 to Q 6 are each independently

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, each substituted with at least one selected from the group consisting of a deuterium, —F, —Cl, —Br, —I, and a cyano group;

at least one of Q 4 to Q 6 is selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I and a cyano group; and

optionally, adjacent two of R 11 to R 15 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,

X 11 is O, S, or N(R 105 );

* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

7. The organometallic compound of claim 1 , wherein at least one of R 11 to R 15 is selected from the group consisting of an iso-propyl group, an iso-butyl group, a tert-butyl group, a neo-pentyl group, a phenyl group, a biphenyl group, —Si(CH 3 ) 3 ,

an iso-propyl group, an iso-butyl group, a tert-butyl group, a neo-pentyl group, each substituted with a deuterium,

a phenyl group, a biphenyl group, each substituted with a deuterium, and

Si(CD 3 ) 3 , and

optionally, R 12 and R 13 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,

X 11 is O, S, or N(R 105 );

* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

8. The organometallic compound of claim 1 , wherein R 19 is a deuterium and R 20 is a hydrogen; R 19 is a hydrogen and R 20 is a deuterium; or R 19 and R 20 are both deuterium.

9. The organometallic compound of claim 1 , wherein the deuterium-containing substituent is

a deuterium, or

a C 1 -C 30 alkyl group, a C 3 -C 30 branched alkyl group, a C 2 -C 30 alkenyl group, a C 2 -C 30 alkynyl group, a C 1 -C 30 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 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a C 7 -C 30 arylalkyl group, a C 1 -C 30 heteroaryl group, a C 2 -C 30 heteroaryloxy group, a C 2 -C 30 heteroarylthio group, a C 3 -C 30 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a C 1 -C 30 alkylsilyl group, each substituted with a deuterium.

10. The organometallic compound of claim 1 , wherein the deuterium-containing substituent is

a deuterium,

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, a tert-pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, each substituted with a deuterium, or

—Si(Q 4 )(Q 5 )(Q 6 ),

wherein Q 4 to Q 6 are each independently

11. The organometallic compound of claim 1 , wherein the deuterium-containing substituent is

-D, —CH 2 D, —CHD 2 , —CD 3 , —CH 2 CH 2 D, —CH 2 CHD 2 , —CH 2 CD 3 , —CHDCH 3 , —CHDCH 2 D, —CHDCHD 2 , —CHDCD 3 , —CD 2 CH 3 , —CD 2 CH 2 D, —CD 2 CHD 2 , —CD 2 CD 3 , —CH 2 CH 2 CH 2 D, —CH 2 CH 2 CHD 2 , —CH 2 CH 2 CD 3 , —CH 2 CHDCH 3 , —CH 2 CHDCH 2 D, —CH 2 CHDCHD 2 , —CH 2 CHDCD 3 , —CH 2 CD 2 CH 3 , —CH 2 CD 2 CH 2 D, —CH 2 CD 2 CHD 2 , —CH 2 CD 2 CD 3 , —CHDCH 2 CH 2 D, —CHDCH 2 CHD 2 , —CHDCH 2 CD 3 , —CHDCHDCH 3 , —CHDCHDCH 2 D, —CHDCHDCHD 2 , —CHDCHDCD 3 , —CHDCD 2 CH 3 , —CHDCD 2 CH 2 D, —CHDCD 2 CHD 2 , —CHDCD 2 CD 3 , —CD 2 CH 2 CH 2 D, —CD 2 CH 2 CHD 2 , —CD 2 CH 2 CD 3 , —CD 2 CHDCH 3 , —CD 2 CHDCH 2 D, —CD 2 CHDCHD 2 , —CD 2 CHDCD 3 , —CD 2 CD 2 CH 3 , —CD 2 CD 2 CH 2 D, —CD 2 CD 2 CHD 2 , —CD 2 CD 2 CD 3 , —CH(CH 3 )(CH 2 D), —CH(CH 3 )(CHD 2 ), —CH(CH 2 D) 2 , —CH(CH 3 )(CD 3 ), —CH(CHD)(CHD 2 ), —CH(CH 2 D)(CD 3 ), —CH(CHD 2 ) 2 , —CH(CHD 2 )(CD 3 ), —CH(CD 3 ) 2 , —CD(CH 3 ) 2 , —CD(CH 3 )(CH 2 D), —CD(CH 3 )(CHD 2 ), —CD(CH 2 D)(CH 2 D), —CD(CH 3 )(CD 3 ), —CD(CH 2 D)(CHD 2 ), —CD(CH 2 D)(CD 3 ), —CD(CHD 2 ) 2 , —CD(CHD 2 )(CD 3 ), —CD(CD 3 ) 2 , —CD 2 CD(CD 3 ) 2 , —C(CD 3 ) 3 , —CD 2 C(CD 3 ) 3 , or a group represented by any one of Formulae 3-1 to 3-5:

wherein, in Formulae 3-1 to 3-5, * is a binding site to an adjacent atom.

12. The organometallic compound of claim 1 , wherein L 11 is a bidentate ligand.

13. The organometallic compound of claim 1 , wherein M 11 is iridium (Ir); and n11 is 2 or 3.

14. The organometallic compound of claim 1 , wherein M 11 is platinum (Pt); and n11 is 1 or 2.

15. The organometallic compound of claim 1 , wherein the organometallic compound of Formula 1 is a compound represented by one of Formulae 1-11 to 1-22:

wherein, in Formulae 1-11 to 1-22,

M 11 , R 11 to R 20 , n 11 , L 11 , and m11 are defined the same as those in Formula 1;

X 11 is O, S, or N(R 105 );

R 11x , R 12x , R 13x , R 14x , R 15x , R 16x , R 17x , R 18x , R 19x , R 20x , R 101x , R 102x , R 103x , and R 104x are each independently a deuterium-containing substituent.

16. An organometallic compound-containing composition comprising a first organometallic compound represented by Formula 1 and a second organometallic compound represented by Formula 2:

wherein, in Formulae 1 and 2,

R 11 to R 18 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a carbonyl 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 30 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

optionally, adjacent two of R 11 to R 15 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;

at least one of R 11 to R 15 is a substituted or unsubstituted C 3 -C 30 branched alkyl 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

R 19 and R 20 are each independently a hydrogen, a deuterium, a C 1 -C 30 alkyl group, or a deuterium-substituted C 1 -C 30 alkyl group;

at least one of R 11 to R 20 is a deuterium-containing substituent;

R 21 to R 28 are each independently a hydrogen, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a carbonyl 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 30 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

optionally, adjacent two of R 21 to R 25 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;

at least one of R 21 to R 25 is selected from the group consisting of a substituted or unsubstituted C 3 -C 30 branched alkyl 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group;

R 29 and R 30 are each independently a hydrogen or a C 1 -C 30 alkyl group;

R 21 to R 30 are each a substituent containing no deuterium;

M 11 and M 21 are each independently a first-row transition metal, a second-row transition metal, or a third-row transition metal;

n11 and n21 are each independently 1, 2, or 3;

L 11 and L 21 are each independently a monodentate ligand or a bidentate ligand; and

m11 and m21 are each independently 0, 1, 2, 3, or 4.

17. The organometallic compound-containing composition of claim 16 , wherein the organometallic compound-containing composition has a deuteration rate of 50% or more, wherein the deuteration rate is represented by Equation 2:

Deuteration rate (%)= n D2 /( n H2 +n D2 )×100 Equation 2

wherein, in Equation 2,

n H2 represents a sum of a total number of hydrogens in the deuterium-containing substituents and a total number of hydrogens in substituents that are equivalent to the deuterium-containing substituents; and

n D2 represents a total number of deuterium atoms in the deuterium-containing substituents.

18. 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 the organometallic compound of claim 1 .

19. The organic light-emitting device of claim 18 , wherein the emission layer comprises the organometallic compound or the organometallic compound-containing composition,

wherein the emission layer further comprises a host, and

wherein the organometallic compound in the emission layer is a dopant.

20. 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 the organometallic compound-containing composition of claim 16 .

21. The organic light-emitting device of claim 20 , wherein the emission layer comprises the organometallic compound-containing composition,

wherein the emission layer further comprises a host, and

wherein each of the first organometallic compound and the second organometallic compound in the emission layer is a dopant.

22. The organometallic compound of claim 1 , wherein m11 is 0.

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 Feb 2, 2016

From: KIM, WOOK; NOH, CHANGHO; DAS, RUPASREE RAGINI; PARK, YOUNGSEOK; BAE, HYEJIN; CHAE, MIYOUNG; KRAVCHUK, DMITRY

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

Reel/Frame 037647/0212 →

Priority Claims (2)

KR 10-2015-0018868 · Feb 6, 2015 · national

KR 10-2016-0011879 · Jan 29, 2016 · national

Continuity (1)

Related Publication 20160233441A1 · Aug 11, 2016