Granted Patent B2

US 12,534,486 · App. 17/693,737 · Granted Jan 27, 2026

Inventors: Byungjoon Kang (Seoul, KR); Sangdong Kim (Seongnam-si, KR); Kum Hee Lee (Suwon-si, KR); Banglin Lee (Suwon-si, KR); Hwayoung Cho (Hwaseong-si, KR); Byoungki Choi (Hwaseong-si, KR); Kyuyoung Hwang (Anyang-si, KR)

Assignee: SAMSUNG ELECTRONICS CO., LTD.

C07F15/0033H10K85/342H10K50/11H10K2101/30H10K2101/40

Abstract

Claims (124)

1 . An organometallic compound, represented by Formula 1:

Formula 1

M(L 1 ) n1 (L 2 ) n2

wherein, in Formula 1,

M is a transition metal,

L 1 is a ligand represented by Formula 2-1,

L 2 is a ligand represented by Formula 2-2,

n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, each L 1 is identical to or different from another, and when n2 is 2, each L 2 is identical to or different from another,

a sum of n1 and n2 is 2 or 3, and

L 1 and L 2 are different from each other,

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

Y 1 and Y 4 are each independently C or N,

X 1 is Si or Ge,

X 21 is O, S, S(═O), N(Z 29 ), C(Z 29 )(Z 30 ), or Si(Z 29 )(Z 30 ),

ring CY 1 , ring CY 21 , ring CY 22 , and ring CY 14 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

A 1 is a group represented by Formula 3, provided that A 1 is not —CD 3 ,

c1 is an integer from 1 to 20,

R 21 to R 23 are each independently a C 1 -C 60 alkyl group or a C 6 -C 60 aryl group, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF 5 , —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 3 -C 10 cycloalkyl group, a phenyl group, or a combination thereof,

Z 1 to Z 5 , R 11 to R 14 , Z 29 , and Z 30 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 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl 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 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 at least one of Z 3 to Z 5 of Formula 3 is deuterium or a deuterated group,

provided that in Formula 2-2,

R 12 is hydrogen, deuterium, a methyl group, or a deuterated methyl group, or

R 12 and R 13 are linked to each other 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 ,

a1, a2, and b1 are each independently an integer from 0 to 20, and when a1 is 2 or more, two or more of Z 1 (s) are identical to or different from each other, when a2 is 2 or more, two or more of Z 2 (s) are identical to or different from each other, and when b1 is 2 or more, two or more of R 14 (s) are identical to or different from each other,

two or more of R 21 to R 23 are optionally linked to each other 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 Z 1 (s) are optionally linked to each other 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 Z 2 (s) are optionally linked to each other 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 Z 3 to Z 5 are optionally linked to each other 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 14 (s) are optionally linked to each other 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 Z 1 , Z 2 , and R 11 to R 14 are optionally linked to each other 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 as defined in connection with R 14 ,

* and *′ in Formulae 2-1 and 2-2 each indicates a binding site to M in Formula 1,

* in Formula 3 indicates a binding site to ring CY 1 in Formula 2-1,

wherein the organometallic compound satisfies at least one of Condition (1) to Condition (4);

Condition (1)

in Formula 2-1, Z 1 is not hydrogen, and a1 is an integer from 1 to 20

Condition (2)

in Formula 2-2, R 14 is not hydrogen, and b1 is an integer from 1 to 20

Condition (3)

in Formula 2-1, Z 2 is not hydrogen, and a2 is an integer from 1 to 6

Condition (4)

in Formula 2-2, X 1 is Ge, and

at least one 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 7 -C 60 alkyl aryl group, the substituted C 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, the substituted C 2 -C 60 heteroaryl alkyl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

deuterium, —F, —Cl, —Br, —I, —SF 5 , —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 at least one of deuterium, —F, —Cl, —Br, —I, —SF 5 , —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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 a 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 7 -C 60 alkyl aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, —SF 5 , —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 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 a 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

a 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, —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 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl 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 monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2 . The organometallic compound of claim 1 , wherein

in Formula 1, M is Ir, and the sum of n1 and n2 is 3; or

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

3 . The organometallic compound of claim 1 , wherein

X 21 in Formula 2-1 is O or S.

4 . The organometallic compound of claim 1 , wherein

c1 in Formula 2-1 is 1.

5 . The organometallic compound of claim 1 , wherein

ring CY 1 in Formula 2-1 is a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

6 . The organometallic compound of claim 1 , wherein

ring CY 21 in Formula 2-1 is a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a pyridine group, or a pyrimidine group.

7 . The organometallic compound of claim 1 , wherein

ring CY 22 in Formula 2-1 is a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, an anthracene group, a pyridine group, a pyrimidine group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, an azadibenzofuran group, an azadibenzothiophene group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, or a benzoquinazoline group.

8 . The organometallic compound of claim 1 , wherein

ring CY 14 in Formula 2-2 is a phenyl group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.

9 . The organometallic compound of claim 1 , wherein

Z 1 to Z 5 , R 11 , R 13 , R 14 , Z 29 , and Z 30 in Formulae 2-1 and 2-2 are each independently:

hydrogen, deuterium, —F, or a cyano group;

a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a C 2 -C 20 alkenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with at least one of 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 C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl) C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a fluorinated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a fluorinated biphenyl group, a (C 1 -C 20 alkyl) biphenyl group, —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), or a combination thereof; or

—Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).

10 . The organometallic compound of claim 1 , wherein, in Formula 3,

Z 3 is deuterium or a deuterated group, and each of Z 4 and Z 5 is a deuterium-free group;

each of Z 3 and Z 4 is deuterium or a deuterated group, and Z 5 is a deuterium-free group; or

each of Z 3 to Z 5 is deuterium or a deuterated group, provided that at least one of Z 3 to Z 5 is not deuterium.

11 . The organometallic compound of claim 1 , wherein the organometallic compound satisfies at least one of Condition (1) to Condition (3).

12 . The organometallic compound of claim 1 , wherein, in Formula 2-1,

Z 2 is not hydrogen,

a2 is an integer from 1 to 3, and

at least one of Z 2 (s) in the number of a2 is each independently a substituted or unsubstituted C 1 -C 60 alkyl 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 2 -C 20 alkenyl 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 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

13 . The organometallic compound of claim 1 , wherein

a group represented by

in Formula 2-1 is a group represented by one of Formulae CY1-1 to CY1-10:

wherein, in Formulae CY1-1 to CY1-10,

Z 11 , Z 12 , and Z 14 are as defined in connection with Z 1 of claim 1 , provided that each of Z 11 , Z 12 , and Z 14 is not hydrogen,

A 13 is as defined in connection with A 1 in claim 1 ,

ring CY 10a is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

R 10a is as defined in connection with R 10a in claim 1 ,

aa is an integer from 0 to 10,

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

*″ indicates a binding site to ring CY 21 in Formula 2-1.

14 . The organometallic compound of claim 1 , wherein

a group represented by

in Formula 2-1 is a group represented by one of Formulae CY2-1 to CY2-6:

wherein, in Formulae CY2-1 to CY2-6,

T 1 to T 8 are each independently C or N,

X 21 is as defined in claim 1 ,

*″ indicates a binding site to ring CY 1 in Formula 2-1, and

*′ indicates a binding site to M in Formula 1.

15 . The organometallic compound of claim 1 , wherein

a group represented by

in Formula 2-2 is a group represented by one of Formulae CY14(1) to CY14(63):

wherein, in Formulae CY14(1) to CY14(63),

R 14a to R 14a are as defined in connection with R 14 in claim 1 , provided that each of R 14a to R 14d is not hydrogen,

X 14 is C(R 1 )(R 2 ), N(R 1 ), O, S, or Si(R 1 )(R 2 ),

R 1 to R 8 are as defined in connection with R 14 in claim 1 ,

*″ indicates a binding site to a carbon atom of a neighboring pyridine ring in Formula 2-2, and

*′ indicates a binding site to M in Formula 1.

16 . 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,

wherein the organic layer comprises an emission layer, and

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

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

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

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

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

the emission layer comprises the at least one of the organometallic compound.

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

the emission layer further comprises a host, and

an amount of the host in the emission layer is greater than an amount of the organometallic compound in the emission layer.

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

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (37)