IP Library › Granted Patent US 12,010,909

Granted Patent B2

US 12,010,909 · App. 17/016,806 · Granted Jun 11, 2024

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

Inventors: Kyuyoung Hwang (Anyang-si, KR); Byungjoon Kang (Seoul, KR); Seungyeon Kwak (Suwon-si, KR); Kum Hee Lee (Suwon-si, KR); Aram Jeon (Seoul, KR); Sukekazu Aratani (Hwaseong-si, KR); Banglin Lee (Suwon-si, KR); Kyuhyun Im (Seongnam-si, KR); Byoungki Choi (Hwaseong-si, KR); Yasushi Koishikawa (Hwaseong-si, KR)

Assignee: SAMSUNG ELECTRONICS CO., LTD.

H10K85/342 C07F15/0033 C09K11/02 C09K11/06 C09K2211/1007 C09K2211/1029 C09K2211/1044 C09K2211/1088 C09K2211/185 H10K50/11 H10K50/15 H10K50/16 H10K50/17 H10K50/171 H10K50/18 H10K2101/10

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Quick Facts

Patent No.: US 12,010,909
App. No.: 17/016,806
Granted: Jun 11, 2024
Kind: B2

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Abstract

Provided are 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> wherein M, L 1 , L 2 , n1, and n2 in Formula 1 are the same as described in the detailed description.

Claims (184)

1. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2 <Formula 1>

wherein, in Formula 1,

M is a transition metal,

L 1 is a ligand represented by Formula 2,

L 2 is a ligand represented by Formula 3,

n1 and n2 are each independently 1 or 2, wherein when n1 is 2, two L 1 (s) are identical to or different from each other, and when n2 is 2, two L 2 (s) are identical to or different from each other,

wherein, in Formulae 2 and 3,

Y 21 is C or N,

ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

X 11 is Si or Ge,

X 1 is O, S, Se, N(Z 19 ), C(Z 19 )(Z 20 ), or Si(Z 19 )(Z 20 ),

A 21 to A 24 are each independently C or N,

L 3 is a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 2 , R 11 to R 16 , Z 1 to Z 3 , Z 19 , and Z 20 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 ), provided that Z 1 is not hydrogen,

a2 is an integer from 0 to 20, and when a2 is 2 or more, two or more R 2 (s) are identical to or different from each other,

b1 is an integer from 1 to 6, and when b1 is 2 or more, two or more Z 1 (s) are identical to or different from each other, provided that, at least one of Z 1 is 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

b2 is an integer from 0 to 4, and when b2 is 2 or more, two or more Z 2 (s) are identical to or different from each other,

R 11 and R 12 are optionally linked to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

two or more of a plurality of Z 2 (s) are optionally linked to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a is the same as defined in connection with Z 1 ,

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

a substituent 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 a C 1 -C 60 alkylthio group;

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 a C 1 -C 60 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 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, or a monovalent non-aromatic condensed heteropolycyclic 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 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 1 -C 60 alkylthio 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 ), or —P(Q 38 )(Q 39 ); 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 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, unsubstituted or substituted with deuterium, —F, 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 1 -C 60 alkylthio 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, unsubstituted or substituted with deuterium, —F, 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

ring CY 2 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a 1,2,3,4-tetrahydronaphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, or a dibenzofuran group.

3. The organometallic compound of claim 1 , wherein

L 3 in Formula 1 is:

a single bond; or

a benzene group, a naphthalene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.

4. The organometallic compound of claim 1 , wherein

R 2 , R 11 to R 13 , Z 1 to Z 3 , Z 19 and Z 20 in Formulae 2 and 3 are each independently hydrogen, deuterium, —F, or a cyano group; or

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), or any combination thereof, and

R 14 to R 16 in Formula 2 are each independently a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a naphthyl group, a pyridinyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof.

5. The organometallic compound of claim 1 , wherein

R 11 is not hydrogen.

6. The organometallic compound of claim 1 , wherein satisfying at least one of <Condition A> and <Condition B>:

L 3 is a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

Z 3 is a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

7. The organometallic compound of claim 1 , wherein

a group represented by

in Formula 2 is a group represented by one of Formulae CY2-1 to CY2-33:

wherein, in Formulae CY2-1 to CY2-33,

Y 21 and R 2 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 2 in claim 1 ,

a28 is an integer from 0 to 8,

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,

*″ indicates a binding site to a neighboring atom in Formula 2, and

* indicates a binding site to M in Formula 1.

8. The organometallic compound of claim 1 , wherein

a group represented by

in Formula 3 is a group represented by one of Formulae CY3-1 to CY3-6:

wherein, in Formulae CY3-1 to CY3-6,

X 1 , Z 1 , and b1 are the same as described in claim 1 ,

* indicates a binding site to M in Formula 1, and

*″ indicates a binding site to a neighboring atom in Formula 3.

9. The organometallic compound of claim 1 , wherein

a group represented by

in Formula 3 is a group represented by one of Formulae CY3(1) to CY3(95):

wherein, in Formulae CY3(2) to CY3(23), CY3(37) to CY3(58), and CY3(72) to CY3(93),

X 1 is the same as described in claim 1 ,

Z 11 to Z 18 are the same as described in connection with Z 1 in claim 1 , and each of Z 11 to Z 18 is not hydrogen,

Z 11 in Formulae CY3(37) and CY3(72); Z 13 in Formula CY3(2); Z 14 in Formulae CY3(3), CY3(38) and CY3(73); Z 15 in Formulae CY3(4), CY3(39) and CY3(74); Z 16 in Formulae CY3(5), CY3(40) and CY3(75); Z 17 in Formulae CY3(6), CY3(41) and CY3(76); Z 18 in Formulae CY3(7), CY3(42) and CY3(77); at least one of R 11 and R 15 in Formula CY3(43); at least one of R 11 and R 16 in Formula CY3(44); at least one of R 11 and R 17 in Formula CY3(45); at least one of R 11 and R 18 in Formula CY3(46); at least one of R 14 and R 15 in Formulae CY3(8) and CY3(78); at least one of R 14 and R 16 in Formulae CY3(9) and CY3(79); at least one of R 14 and R 17 in Formulae CY3(10) and CY3(80); at least one of R 14 and R 18 in Formulae CY3(11) and CY3(81); at least one of R 15 and R 16 in Formulae CY3(12), CY3(47) and CY3(82); at least one of R 15 and R 17 in Formulae CY3(13), CY3(48) and CY3(83); at least one of R 15 and R 18 in Formulae CY3(14), CY3(49) and CY3(84); at least one of R 16 and R 17 in Formulae CY3(15), CY3(50) and CY3(85); at least one of R 16 and R 18 in Formulae CY3(16), CY3(51) and CY3(86); at least one of R 17 and R 18 in Formulae CY3(17), CY3(52) and CY3(87); at least one of R 11 , R 15 and R 16 in Formula CY3(53); at least one of R 11 , R 15 and R 17 in Formula CY3(54); at least one of R 11 , R 15 and R 18 in Formula CY3(55); at least one of R 11 , R 16 and R 17 in Formula CY3(56); at least one of R 11 , R 16 and R 18 in Formula CY3(57); at least one of R 11 , R 17 and R 18 in Formula CY3(58); at least one of R 14 , R 15 and R 16 in Formulae CY3(18) and CY3(88); at least one of R 14 , R 15 and R 17 in Formulae CY3(19) and CY3(89); at least one of R 14 , R 15 and R 18 in Formulae CY3(20) and CY3(90); at least one of R 14 , R 16 and R 17 in Formulae CY3(21) and CY3(91); at least one of R 14 , R 16 and R 18 in Formulae CY3(22) and CY3(92); and at least one of R 14 , R 17 and R 18 in Formulae CY3(23) and CY3(93), are each independently 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

* indicates a binding site to M in Formula 1, and

*″ indicates a binding site to a neighboring atom in Formula 3.

10. The organometallic compound of claim 1 , wherein

a group represented by

in Formula 3 is a group represented by one of Formulae CY4-1 to CY4-60:

wherein, in Formulae CY4-1 to CY4-60,

L 3 and Z 3 are the same as described in claim 1 ,

Z 21 to Z 24 are the same as described in connection with Z 2 in claim 1 , and each of Z 21 to Z 24 is not hydrogen,

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

*″ indicates a binding site to a neighboring atom in Formula 3.

11. The organometallic compound of claim 1 , wherein the organometallic compound is selected from Compounds 1348, 1350, 1373, 1375, 1386 to 1410, 1428, 1448, 1450, 1461 to 1485, 1503, 1519, 1525, 1526, 1529, 1550, 1551, 1554, 1569, 1575, 1576, 1579, 1594, 1600, 1601, 1604, 2052, 2059, 2064, 2077, 2084, 2089, 2091 to 2240, 2397, 2404, 2409, 2411 to 2510 and 3111 to 3150:

12. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer located between the first electrode and the second electrode and comprising an emission layer,

wherein the organic layer comprises 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 comprises a hole transport region between the first electrode and the emission layer and an electron transport region 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 emits green light.

16. 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.

17. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2 <Formula 1>

wherein, in Formula 1,

M is a transition metal,

L 1 is a ligand represented by Formula 2,

L 2 is a ligand represented by Formula 3,

n1 and n2 are each independently 1 or 2, wherein when n1 is 2, two L 1 (s) are identical to or different from each other, and when n2 is 2, two L 2 (s) are identical to or different from each other,

wherein, in Formulae 2 and 3,

Y 21 is C or N,

ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

X 11 is Si,

X 1 is O, S, Se, N(Z 19 ), C(Z 19 )(Z 20 ), or Si(Z 19 )(Z 20 ),

A 21 to A 24 are each independently C or N,

L 3 is a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 2 , R 11 to R 16 , Z 2 , Z 3 , Z 19 , and Z 20 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 ),

Z 1 is 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, —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 ),

a2 is an integer from 0 to 20, and when a2 is 2 or more, two or more R 2 (s) are identical to or different from each other,

b1 is an integer from 0 to 6, and when b1 is 2 or more, two or more Z 1 (s) are identical to or different from each other,

b2 is an integer from 0 to 4, and when b2 is 2 or more, two or more Z 2 (s) are identical to or different from each other,

two or more of a plurality of R 2 (s) are optionally linked to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

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

R 10a is the same as defined in connection with Z 1 ,

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

provided that at least one of i) and ii) is true;

i) CY 2 is not a benzene group,

ii) at least one of A 21 to A 24 is N,

—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 ), or —P(Q 38 )(Q 39 ); 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 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, unsubstituted or substituted with deuterium, —F, 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 1 -C 60 alkylthio 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, unsubstituted or substituted with deuterium, —F, 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.

18. An organometallic compound represented by Formula 1:

M(L 1 ) n1 (L 2 ) n2 <Formula 1>

wherein, in Formula 1,

M is a transition metal,

L 1 is a ligand represented by Formula 2,

L 2 is a ligand represented by Formula 3,

n1 and n2 are each independently 1 or 2, wherein when n1 is 2, two L 1 (s) are identical to or different from each other, and when n2 is 2, two L 2 (s) are identical to or different from each other,

wherein, in Formulae 2 and 3,

Y 21 is C or N,

ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

X 11 is Ge,

X 1 is O, S, Se, N(Z 19 ), C(Z 19 )(Z 20 ), or Si(Z 19 )(Z 20 ),

A 21 to A 24 are each independently C or N,

L 3 is a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a2 is an integer from 0 to 20, and when a2 is 2 or more, two or more R 2 (s) are identical to or different from each other,

b1 is an integer from 0 to 6, and when b1 is 2 or more, two or more Z 1 (s) are identical to or different from each other,

b2 is an integer from 0 to 4, and when b2 is 2 or more, two or more Z 2 (s) are identical to or different from each other,

R 10a is the same as defined in connection with Z 1 ,

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

—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 ), or —P(Q 38 )(Q 39 ); or

any combination thereof,

19. The organometallic compound of claim 18 , wherein the organometallic compound is selected from Compounds 651 to 800, 876 to 900, 941 to 960, 1186 to 1335, 1611 to 1785, 1926 to 1945, 2591 to 2815, 2936 to 3010 and 3151 to 3190:

20. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer located between the first electrode and the second electrode and comprising an emission layer,

wherein the organic layer comprises at least one of the organometallic compound of claim 18 .

21. The organic light-emitting device of claim 20 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the organic layer comprises a hole transport region between the first electrode and the emission layer and an electron transport region 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.

22. The organic light-emitting device of claim 20 , wherein

the organometallic compound is included in the emission layer.

23. The organic light-emitting device of claim 22 , wherein

the emission layer emits green light.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2025

From: SAMSUNG ELECTRONICS CO., LTD.

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 072524/0231 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2020

From: HWANG, KYUYOUNG; KANG, BYUNGJOON; KWAK, SEUNGYEON; LEE, KUM HEE; JEON, ARAM; ARATANI, SUKEKAZU; LEE, BANGLIN; IM, KYUHYUN; CHOI, BYOUNGKI; KOISHIKAWA, YASUSHI

To: SAMSUNG ELECTRONICS CO., LTD.

Reel/Frame 053810/0612 →

Priority Claims (2)

KR 10-2019-0113025 · Sep 11, 2019 · national

KR 10-2020-0114307 · Sep 8, 2020 · national

Continuity (1)

Related Publication 20210083205A1 · Mar 18, 2021

Cited By (1)

US 12,378,468