IP Library › Granted Patent US 10,923,667

Granted Patent B2

US 10,923,667 · App. 15/915,131 · Granted Feb 16, 2021

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

Inventors: Sangho Park (Anyang-si, KR); Wataru Sotoyama (Yokohama, JP); Wook Kim (Suwon-si, KR); Eunsuk Kwon (Suwon-si, KR); Sangmo Kim (Hwaseong-si, KR); Jaejun Chang (Seoul, KR); Dmitry Kravchuk (Hwaseong-si, KR); Hyejin Bae (Suwon-si, KR); Yeonsook Chung (Seoul, KR); Youngmok Son (Hwaseong-si, KR); Namheon Lee (Suwon-si, KR); Jun Chwae (Seoul, KR); Sunghan Kim (Seongnam-si, KR)

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

H01L51/0085 C07F15/0033 C09K11/06 H01L51/0067 H01L51/0072 H01L51/50 C09K2211/1059 C09K2211/185 H01L51/001 H01L51/5012 H01L51/5072 H01L51/5088 H01L51/5092 H01L51/5096 H01L51/5206 H01L51/56 H01L2251/308 H01L2251/558

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Quick Facts

Patent No.: US 10,923,667
App. No.: 15/915,131
Granted: Feb 16, 2021
Kind: B2

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Abstract

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

Claims (135)

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,

M 1 is selected from a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, and a third-row transition metal of the Periodic Table of Elements,

n1 is 1, 2, or 3,

n2 is 0, 1, 2, 3, or 4, wherein, when n2 is two or more, two or more groups L 2 are identical to or different from each other,

X 1 and X 2 are each independently carbon or nitrogen,

CY 1 and CY 2 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

X 19 is N or C(R 19 ), and X 20 is N or C(R 20 ), provided that at least one of X 19 and X 20 is N,

L 2 in Formula 1 is selected form ligands represented by Formulae 3A to 3C and 3E to 3F:

R 1 , R 2 , R 11 to R 16 , R 19 , and R 20 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 1 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 aryloxy group, a substituted or unsubstituted C 1 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),

two or more neighboring groups selected from R 1 , R 2 , R 11 to R 13 , CY 1 , and CY 2 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 2 -C 30 heterocyclic group,

a1 and a2 are each independently an integer from 0 to 5,

at least one substituent of the substituted C 5 -C 30 carbocyclic group, the substituted C 2 -C 30 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 1 -C 60 aryl group, the substituted C 1 -C 60 aryloxy group, the substituted C 1 -C 60 arylthio group, the substituted C 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:

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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from 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 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 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), and —P(═O)(Q 18 )(Q 19 );

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 1 -C 60 aryl group, a C 1 -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 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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 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 1 -C 60 aryl group, a C 1 -C 60 aryloxy group, a C 1 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), and —P(═O)(Q 28 )(Q 29 ); and

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), and —P(═O)(Q 38 )(Q 39 ), and

Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently selected from 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 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 1 -C 60 aryl group, a C 1 -C 60 aryl group substituted with at least one selected from a C 1 -C 60 alkyl group and a C 1 -C 60 aryl group, a C 1 -C 60 aryloxy group, a C 1 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,

wherein, in Formulae 3A so 3C and 3E to 3F,

Y 11 is selected from O, N, N(Z 1 ), P(Z 1 )(Z 2 ), and As(Z 1 )(Z 2 ),

Y 12 is selected from O, N, N(Z 3 ), P(Z 3 )(Z 4 ), and As(Z 3 )(Z 4 ),

CY 11 is a C 2 -C 30 heterocyclic group,

T 11 is selected from a single bond, a double bond, *—C(Z 11 )(Z 12 )—*′, *—C(Z 11 )═C(Z 12 )—*′, *═C(Z 11 )—*′, *—C(Z 11 )=*′, *═C(Z 11 )—C(Z 12 )═C(Z 13 )—*′, *—C(Z 11 )═C(Z 12 )—C(Z 13 )=*′, *—N(Z 11 )—*′, and a substituted or unsubstituted C 5 -C 30 carbocylic group,

a11 is an integer from 1 to 10,

Y 13 to Y 14 are each independently carbon (C) or nitrogen (N), Y 13 and Y 14 are linked via a single bond or a double bond,

CY 12 and CY 13 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

A 1 is P or As,

Z 1 to Z 4 and Z 11 to Z 13 are each independently selected from 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 croup 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 subsumed 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 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),

Q 1 to Q 9 are each independently selected from 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 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 cycloalkyenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryl group substituted with at least one selected from a C 1 -C 60 alkyl group and 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 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroaralkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,

d1 and d2 are each independently an integer from 0 to 10, and

* and *′ each indicate a binding site to M 1 in Formula 1.

2. The organometallic compound of claim 1 , wherein

M 1 is Ir or Os, and the sum of n1 and n2 is 3 or 4; or

M 1 is Pt, and the sum of n1 and n2 is 2.

3. The organometallic compound of claim 1 , wherein

CY 1 and CY 2 are each independently selected from a cyclopentene group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, and a thiadiazole group.

4. The organometallic compound of claim 1 , wherein

X 19 is C(R 19 ), and X 20 is N; or

X 19 is N, and X 20 is C(R 20 ).

5. The organometallic compound of claim 1 , wherein

R 1 , R 2 , R 11 to R 16 , R 19 , and R 20 are each independently selected from:

hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , 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, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbomanyl group, a norbomenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ), and

Q 1 to Q 9 are each independently selected from:

—CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and -CD 2 CDH 2 ;

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and

6. The organometallic compound of claim 1 , wherein

R 1 , R 2 , R 11 to R 16 , R 19 , and R 20 are each independently selected from hydrogen, deuterium, —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, —CD 2 CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , groups represented by Formulae 9-1 to 9-24, groups represented by Formulae 10-1 to 10-62, and —Si(Q 3 )(Q 4 )(Q 5 ):

wherein * in Formulae 9-1 to 9-24 and 10-1 to 10-62 indicates a binding site to a neighboring atom.

7. The organometallic compound of claim 1 , wherein

i) X 19 is C(R 19 ), X 20 is N, and at least one of R 1 , R 2 , R 11 to R 16 , and R 19 is a deuterium-containing substituent;

ii) X 19 is N, X 20 is C(R 20 ), and at least one of R 1 , R 2 , R 11 to R 16 , and R 20 is a deuterium-containing substituent; or

iii) X 19 and X 20 are each N, and at least one of R 1 , R 2 , and R 11 to R 16 is a deuterium-containing substituent, and

the deuterium-containing substituent is selected from:

deuterium; and

a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a phenyl group, each substituted with at least one deuterium.

8. The organometallic compound of claim 7 , wherein

the deuterium-containing substituent is selected from:

deuterium; and

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 deuterium.

9. The organometallic compound of claim 1 , wherein

i) X 19 is C(R 19 ), X 20 is N, and at least one of R 12 , R 14 , and R 19 is a deuterium-containing substituent;

ii) X 19 is N, X 20 is C(R 20 ), and at least one of R 12 , R 14 , and R 20 is a deuterium-containing substituent; or

iii) X 19 and X 20 are each N, and at least one of R 12 and R 14 is a deuterium-containing substituent, and

the deuterium-containing substituent is selected from:

deuterium; and

10. The organometallic compound of claim 1 , wherein

the organometallic compound is represented by one of Formulae 1-1 to 1-3:

wherein, in Formulae 1-1 to 1-3, M 1 , n1, L 2 , n2, R 11 to R 16 , R 19 , and R 20 are each independently the same as described in claim 1 , R 1a to R 1e are each independently the same as described in connection with R 1 in claim 1 , and R 2a to R 2e are each independently the same as described in connection with R 2 in claim 1 .

11. The organometallic compound of claim 1 , wherein

the organometallic compound is represented by one of Formulae 1(1) to 1(3):

wherein, in Formulae 1(1) to 1(3), M 1 , n1, L 2 , n2, R 12 , R 14 , R 19 , and R 20 are each independently the same as described in claim 1 , R 1a and R 1e are each independently the same as described in connection with R 1 in claim 1 , and R 2a and R 2e are each independently the same as described in connection with R 2 in claim 1 .

12. The organometallic compound of claim 1 , wherein

the organometallic compound is one of Compounds 1 to 10:

13. The organometallic compound of claim 1 , wherein

the organometallic compound has a natural population analysis (NPA) charge value of about 0.6 or less, and

the NPA charge value is evaluated by a density functional theory (DFT) method using a Gaussian program that is structurally optimized at a level of B3LYP/6-31G(d,p).

14. The organometallic compound of claim 1 , wherein

the organometallic compound has an NPA charge value of about 0.4 to about 0.55, and

the NPA charge value is evaluated by a DFT method using a Gaussian program that is structurally optimized at a level of B3LYP/6-31G(d,p).

15. 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,

wherein the organic layer comprises at least one of the organometallic compound of claim 1 .

16. The organic light-emitting device of claim 15 , wherein

the emission layer comprises the organometallic compound or the composition.

17. The organic light-emitting device of claim 16 , wherein

the emission layer further comprises a host.

18. The organic light-emitting device of claim 17 , wherein

the host is selected from the following compounds:

19. A composition containing an organometallic compound, the composition comprising:

a first organometallic compound represented by Formula 1 and comprising at least one deuterium; and

a second organometallic compound represented by Formula 2:

wherein, in Formulae 1 and 2,

M 1 and M 11 are each independently selected from a first-row transition metal of the Periodic Table of Elements, a second-row transition metal of the Periodic Table of Elements, and a third-row transition metal of the Periodic Table of Elements,

n1 and n11 are each independently 1, 2, or 3,

L 2 in Formula 1 is selected from ligands represented by Formulae 3A to 3C and 3E to 3F:

L 12 is a monodentate ligand or a bidentate ligand,

n2 and n12 are each independently 0, 1, 2, 3, or 4, wherein, when n2 is two or more, two or more L 2 are identical to or different from each other, and when n12 is two or more, two or more groups Li 2 are identical to or different from each other,

X 1 to X 4 are each independently carbon or nitrogen,

CY 1 to CY 4 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

X 19 is N or C(R 19 ), and X 20 is N or C(R 20 ), provided that at least one of X 19 and X 20 is N,

X 29 is N or C(R 29 ), and X 30 is N or C(R 30 ), provided that at least one of X 29 and X 30 is N,

a1 and a2 are each independently an integer from 0 to 5,

i) X 19 is C(R 19 ), X 20 is N, and at least one of R 1 , R 2 , R 11 to R 16 , and R 19 is a deuterium-containing substituent; ii) X 19 is N, X 20 is C(R 20 ), and at least one of R 1 , R 2 , R 11 to R 16 , and R 20 is a deuterium-containing substituent; or iii) X 19 and X 20 are each N, and at least one of R 1 , R 2 , and R 11 to R 16 is a deuterium-containing substituent,

R 3 , R 4 , R 21 to R 26 , R 29 , and R 30 are each independently selected from hydrogen, —F, —Cl, —Br, —I, —SF 5 , 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 1 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 aryloxy group, a substituted or unsubstituted C 1 -C 60 arylthio group, a substituted or unsubstituted C 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),

two or more neighboring groups selected from R 3 , R 4 , R 21 to R 23 , CY 3 , and CY 4 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 2 -C 30 heterocyclic group,

a3 and a4 are each independently an integer from 0 to 5,

R 3 , R 4 , R 21 to R 26 , R 29 , and R 30 are each a deuterium-free substituent;

wherein, in Formulae 3A so 3C and 3E to 3F,

Y 11 is selected from O, N, N(Z 1 ), P(Z 1 )(Z 2 ), and As(Z 1 )(Z 2 ),

Y 12 is selected from O, N, N(Z 3 ), P(Z 3 )(Z 4 ), and As(Z 3 )(Z 4 ),

CY 11 is a C 2 -C 30 heterocyclic group,

a11 is an integer from 1 to 10,

Y 13 to Y 14 are each independently carbon (C) or nitrogen (N), Y 13 and Y 14 are linked via a single bond or a double bond,

CY 12 and CY 13 are each independently a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group,

A 1 is P or As,

d1 and d2 are each independently an integer from 0 to 10, and

* and *′ each indicate a binding site to M 1 in Formula 1.

20. The composition of claim 9 , wherein

a deuteration rate represented by Equation 2 is about 50% or more:

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

wherein, in Equation 2,

n H2 represents the sum of a total number of hydrogens included in deuterium-containing substituents in the first organometallic compound and a total number of hydrogens included in a deuterium-free substituent of the second organometallic compound corresponding to the deuterium-containing substituent in the first organometallic compound, and

n D2 represents a total number of deuterium atoms included in the deuterium-containing substituents in the first organometallic compound.

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 Mar 15, 2018

From: PARK, SANGHO; SOTOYAMA, WATARU; KIM, WOOK; KWON, EUNSUK; KIM, SANGMO; CHANG, JAEJUN; KRAVCHUK, DMITRY; BAE, HYEJIN; CHUNG, YEONSOOK; SON, YOUNGMOK; LEE, NAMHEON; CHWAE, JUN; KIM, SUNGHAN

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

Reel/Frame 045227/0346 →

Priority Claims (2)

KR 10-2017-0029608 · Mar 8, 2017 · national

KR 10-2018-0026443 · Mar 6, 2018 · national

Continuity (1)

Related Publication 20180261780A1 · Sep 13, 2018