Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
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: wherein, in Formula 1, Y 2 , ring CY 1 , ring CY 2 , T 1 , T 2 , A 1 to A 7 , a1, and a2 are as defined in the specification.
1. An organometallic compound represented by Formula 1,
wherein, in Formula 1,
Y 2 is C or N,
a group represented by
in Formula 1 is one of groups represented by Formulae CY1(1)-1 to CY1(1)-64, CY1(6)-2 to CY1(6)-8, and CY1(6)-10 to CY1(6)-16:
wherein, in Formulae CY1(1)-1 to CY1(1)-64, and CY1(6)-2 to CY1(6)-8 and CY1(6)-10 to CY1(6)-16,
indicates a binding site to Ir in Formula 1, and
*″ indicates a binding site to ring CY 2 in Formula 1,
ring CY 2 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
T 1 , T 2 and A 1 to A 7 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 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 ),
T 11 to T 18 are the same as defined in connection with T 1 , provided that each of Ti to T 18 is not hydrogen, T 101 to T 108 in Formulae CY1(1)-1 to CY1(1)-64 each comprises at least one fluoro group (—F) and T 106 and T 107 in Formulae CY1(6)-2 to CY1(6)-8 and CY1(6)-10 to CY1(6)-16 each comprises a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, a fluorinated biphenyl group, or a fluorinated terphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof,
a1 and a2 are each independently an integer of 0 to 20; when al is 2 or greater, two or more T 1 (s) are identical to or different from each other; when a2 is 2 or greater, two or more T 2 (s) are identical to or different from each other; and the sum of a1 and a2 is 1 or greater,
two or more of Ti(s) in the number of a1 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of T 2 ( s ) in the number of a2 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
T 1 and T 2 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
two or more of A 1 to A 7 are optionally linked to one another to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
R 1a is the same as defined in connection with A 7 ,
a substituent(s) 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 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 are each independently:
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 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, or a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each substituted with deuterium, —F, —C 1 , —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 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 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 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 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 monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —C 1 , —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 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 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 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,
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, 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 2 -C 10 heterocycloalkenyl group; a C 6 -C 60 aryl group 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 the ring CY2 is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.
3. The organometallic compound of claim 1 , wherein T 1 , T 2 , and A 1 to A 7 are each independently hydrogen, deuterium, —F, a substituted or unsubstituted C 1 -C 20 alkyl 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 a phenyl group, a substituted or unsubstituted a biphenyl group, a substituted or unsubstituted a terphenyl group, —Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ).
4. The organometallic compound of claim 1 , wherein T 1 , and A 1 to A 7 are each independently:
hydrogen, deuterium, —F, C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, or a terphenyl group;
a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, a fluorinated biphenyl group, or a fluorinated terphenyl group, each unsubstituted or substituted with deuterium, C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof;
a deuterated C 1 -C 20 alkyl group, a deuterated C 3 -C 10 cycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a deuterated phenyl group, a deuterated biphenyl group, or a deuterated terphenyl group, each unsubstituted or substituted with —F, C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof, or
—Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ).
5. The organometallic compound of claim 1 , wherein T 2 does not comprise —F and a cyano group.
6. The organometallic compound of claim 1 , wherein T 2 , and A 1 to A 7 are each independently:
hydrogen, deuterium, C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, or a terphenyl group;
a deuterated C 1 -C 20 alkyl group, a deuterated C 3 -C 10 cycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a deuterated phenyl group, a deuterated biphenyl group, or a deuterated terphenyl group, each unsubstituted or substituted with a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any 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 Formulae CY1(1)-1 to CY1(1)-64, CY1(6)-2 to CY1(6)-8, and CY1(6)-10 to CY1(6)-16,
T 11 to T 18 are each independently:
deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, or a terphenyl group;
a deuterated C 1 -C 20 alkyl group, a deuterated C 3 -C 10 cycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a deuterated phenyl group, a deuterated biphenyl group, or a deuterated terphenyl group, each unsubstituted or substituted with a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof, or
—Si(Q 3 )(Q 4 )(Q 5 ), or —Ge(Q 3 )(Q 4 )(Q 5 ), and
T 101 to T 108 in Formulae CY1(1)-1 to CY1(1)-64 are each independently:
—F; or
a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, a fluorinated biphenyl group, or a fluorinated terphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof,
T 106 and T 107 in Formulae CY1(6)-1 to CY1(6)-16 are each independently:
a fluorinated C 1 -C 20 alkyl group, a fluorinated C 3 -C 10 cycloalkyl group, a fluorinated C 1 -C 10 heterocycloalkyl group, a fluorinated phenyl group, a fluorinated biphenyl group, or a fluorinated terphenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
8. The organometallic compound of claim 1 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY2-1 to CY2-31:
wherein, in Formulae CY2-1 to CY2-31,
Y 2 and T 2 are the same as defined in claim 1 ,
X 22 is C(T 28 )(T 29 ), N(T 28 ), O, S or Si (T 28 )(T 29 ),
T 22 to T 29 are the same as defined in connection with T 2 in claim 1 ,
a26 is an integer of 0 to 6,
a25 is an integer of 0 to 5,
a24 is an integer of 0 to 4,
a23 is an integer of 0 to 3,
a22 is an integer of 0 to 2,
*″ indicates a binding site to ring CY 1 in Formula 1, and
*′ indicates a binding site to Ir in Formula 1.
9. The organometallic compound of claim 1 , wherein a group represented by
in Formula 1 is one of groups represented by Formulae CY2(1) to CY2(68):
wherein, in Formulae CY2(1) to CY2(68),
Y 2 is the same as defined in claim 1 ,
X 22 is C (T 28 )(T 29 ), N(T 28 ), O, S, or Si (T 28 )(T 29 ),
T 21 to T 25 , T 28 , and T 29 are the same as defined in connection with T 2 in claim 1 , but each of
T 21 to T 24 are not hydrogen,
*″ indicates a binding site to ring CY 1 in Formula 1, and
*′ indicates a binding site to Ir in Formula 1.
10. The organometallic compound of claim 1 , wherein the organometallic compound satisfies at least one of Condition 1 to Condition 3:
Condition 1
A 1 to A 6 in Formula 1 are each independently 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 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -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;
Condition 2
at least one of A 1 to A 6 in Formula 1 are each independently a substituted or unsubstituted C 2 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -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; and
Condition 3
A 7 in Formula 1 is deuterium, 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 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 2 -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.
11. The organometallic compound of claim 1 , wherein the organometallic compound satisfies at least one of Condition 4 and Condition 5:
Condition 4
in Formula 1, two or more of A 1 to A 3 of the group represented by *—C(A 1 )(A 2 )(A 3 ) are linked with C in the group represented by *—C(A 1 )(A 2 )(A 3 ) to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a so that the group represented by *—C(A 1 )(A 2 )(A 3 ) is a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a ,
Condition 5
in Formula 1, two or more of A 4 to A 6 of the group represented by *—C(A 4 )(A 5 )(A 6 ) are linked with C in the group represented by *—C(A 4 )(A 5 )(A 6 ) to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one Ria so that the group represented by *—C(A 4 )(A 5 )(A 6 ) is a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 1a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 1a .
12. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer, the organic layer comprising at least one organometallic compound represented by Formula 1 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 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 in the emission layer.
15. The organic light-emitting device of claim 14 , wherein the emission layer further comprises a host, and an amount of the host in the emission layer is larger than an amount of the organometallic compound in the emission layer.
16. An electronic apparatus comprising the organic light-emitting device of claim 12 .