Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
An organometallic compound, represented by Formula 1: M(L 1 ) n1 (L 2 ) n2 Formula 1 wherein 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 is 0, 1, or 2, n2 is 1, 2, or 3, and L 1 and L 2 are different from each other, wherein R 1 to R 4 , rings CY 1 to CY 3 , rings CY 41 and CY 42 , Y 1 to Y 3 , X 4 , Z 4 , a1 to a3, b4, *, and *′ are each as defined herein.
1. An organometallic compound, represented by Formula 1:
M(L 1 )n 1 (L 2 )n 2 Formula 1
wherein, in Formula 1,
M is a transition metal,
L 1 is a ligand represented by Formula 2-1,
n1 is 0, 1, or 2, wherein, when n1 is 2 the two L 1 are identical to or different from each other,
L 2 is a ligand represented by Formula 2-2,
n2 is 1, 2, or 3, wherein, when n2 is 2 or more, two or more L 2 ( s ) are identical to or different from each other, and
L 1 and L 2 are different from each other,
wherein, Y 1 and Y 2 in Formula 2-1 are each independently C or N,
Y 3 in Formula 2-2 is N,
a bond between Y 3 in Formula 2-2 and M in Formula 1 is a coordinate bond,
ring CY 1 , CY 2 , and ring CY 3 in Formulae 2-1 and 2-2 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
ring CY 41 and ring CY 42 in Formula 2-2 are each independently a π electron-rich C 5 -C 30 cyclic group,
a carbon atom of ring CY 41 in Formula 2-2 and M in Formula 1 are bonded to each other via a covalent bond,
X 4 in Formula 2-2 is O, S, Se, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ),
Z 4 in Formula 2-2 is a group represented by Formula 3,
-(T 4 ) c4 -Y 4 (Q 41 )(Q 42 )(Q 43 ) Formula 3
b4 in Formula 2-2 is an integer from 1 to 20,
Y 4 in Formula 3 is Si or Ge,
T 4 in Formula 3 is a single bond, 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 ,
when T 4 is not a single bond, c4 in Formula 3 is an integer from 1 to 10,
R 1 to R 4 , R 48 , R 49 , and Q 41 to Q 43 in Formulae 2-1, 2-2, and 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, 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 2 -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 to a4 in Formulae 2-1 and 2-2 are each independently an integer from 0 to 20, wherein when CY 1 and CY 3 are each a pyridine group and CY 2 is a benzene group one of the following is satisfied:
i) a1 is 1 or more, and at least one of R 1 (s) in a number of a1 is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 );
ii) a2 is 2 or more, and at least one of R 2 (s) in a number of a2 is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 );
R 10a is the same as described in connection with R 2 ,
* and *′ in Formulae 2-1 and 2-2 each indicate a binding site to M in Formula 1,
* in Formula 3 indicates a binding site to a neighboring atom,
two or more of a plurality of R 1 (s) in Formula 2-1 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 2 (s) in Formula 2-1 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 3 (s) in Formula 2-2 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 4 (s) in Formula 2-2 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 R 1 to R 4 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 ,
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 2 -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, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro 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;
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, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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 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 2 -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 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 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, 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 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alky 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 ); 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: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alky 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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, a C 1 -C 60 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alky 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, or a combination thereof.
2. The organometallic compound of claim 1 , wherein ring CY 1 and ring CY 3 are each independently a pyridine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a naphthoquinoline group, a naphthoisoquinoline group, a naphthoquinoxaline group, a pyridine group condensed with a cyclohexane group, a pyridine group condensed with a norbornane group, an imidazole group, a benzimidazole group, a naphthoimidazole group, or a phenanthrenoimidazole group.
3. The organometallic compound of claim 1 , wherein ring CY 2 is a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a 1,2,3,4-tetrahydronaphthalene group, a benzene group condensed with a norbornane group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, or a dibenzoselenophene group.
4. The organometallic compound of claim 1 , wherein ring CY 41 and ring CY 42 are each independently:
i) a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, or a triphenylene group; or
ii) a polycyclic group wherein at least one benzene group and at least one B group are condensed with each other, wherein
the at least one B group is a cyclohexane group, a norbornane group, a furan group, a thiophene group, a selenophene group, a pyrrole group, a cyclopentadiene group, or a silole group.
5. The organometallic compound of claim 1 , wherein b4 is 1 or 2.
6. The organometallic compound of claim 1 , wherein R 1 to R 4 , R 48 , and R 49 are each independently:
hydrogen, deuterium, —F, or a cyano group;
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 a combination thereof; or
—Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).
7. The organometallic compound of claim 1 , wherein, in Formula 2-1,
i) a1 is 1 or more, and at least one of R 1 (s) in a number of a1 is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).
8. 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 CY1-25:
wherein, in Formulae CY1-1 to CY1-25,
Y 1 is as defined in claim 1 ,
X 1 is O, S, Se, N(R 18 )(R 19 ), C(R 18 )(R 19 ), or Si(R 18 )(R 19 ),
R 18 and R 19 are each as defined in connection with R 1 in claim 1 ,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to a neighboring atom in Formula 2-1.
9. 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(16):
wherein, in Formulae CY1(1) to CY1(16),
Y 1 is as defined in claim 1 ,
R 11 to R 14 are each as defined in connection with R 1 in claim 1 , wherein each of R 11 to R 14 is not hydrogen,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to a neighboring atom in Formula 2-1.
10. 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 CY2-50:
wherein, in Formulae CY2-1 to CY2-50,
Y 2 is as defined in claim 1 ,
X 2 is O, S, Se, N(R 28 ), C(R 28 )(R 29 ), or Si(R 28 )(R 29 ),
R 28 and R 29 are each as defined in connection with R 2 in claim 1 ,
*″ indicates a binding site to a neighboring atom in Formula 2-1, and
*indicates a binding site to M in Formula 1.
11. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-2 is a group represented by one of Formulae CY3-1 to CY3-33:
wherein, in Formulae CY3-1 to CY3-33,
Y 3 is as defined in claim 1 ,
X 3 is O, S, Se, N(R 38 ), C(R 38 )(R 39 ), or Si(R 38 )(R 39 ),
R 38 and R 39 are each as defined in connection with R 3 in claim 1 ,
*′ indicates a binding site to M in Formula 1, and
*″ indicates a binding site to a neighboring atom in Formula 2-2.
12. The organometallic compound of claim 1 , wherein a group represented by
in Formula 2-2 is represented by one of Formulae CY4-1 to CY4-6:
wherein, in Formulae CY4-1 to CY4-6,
X 4 and ring CY 42 are as defined in claim 1 ,
*indicates a binding site to M in Formula 1, and
*″ indicates a binding site to ring CY 3 in Formula 2-2.
13. The organometallic compound of claim 1 , wherein a group represented by
in the structure of
in Formula 2-2 is represented by one of Formulae CY401 to CY413:
wherein, in Formulae CY401 to CY413,
X 4 is as defined in claim 1 , and
an X 4 -containing 5-membered ring is condensed with a neighboring ring CY 41 .
14. The organometallic compound of claim 1 , wherein ring CY 42 in Formula 2-2 is substituted with at least one of Z 4 .
15. 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 comprises at least one of the organometallic compound of claim 1 .
16. The organic light-emitting device of claim 15 , 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 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.
17. The organic light-emitting device of claim 15 , wherein the emission layer comprises the at least one of the organometallic compound.
18. The organic light-emitting device of claim 17 , wherein the emission layer emits green light.
19. The organic light-emitting device of claim 17 , 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 at least one of the organometallic compound in the emission layer.
20. An electronic apparatus, comprising the organic light-emitting device of claim 15 .
21. The organometallic compound of claim 1 , wherein
M may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh); and
a3 is one or more and at least one R 3 is —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, a group represented by one of Formulae 9-1 to 9-39, a group represented by one of Formulae 9-1 to 9-39 wherein at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-1 to 9-39 wherein at least one hydrogen is substituted with —F, a group represented by one of Formulae 9-201 to 9-230, a group represented by one of Formulae 9-201 to 9-230 wherein at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 9-201 to 9-230 wherein at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-1 to 10-145, a group represented by one of Formulae 10-1 to 10-145 wherein at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-145 wherein at least one hydrogen is substituted with —F, a group represented by one of Formulae 10-201 to 10-354, a group represented by one of Formulae 10-201 to 10-354 wherein at least one hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-354 wherein at least one hydrogen is substituted with —F,
wherein * indicates a binding site to ring CY 3 , Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and OMe is a methoxy group.
22. An organometallic compound of claim 1 , wherein
a2 is 2 or more, and at least one of R 2 (s) in a number of a2 is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).