IP Library › Granted Patent US 12,404,290
Granted Patent B2
US 12,404,290 · App. 18/406,353 · Granted Sep 2, 2025

Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Inventors: Jeoungin Yi (Seoul, KR); Seungyeon Kwak (Suwon-si, KR); Juhyun Kim (Seoul, KR); Sangho Park (Anyang-si, KR); Sunyoung Lee (Seoul, KR); Jiyoun Lee (Anyang-si, KR); Yoonhyun Kwak (Seoul, KR); Hyun Koo (Seongnam-si, KR); Sunghun Lee (Hwaseong-si, KR); Hyeonho Choi (Seoul, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07F15/0033C09K11/06H10K85/342C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/185H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18
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Quick Facts
Patent No.
US 12,404,290
App. No.
18/406,353
Granted
Sep 2, 2025
Kind
B2
Abstract

Provided is an organometallic compound represented by Formula 1, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device. M(L 1 ) n1 (L 2 ) n2   <Formula 1> M, L 1 , L 2 , n1, and n2 in Formula 1 are the same as described in the present specification.

Claims (120)

1. An organometallic compound which is represented by Formula 1 and capable of emitting phosphorescent light:

M(L 1 ) n1 (L 2 ) n2   <Formula 1>

wherein, in Formula 1,

M is Ir, Os, or Pt,

L 1 is a ligand represented by Formula 2A or 2B,

n1 is 1, 2, or 3, wherein, when n1 is 2 or more, two or more of L(s) are identical to or different from each other,

L 2 is a ligand represented by Formula 3D,

n2 is 1, or 2, wherein, when n2 is 2, two of L 2 (s) are identical to or different from each other, and

L 1 and L 2 are different from each other,

wherein, when M is Ir or Os, the sum of n1 and n2 is 3 or 4, and when M is Pt, the sum of n1 and n2 is 2,

X 3 is Se, B(R 2 ), N(R 2 ), P(R 2 ), C(R 2 )(R 3 ), Si(R 2 )(R 3 ), Ge(R 2 )(R 3 ), N, C(R 2 ), or Si(R 2 ),

ring CY 1 and ring CY 21 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

ring CY 2 is a 5-membered ring,

wherein, in Formulae 3D,

T 21 is a single bond, a double bond, O, S, C(Z 11 )(Z 12 ), Si(Z 11 )(Z 12 ), or N(Z 11 ),

ring CY 11 and ring CY 12 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

Z 1 and Z 2 are the same as described in R 21 ,

d1 and d2 are each independently an integer from 0 to 20, and

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

provided that:

(I) when L 1 is a ligand represented by Formula 2A, X 2 , X 4 , and X 5 are each C, X 21 is C, CY 1 is a benzene group, CY 21 is a benzene group or a pyridine group, and X 3 is N(R 2 ), then (i) n1 is 2 or 3, or (ii) R 2 is a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group, or (iii) any combination thereof,

(II) when L 1 is a ligand represented by Formula 2A, X 2 , X 4 , and X 5 are each C, X 21 is C, CY 1 is a benzene group, CY 21 is a benzene group or a pyridine group, X 3 is N(R 2 ), n1 is 1, n2 is 2, Y 11 is N, and Y 12 is C, then (i) d1 is 1 and Z 1 is not hydrogen or carboxylic group, (ii) d1 is 2 or more and Z 1 are each independently not hydrogen or amino group, (iii) d2 is 1 and Z 2 is not hydrogen or methyl group, (iv) d2 is 2 or more and Z 2 are each independently not hydrogen or halogen, or (v) any combination thereof,

R a , R b , R 1 to R 3 , and R 21 are each independently 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 1 -C 60 alkylthio 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, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),

a1 and a21 are each independently an integer from 0 to 20,

two or more of a plurality of R 1 (s) are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of a plurality of R 21 (s) are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of R a , R b , R 1 to R 3 , and R 21 are optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

R 10a is the same as described in connection with R 21 ,

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

at least one substituent of each of 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 1 -C 60 alkylthio 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 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

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, or any combination 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, or any combination thereof, each substituted with at least one 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 1 -C 60 heteroaryl 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 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof, each unsubstituted or substituted with at least one 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 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, 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 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or any combination thereof;

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), —P(Q 38 )(Q 39 ), or any combination thereof; or

any combination thereof,

wherein Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 are each independently: 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 which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; 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 which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a C 6 -C 60 aryloxy group; a C 6 -C 60 arylthio group; a C 1 -C 60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein a bond between X 1 of Formulae 2A and 2B and M of Formula 1 is a coordination bond, and a bond between Y 1 of Formulae 2A and 2B and M of Formula 1 is a covalent bond.

3. The organometallic compound of claim 1 , wherein ring CY 1 and ring CY 21 are each independently a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

4. The organometallic compound of claim 1 , wherein R a , R b , R 1 to R 3 , and R 21 are each independently:

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, —SF 5 , C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, or a C 1 -C 20 alkylthio group;

a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, or a C 1 -C 20 alkylthio group, each substituted with 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 10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C 1 -C 20 alkyl)cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cycloctyl group, a (C 1 -C 20 alkyl) adamantanyl group, a (C 1 -C 20 alkyl) norbornanyl group, a (C 1 -C 20 alkyl) norbornenyl group, a (C 1 -C 20 alkyl)cyclopentenyl group, a (C 1 -C 20 alkyl)cyclohexenyl group, a (C 1 -C 20 alkyl)cycloheptenyl group, a (C 1 -C 20 alkyl) bicyclo[1.1.1]pentyl group, a (C 1 -C 20 alkyl) bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl 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 benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl 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, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a (C 1 -C 20 alkyl)cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cycloctyl group, a (C 1 -C 20 alkyl) adamantanyl group, a (C 1 -C 20 alkyl) norbornanyl group, a (C 1 -C 20 alkyl) norbornenyl group, a (C 1 -C 20 alkyl)cyclopentenyl group, a (C 1 -C 20 alkyl)cyclohexenyl group, a (C 1 -C 20 alkyl)cycloheptenyl group, a (C 1 -C 20 alkyl) bicyclo[1.1.1]pentyl group, a (C 1 -C 20 alkyl) bicyclo[2.1.1]hexyl group, a (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a terphenyl 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 benzoisothiazolyl group, a benzoxazolyl group, an benzoisoxazolyl 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, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof; or

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

wherein Q 1 to Q 9 are each independently:

—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, or -CD 2 CDH 2 ; or

an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, a phenyl group, a biphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C 1 -C 10 alkyl group, a phenyl group, or any combination thereof.

5. The organometallic compound of claim 1 , wherein a group represented by

of Formula 2A is represented by one of Formulae 2A-1 to 2A-3,

a group represented by

in Formula 2B is represented by one of Formulae 2B-1 to 2B-3:

wherein, in Formulae 2A-1 to 2A-3 and 2B-1 to 2B-3, X 1 is N, X 2 is C, ring CY 1 , R 1 , and a1 are the same as in claim 1 , *′ is a binding site to M of Formula 1, and *″ is a binding site to ring CY 21 in Formulae 2A and 2B,

in Formulae 2A-1 and 2B-1, X 3 is Se, B(R 2 ), N(R 2 ), P(R 2 ), C(R 2 )(R 3 ), Si(R 2 )(R 3 ), or Ge(R 2 )(R 3 ), and X 4 and X 5 are each C,

in Formulae 2A-2 and 2B-2, X 3 is N, C(R 2 ), or Si(R 2 ), X 4 is C, and X 5 is C or N, and

in Formulae 2A-3 and 2B-3, X 3 is N, C(R 2 ) or Si(R 2 ), X 4 is C or N, and X 5 is C.

6. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2A is represented by one of Formulae 2A (1) to 2A(7),

a group represented by

in Formula 2B is represented by one of Formulae 2B (1) to 2B (7):

wherein, in Formulae 2A (1) to 2A (7) and 2B (1) to 2B (7),

X 1 is N,

*′ indicates a binding site to M of Formula 1,

*″ is a binding site to ring CY 21 in Formulae 2A and 2B,

X 3 is Se, B(R 2 ), N(R 2 ), P(R 2 ), C(R 2 )(R 3 ), Si(R 2 )(R 3 ), or Ge(R 2 )(R 3 ), and

R 11 to R 14 are the same as described in R 1 in claim 1 , and R 2 and R 3 are the same as described in claim 1 .

7. The organometallic compound of claim 1 , wherein a group represented by

in Formulae 2A and 2B is a group represented by one of Formulae CY21-1 to CY21-25:

wherein, in Formulae CY21-1 to CY21-25,

X 21 and R 21 are the same as described in claim 1 ,

X 22 is C(R 22 )(R 23 ), N(R 22 ), O, S, or Si(R 22 )(R 23 ),

R 22 to R 29 are the same as described in connection with R 21 in claim 1 ,

a26 is an integer from 0 to 6,

a24 is an integer from 0 to 4,

a23 is an integer from 0 to 3,

a22 is an integer from 0 to 2,

*″ is a binding site to X 2 in Formulae 2A and 2B, and

* is a binding site to Yin Formula 1.

8. The organometallic compound of claim 1 , wherein a group represented by

in Formulae 2A and 2B is a group represented by one of Formulae CY21 (1) to CY21 (56) or a group represented by one of Formulae CY21-20 to CY21-25:

wherein, in Formulae CY21 (1) to CY21 (56),

X 21 and R 21 are the same as described in claim 1 ,

R 21a to R 21a are the same as described in connection with R 21 described in claim 1 , and each of R 21 and R 21a to R 21d is not hydrogen,

*″ is a binding site to X 2 in Formulae 2A and 2B, and

* is a binding site to Y 1 in Formula 1.

9. The organometallic compound of claim 1 , wherein

a group represented by

in Formula 3D is a group represented by one of Formulae CY11-1 to CY11-34, and

a group represented by

in Formula 3D is a group represented by one of Formulae CY12-1 to CY12-34:

wherein, in Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34,

X 31 is O, S, N(Z 11 ), C(Z 11 )(Z 12 ), or Si(Z 11 )(Z 12 ),

X 41 is O, S, N(Z 21 ), C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

Y 11 , Y 12 , Z 1 , and Z 2 are the same as described in claim 1 ,

Z 11 to Z 18 and Z 21 to Z 28 are the same as described in connection with R 21 in claim 1 ,

d12 and d22 are each independently an integer from 0 to 2,

d13 and d23 are each independently an integer from 0 to 3,

d14 and d24 are each independently an integer from 0 to 4,

d15 and d25 are each independently an integer from 0 to 5,

d16 and d26 are each independently an integer from 0 to 6, and

in Formulae CY11-1 to CY11-34 and CY12-1 to CY12-34, * and *′ are each a binding site to M in Formula 1, and *″ is a binding site to T 21 in Formula 3D.

10. The organometallic compound of claim 1 , wherein L 2 in Formula 1 is represented by one of Formulae 3-1 (1) to 3-1 (66):

wherein, in Formulae 3-1 (1) to 3-1 (66),

X 41 is O, S, N(Z 21 ), C(Z 21 )(Z 22 ), or Si(Z 21 )(Z 22 ),

Z 1 to Z 2 , Z 1a , Z 1b , Z 1c , Z 1d , Z 2a , Z 2b , Z 2c , Z 2 , Z 21 , and Z 22 are the same as described in connection with R 21 in claim 1 ,

d14 and d24 are each independently an integer from 0 to 4,

d26 is an integer from 0 to 6, and

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

11. The organometallic compound of claim 1 , wherein the organometallic compound is one of Compounds 2, and 4 to 7:

12. An organic light-emitting device comprising:

a first electrode,

a second electrode; and

an organic layer between the first electrode and the second electrode,

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

13. The organic light-emitting device of claim 12 , wherein the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region located between the first electrode and the emission layer and an electron transport region located between the emission layer and the second electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

14. The organic light-emitting device of claim 12 , wherein the organometallic compound is included in the emission layer.

15. The organic light-emitting device of claim 14 , wherein the emission layer further comprises a host and the amount of the host is greater than the amount of the organometallic compound.

16. An electronic apparatus comprising the organic light-emitting device of claim 12 .

Priority Claims (1)
KR 10-2020-0018566 · Feb 14, 2020 · national
Continuity (2)
Continuation 17060677 · Oct 1, 2020
Related Publication 20240237507A1 · Jul 11, 2024
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