Organometallic compound, organic light-emitting device including the organometallic compound, and diagnosis composition including the organometallic compound
An organometallic compound is represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification. The organometallic compound represented by Formula 1 provides high photoluminescent efficiency and is useful in organic light-emitting devices or as a diagnostic composition (e.g., various applications including a diagnosis kit a diagnosis reagent, a biosensor, or a biomarker).
1. 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,
wherein the organic layer comprises an emission layer, and
wherein the organic layer comprises at least one organometallic compound represented by one selected from Formulae 1-1 to 1-4:
wherein, in Formulae 1-1 to 1-4,
M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
X 1 is O or S, and a bond between X 1 and M is a covalent bond,
X 11 is N or C(R 11 ), X 12 is N or C(R 12 ), X 13 is N or C(R 13 ), and X 14 is N or C(R 14 ),
X 21 is N or C(R 21 ), X 22 is N or C(R 22 ), and X 23 is N or C(R 23 ),
X 31 is N or C(R 31 ), X 33 is N or C(R 33 ), X 34 is N or C(R 34 ), X 35 is N or C(R 35 ), X 36 is N or C(R 36 ), and X 37 is N or C(R 37 ),
X 39 is C(R 39a )(R 39b ), N(R 39 ), O, S, Se, or Si(R 39a )(R 39b ),
X 41 is N or C(R 41 ), X 42 is N or C(R 42 ), X 43 is N or C(R 43 ), and X 44 is N or C(R 44 ), provided that the ring of Formulae 1-1 to 1-4 having the X 41 to X 44 groups is not a pyrimidine,
T 1 to T 3 are each independently selected from *—S—*′, *—C(R 5 )(R 6 )—*′, *—C(R 5 )═*′, *═C(R 5 )—*′, *—C(R 5 )═C(R 6 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C═C—*′, *—Si(R 5 )(R 6 )—*′, *—Ge(R 5 )(R 6 )—*′, *—B(R 5 )—*′, *—N(R 5 )—*′, and *—P(R 5 )—*′,
R 5 and R 6 are optionally linked to each other via a first linking group to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b1 to b2 are each independently 0, 1, 2, or 3, and b3 is 0 or 1, wherein when b1 is zero, *-(T 1 ) b1 -*′ is a single bond, when b2 is zero, *-(T 2 ) b2 -*′ is a single bond, and when b3 is zero, *-(T 3 ) b3-*′ is a single bond,
provided that when T 3 is *—C(R 5 )(R 6 )—*′, then R 5 and R 6 are not linked,
provided that at least one of X 33 -X 37 in Formulae 1-1 and 1-2 is N, and at least one of X 31 , X 34 , X 35 , X 36 , and X 37 in Formulae 1-3 and 1-4 is N,
R 5 , R 6 , R 11 to R 14 , R 21 to R 23 , R 31 , R 33 , R 34 to R 37 , R 39 , R 39a , R 39b and R 41 to R 44 are each independently selected from
hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a cyano group, a nitro group, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
—N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),
wherein Q 1 to Q 9 are each independently selected from:
—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, and —CD 2 CDH 2 ;
an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C 1 -C 10 alkyl group, and a phenyl group,
two of R 11 to R 14 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, provided that the condensed ring comprising the ring having the X 11 to X 14 groups and the C 5 -C 30 carbocyclic group fromed by the R 11 to R 14 groups is not a naphthyl group,
two of R 21 to R 23 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two of R 34 to R 37 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, and
two of R 41 to R 44 may optionally be linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, provided that the condensed ring comprising the ring having the X 41 to X 44 groups and the C 5 -C 30 carbocyclic group formed by the R 41 to R 44 groups is not a quinoline group.
2. The organic light-emitting device of claim 1 , wherein T 1 to T 3 are each independently selected from *—S—*′, *—C(R 5 )(R 6 )—*′, *—Si(R 5 )(R 6 )—*′, *—N(R 5 )—*′, and *—P(R 5 )—*′.
3. The organic light-emitting device of claim 1 , wherein
b1, b2, and b3 are each zero;
b1 is one, and b2 and b3 are each zero;
b2 is one, and b1 and b3 are each zero; or
b3 is one, and b1 and b2 are each zero.
4. The organic light-emitting device of claim 1 , wherein
X 22 is C(R 22 ) and R 22 is not hydrogen.
5. The organic light-emitting device of claim 1 , wherein
at least one of X 34 to X 37 in Formulae 1-3 and 1-4 is N.
6. The organic light-emitting device of claim 1 , wherein R 5 , R 6 , R 11 to R 14 , R 21 to R 23 , R 31 , R 33 , R 34 to R 37 , R 39 , R 39a , R 39b and R 41 to R 44 are each independently selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF 5 , —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-46, and —Si(Q 3 )(Q 4 )(Q 5 ):
wherein * in Formulae 9-1 to 9-19 and 10-1 to 10-46 indicates a binding site to a neighboring atom.
7. An organometallic compound of Compound 5 or 6:
8. The organic light-emitting device of claim 1 , wherein
the first electrode is an anode,
the second electrode is a cathode, and
the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed 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, 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.
9. The organic light-emitting device of claim 1 , wherein the emission layer comprises the organometallic compound.
10. The organic light-emitting device of claim 1 , wherein the emission layer further comprises a host, and an amount by weight of the host in the emission layer is larger than an amount by weight of the organometallic compound in the emission layer.
11. A diagnostic composition comprising at least one of the organometallic compounds of claim 7 .