Organic light-emitting device and electronic apparatus including the same
Provided are an organic light-emitting device including a first compound, a second compound, and a third compound, and an electronic apparatus including the same. The organic light-emitting device includes a first electrode; a second electrode facing the first electrode; and an emission layer disposed between the first electrode and the second electrode, the emission layer including the first compound, the second compound, and the third compound.
1 . An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an emission layer disposed between the first electrode and the second electrode;
the emission layer comprises a first compound, a second compound, and a third compound,
the first compound, the second compound, and the third compound are different from one another,
an amount of the first compound is smaller than a total amount of the second compound and the third compound,
the first compound is a compound represented by Formula 1,
the second compound comprises at least one group selected from a pyrimidine group, and a triazine group and at least one Si,
the third compound comprises at least one of a compound represented by Formula 3-1, a compound represented by Formula 3-2, a compound represented by Formula 3-3, a compound represented by Formula 3-4, and a compound represented by Formula 3-5,
the first compound and the second compound form an exciplex, and
a decay time of delayed fluorescence in a time-resolved electroluminescence (TREL) spectrum of the organic light-emitting device is 50 ns or more:
wherein, in Formula 1,
M is Pt,
X 1 is N,
X 2 to X 4 are C,
T 11 to T 14 are a chemical bond,
T 1 and T 3 are a single bond,
T 2 are *—N(R 6 )—**, *—C(R 6a )(R 6b )—**, *—Si(R 6a )(R 6b )—**, *—S—**, or *—O—**,
a moiety represented by
is a group represented by Formula A1-1(1),
a moiety represented by
is a group represented by Formula A2-2(1),
a moiety represented by
is a group represented by Formula A3-1(1),
a moiety represented by
is represented by Formula A4-1(27),
R 1 to R 4 , R 6 , R 6a , and R 6b are each independently selected from 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 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 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), and —S(═O) 2 (Q 1 ),
a14 is an integer of 0 to 4,
a26 is an integer of 0 to 6,
a33 is an integer of 0 to 3,
a45 is an integer of 1 to 5,
provided that, at least one of R 4 is selected from 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 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 C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
* in Formula A1-1(1) indicates a binding site to M in Formula 1,
*′ in Formula A1-1(1) indicates a binding site to T 1 in Formula 1,
* in Formula A2-2(1) indicates a binding site to M in Formula 1,
*′ in Formula A2-2(1) indicates a binding site to T 1 in Formula 1,
*″ in Formula A2-2(1) indicates a binding site to T 2 in Formula 1,
* in Formula A3-1(1) indicates a binding site to M in Formula 1,
*′ in Formula A3-1(1) indicates a binding site to T 3 in Formula 1,
*″ in Formula A3-1(1) indicates a binding site to T 2 in Formula 1,
* in A4-1(27) indicates a binding site to M in Formula 1,
*′ in A4-1(27) indicates a binding site to T 3 in Formula 1,
i) two groups selected from R 1 (s) in the number of a14, ii) two groups selected from R 2 (s) in the number of a26, iii) two groups selected from R 3 (s) in the number of a33, iv) two groups selected from R 4 (s) in the number of a45, and v) R 6a and R 6b , are optionally linked via a single bond, a double bond, or a first linking group 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 , provided that R 3 and R 4 are not linked,
wherein in Formula 3-1 to 3-5,
ring CY 71 to ring CY 74 are each independently selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, an indene group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzothiophene group, an azabenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and a pyridine group,
L 81 is selected from *—C(Q 4 )(Q 5 )-**, *—Si(Q 4 )(Q 5 )-**, a substituted or unsubstituted C 5 -C 30 carbocyclic group, and a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b81 is an integer of 0 to 5,
X 81 is a single bond, O, S, N(R 81 ), B(R 81 ), C(R 81a )(R 81b ), or Si(R 81a )(R 81b ),
X 82 is a single bond, O, S, N(R 82 ), B(R 82 ), C(R 82a )(R 82b ), or Si(R 82a )(R 82b ),
X 83 is a single bond, O, S, N(R 83 ), B(R 83 ), C(R 83a )(R 83b ), or Si(R 83a )(R 83b ),
X 84 is C or Si,
R 71 to R 74 , R 80 to R 83 , R 81a , R 81b , R 82a , R 82b , R 83a , R 83b , and R 84 are each independently be selected from 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 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 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(=O)(Q 1 )(Q 2 ),
a71 to a74 are each independently an integer of 0 to 10,
two groups selected from R 71 to R 74 , R 80 to R 83 , R 81a , R 81b , R 82a , R 82b , R 83a , R 83b , and R 84 are optionally linked via a single bond, a double bond, or a first linking group 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 ,
wherein in Formulae 1 and 3-1 to 3-5,
R 10a is the same as defined in connection with R 1 ,
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 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 C 2 -C 60 alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and 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, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —O(Q 11 ), —S(Q 11 ), —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —P(Q 11 )(Q 12 ), —C(═O)(Q 11 ), and —S(=O) 2 (Q 11 );
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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 6 -Coo 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 monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —O(Q 21 ), —S(Q 21 ), —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —P(Q 21 )(Q 22 ), —C(═O)(Q 21 ), and —S(═O) 2 (Q 21 ); and
—O(Q 31 ), —S(Q 31 ), —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), and —S(═O) 2 (Q 31 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from 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 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 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, a C 1 -C 60 alkyl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a phenyl group, and a biphenyl group, and a C 6 -C 60 aryl group substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 10 alkyl group, a phenyl group, and a biphenyl group.
2 . The organic light-emitting device of claim 1 , wherein:
the organic light-emitting device has a non-resonance structure,
an electroluminescence (EL) spectrum of the organic light-emitting device includes a first peak and a second peak,
a maximum emission wavelength of the second peak is greater than a maximum emission wavelength of the first peak,
a difference between the maximum emission wavelength of the second peak and the maximum emission wavelength of the first peak is in a range of about 5 nm to about 30 nm, and
the intensity of the second peak is smaller than the intensity of the first peak.
3 . The organic light-emitting device of claim 2 , wherein:
the maximum emission wavelength of the first peak is in a range of about 390 nm to about 500 nm.
4 . The organic light-emitting device of claim 2 , wherein:
the first peak is an emission peak of phosphorescence emitted from the first compound, and
the second peak is an emission peak of an exciplex formed by the first compound and the second compound.
5 . The organic light-emitting device of claim 2 , wherein:
the intensity of the second peak is in a range of about 20% to about 90% of the intensity of the first peak.
6 . An electronic apparatus comprising the organic light-emitting device of claim 1 .
7 . The electronic apparatus of claim 6 , further comprising a thin film transistor comprising a source electrode and a drain electrode,
wherein the first electrode of the organic light-emitting device is electrically coupled to the source electrode or the drain electrode.
8 . The organic light-emitting device of claim 1 , wherein:
the organic light-emitting device satisfies at least one of Condition 1 to Condition 4:
Condition 1
a lowest unoccupied molecular orbital (LUMO) energy level (eV) of the third compound>a LUMO energy level (eV) of the first compound
Condition 2
the LUMO energy level (eV) of the first compound>a LUMO energy level (eV) of the second compound
Condition 3
a highest occupied molecular orbital (HOMO) energy level (eV) of the first compound>a HOMO energy level (eV) of the third compound
Condition 4
the HOMO energy level (eV) of the third compound>a HOMO energy level (eV) of the second compound.
9 . The organic light-emitting device of claim 1 , wherein:
an absolute value of a difference between a lowest unoccupied molecular orbital (LUMO) energy level of the first compound and a LUMO energy level of the second compound is 0.1 eV to 1.0 eV.
10 . The organic light-emitting device of claim 1 , wherein:
an absolute value of a difference between a lowest unoccupied molecular orbital (LUMO) energy level of the first compound and a LUMO energy level of the third compound is 0.1 eV to 1.0 eV.
11 . The organic light-emitting device of claim 1 , wherein:
an absolute value of a difference between a highest occupied molecular orbital (HOMO) energy level of the first compound and a HOMO energy level of the second compound is 1.25 eV or less.
12 . The organic light-emitting device of claim 1 , wherein:
an absolute value of a difference between a highest occupied molecular orbital (HOMO) energy level of the first compound and a HOMO energy level of the third compound is 1.25 eV or less.
13 . The organic light-emitting device of claim 1 , wherein:
the third compound comprises at least two carbazole groups.