Organic light-emitting device
An organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, wherein the emission layer includes an electron transport host, a hole transport host, and a dopant, wherein the dopant includes an organometallic compound, and wherein the organometallic compound does not comprise iridium, wherein the organic light-emitting device satisfies predetermined parameters described in the specification.
1. An organic light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode, and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer, and the emission layer comprises an electron transport host, a hole transport host, and a dopant,
wherein the dopant comprises an organometallic compound, and the organometallic compound does not comprise iridium,
wherein the organic light-emitting device satisfies a condition of LUMO(dopant)−LUMO(host-E)≥0.15 eV and LUMO (host-E)−HOMO(host-H)>T1(dopant), and
LUMO(dopant) indicates a lowest unoccupied molecular orbital (LUMO) energy level (expressed in electron volts) of the dopant in the emission layer,
LUMO (host-E) indicates a LUMO energy level (expressed in electron volts) of the electron transport host in the emission layer,
HOMO(host-H) indicates a highest occupied molecular orbital (HOMO) energy level (expressed in electron volts) of the hole transport host in the emission layer,
T1(dopant) indicates a triplet energy level (expressed in electron volts) of the dopant in the emission layer, and
LUMO(dopant), LUMO (host-E), and HOMO(host-H) each indicate a negative value measured by differential pulse voltammetry using ferrocene as a reference material, and
T1(dopant) is a value calculated from a peak wavelength of a phosphorescence spectrum of the dopant measured using a luminescence measuring device,
wherein the dopant includes a metal M and a ligand represented by Formula 1-3 and the the metal M is platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), ruthenium (Ru), rhenium (Re), beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), palladium (Pd), silver (Ag), or gold (Au):
wherein in Formula 1-3,
A 1 to A 4 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group, a substituted or unsubstituted C 1 -C 30 heterocyclic group, or a non-cyclic group,
Y 11 to Y 14 are each independently a chemical bond, O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ), and at least one of Y 11 to Y 14 are each independently O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ),
T 1 to T 4 are each independently a single bond, a double bond, *—N(R 93 )—*′, *—B(R 93 )—*′, *—P(R 93 )—*′, *—C(R 93 )(R 94 )—*′, *—Si(R 93 )(R 94 )—*′, *—Ge(R 93 )(R 94 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(—O) 2 —*′, *—C(R 93 )—*′, *—C(R 93 )—*′, *—C(R 93 )═C(R 94 )—*′, *—C(═S)—*′, or *—C≡C—*′,
wherein a substituent of the substituted C 5 -C 30 carbocyclic group, a substituent of the substituted C 1 -C 30 heterocyclic group, and R 91 to R 94 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl 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 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ), and with a proviso that the substituent of the substituted C 5 -C 30 carbocyclic group and the substituent of the substituted C 1 -C 30 heterocyclic group are not hydrogen,
Q 1 to Q 9 are each independently: —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, or —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, or a naphthyl group; or
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, or a naphthyl group, each of which is substituted with at least one of deuterium, a C 1 -C 10 alkyl group, or a phenyl group, and
*1, *2, *3, and *4 each indicate a binding site to M of the dopant.
2. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of 0.15 eV≤LUMO(dopant)−LUMO (host-E)≤0.6 electron volts.
3. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of 0 electron volts <[LUMO (host-E)−HOMO(host-H)]−T1(dopant)≤0.5 electron volts.
4. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO(dopant)<LUMO (host-H), wherein LUMO (host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.
5. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO (host-E)<LUMO (host-H), wherein LUMO (host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.
6. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of LUMO (host-E)<LUMO(dopant)<LUMO (host-H), wherein LUMO (host-H) indicates a LUMO energy level (expressed in electron volts) of the hole transport host in the emission layer, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.
7. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of HOMO(host-E)<HOMO(host-H).
8. The organic light-emitting device of claim 1 , wherein the dopant is an organometallic compound having a square-planar coordination structure.
9. The organic light-emitting device of claim 1 , wherein the dopant satisfies a condition of T1(dopant)≤Egap(dopant)≤T1(dopant)+0.5 electron volts,
wherein Egap (dopant) is a difference between HOMO (dopant) and LUMO(dopant) of the dopant, and
HOMO (dopant) indicates a HOMO energy level of the dopant, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.
10. The organic light-emitting device of claim 1 , wherein the organic light-emitting device satisfies a condition of −2.8 electron volts≤LUMO(dopant)≤−2.3 electron volts and −6.0 electron volts≤HOMO (dopant)≤−4.5 electron volts, wherein HOMO (dopant) indicates a HOMO energy level of the dopant, which is a negative value measured by differential pulse voltammetry using ferrocene as a reference material.
11. The organic light-emitting device of claim 1 , wherein the electron transport host comprises at least one electron transport moiety, and wherein the hole transport host does not comprise an electron transport moiety,
wherein the electron transport moiety is selected from a cyano group, a n electron-depleted nitrogen-containing cyclic group, and groups represented by the following formulae:
wherein *, *′, and *″ in the formulae above each indicate a binding site to a neighboring atom.
12. The organic light-emitting device of claim 1 , wherein the electron transport host has a lowest anion decomposition energy of 2.5 electron volts or more.
13. The organic light-emitting device of claim 1 , wherein the electron transport host comprises at least one π electron-depleted nitrogen-free cyclic group and at least one electron transport moiety, and
wherein the hole transport host comprises at least one π electron-depleted nitrogen-free cyclic group and does not comprise an electron transport moiety.
14. The organic light-emitting device of claim 1 , further comprising a hole transport region disposed between the first electrode and the emission layer,
wherein the hole transport region comprises an amine-containing compound.
15. An organic light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode, and
light-emitting units in a number of m that are stacked between the first electrode and the second electrode,
wherein the light-emitting units comprise at least one emission layer, wherein m is an integer of greater than or equal to 2,
wherein a maximum emission wavelength of light emitted by at least one of the light-emitting units in the number of m is different from a maximum emission wavelength of light emitted by at least one of the other light-emitting units,
wherein the emission layer includes an electron transport host, a hole transport host, and a dopant, and the dopant includes an organometallic compound, provided that the organometallic compound does not include iridium, and
wherein the organic light-emitting device satisfies a condition of LUMO(dopant)−LUMO(host-E)≥0.15 electron volts and LUMO (host-E)−HOMO(host-H)>T1(dopant),
wherein
LUMO(dopant) indicates a LUMO energy level (expressed in electron volts) of the dopant in the emission layer,
LUMO (host-E) indicates a LUMO energy level (expressed in electron volts) of the electron transport host in the emission layer,
HOMO(host-H) indicates a HOMO energy level (expressed in electron volts) of the hole transport host in the emission layer,
T1(dopant) indicates a triplet energy level (expressed in electron volts) of the dopant in the emission layer, and
LUMO(dopant), LUMO (host-E), and HOMO(host-H) each indicate a negative value measured by differential pulse voltammetry using ferrocene as a reference material, and
T1(dopant) indicates a value calculated from a peak wavelength of a phosphorescence spectrum of the dopant measured using a luminescence measuring device,
wherein the dopant includes a metal M and a ligand represented by Formula 1-3 and the the metal M is platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), ruthenium (Ru), rhenium (Re), beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), palladium (Pd), silver (Ag), or gold (Au):
wherein in Formula 1-3,
A 1 to A 4 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group, a substituted or unsubstituted C 1 -C 30 heterocyclic group, or a non-cyclic group,
Y 11 to Y 14 are each independently a chemical bond, O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ), and at least one of Y 11 to Y 14 are each independently O, S, N(R 91 ), B(R 91 ), P(R 91 ), or C(R 91 )(R 92 ),
T 1 to T 4 are each independently a single bond, a double bond, *—N(R 93 )—*′, *—B(R 93 )—*′, *—P(R 93 )—*′, *—C(R 93 )(R 94 )—*′, *—Si(R 93 )(R 94 )—*′, *—Ge(R 93 )(R 94 )—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O) 2 —*′, *—C(R 93 )—*′, *—C(R 93 )—*′, *—C(R 93 )═C(R 94 )—*′, *—C(═S)—*′, or *—C≡C—*′,
wherein a substituent of the substituted C 5 -C 30 carbocyclic group, a substituent of the substituted C 1 -C 30 heterocyclic group, and R 91 to R 94 are each independently hydrogen, deuterium, —F, —C 1 , —Br, —I, —SF 5 , 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 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl 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 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ), and with a proviso that the substituent of the substituted C 5 -C 30 carbocyclic group and the substituent of the substituted C 1 -C 30 heterocyclic group are not hydrogen,
Q 1 to Q 9 are each independently: —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, or —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, or a naphthyl group; or
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, or a naphthyl group, each of which is substituted with at least one of deuterium, a C 1 -C 10 alkyl group, or a phenyl group, and
*1, *2, *3, and *4 each indicate a binding site to M of the dopant.
16. The organic light-emitting device of claim 15 ,
wherein the light-emitting units comprise at least one emission layer, and charge-generation layers in a number of m-1 that are disposed between two neighboring light-emitting units selected from the light-emitting units in the number of m, wherein the charge-generation layers include an n-type charge-generation layer and a p-type charge-generation layer.
17. The organic light-emitting device of claim 1 , wherein the metal M is platinum (Pt), copper (Cu), palladium (Pd), silver (Ag), or gold (Au).
18. The organic light-emitting device of claim 1 , wherein the metal M is platinum (Pt), copper (Cu), palladium (Pd), silver (Ag), or gold (Au), and the ligand represented by Formula 1-3 comprises a benzimidazole group and a pyridine group.
19. The organic light-emitting device of claim 1 , wherein the dopant is an organometallic compound represented by Formula 1A:
wherein in Formula 1A,
M is a metal including platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), ruthenium (Ru), rhenium (Re), beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), palladium (Pd), silver (Ag), or gold (Au)
X 1 is O or S,
X 2 , X 3 , and X 4 are independently C or N, wherein at least one bond selected from a bond between X 2 and M, a bond between X 3 and M, or a bond between X 4 and M is a covalent bond, and the remaining bonds between X 2 , X 3 , or X 4 would be a coordinate bond,
Y 1 , Y 3 , Y 4 , and Y 5 are independently C or N, wherein a bond between X 2 and Y 3 , a bond between X 2 and Y 4 , a bond between Y 4 and Y 5 , a bond between Y 5 and X 51 , and a bond between X 51 and Y 3 may each be a chemical bond,
CY 1 to CY 5 are independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group, and CY 4 is not a benzimidazole group, wherein a cyclometalated ring formed by CY 5 , CY 2 , CY 3 , and M is a 6-membered ring,
X 51 is O, S, N-[(L 7 ) b7 -(R 7 ) c7 ], C(R 7 )(R 8 ), Si(R 7 )(R 8 ), Ge(R 7 )(R 8 ), C(═O), N, C(R 7 ), Si(R 7 ), or Ge(R 7 ),
wherein R 7 and R 8 are optionally linked 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,
L 1 to L 4 and L 7 are independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b1 to b4 and b7 are independently an integer from 0 to 5,
R 1 to R 4 , R 7 , and R 8 are independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryloxy group, a substituted or unsubstituted C 2 -C 60 heteroarylthio group, a substituted or unsubstituted C 3 -C 60 heteroarylalkyl 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 ), —B(Q 6 )(Q 7 ), or —P(═O)(Q 8 )(Q 9 ),
c1 to c4 are independently an integer from 1 to 5,
a1 to a4 are independently 0, 1, 2, 3, 4, or 5,
wherein
two of a plurality of neighboring groups R 1 are optionally linked 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 a plurality of neighboring groups R 2 are optionally linked 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 a plurality of neighboring groups R 3 are optionally linked 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 a plurality of neighboring groups R 4 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group, or
two or more groups selected from R 1 to R 4 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group.