Organic electroluminescence device and organometallic compound for organic electroluminescence device
An organic electroluminescence device is provided and including a first electrode, a hole transport region disposed on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the emission layer may include an organometallic compound, thereby exhibiting high luminous efficiency and long service life characteristics.
1. An organic electroluminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises an organometallic compound represented by Formula 1:
wherein, in Formula 1,
M is Pt, Pd, Ni, Au, Ag, Be, Mg, Al, Ca, Ti, Mn, Co, Zn, Ga, Zr, Ru, Rh, or Cu,
L 1 is CR 3 R 4 , NR 5 , O, SiR 6 R 7 , BR 8 , or PR 9 ,
X 1 to X 3 are each independently CR 10 or N,
ring A 1 to ring As are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 ring-forming carbon atoms,
R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n1 is an integer of 0 to 2,
n2 is an integer of 0 to 4, and
R is represented by Formula 2:
and
wherein, in Formula 2,
Ar 1 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
Ar 2 is a substituted or unsubstituted trivalent aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted trivalent heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a to R d are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or
R a and R b are bonded to each other to form a ring and/or R c and R d are bonded to each other to form a ring,
provided that, when Ar 2 is a trivalent phenyl group not substituted with any additional substituents, then R a to R d are not all methyl groups at the same time, and “—*” is the bonding position with Formula 1.
2. The organic electroluminescence device of claim 1 , wherein the emission layer is to emit phosphorescence.
3. The organic electroluminescence device of claim 1 , wherein the emission layer comprises a host and a dopant, and
the dopant comprises an organometallic compound represented by Formula 1.
4. The organic electroluminescence device of claim 1 , wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
and
wherein, in Formula 2-1 and Formula 2-2,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a′ to R d′ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, provided that, when n12 is 0, then R a′ to R d′ are not all methyl groups at the same time,
ring B 1 and ring B 2 are each independently a substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted hetero cycloalkyl having 2 to 20 carbon atoms, a substituted or unsubstituted bicycloalkyl having 4 to 20 carbon atoms, a substituted or unsubstituted hetero bicycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted tricycloalkyl having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero tricycloalkyl having 5 to 20 carbon atoms,
n11 and n13 are each independently an integer of 0 to 5, and
n12 is an integer of 0 to 3.
5. The organic electroluminescence device of claim 4 , wherein ring B 1 and ring B 2 are each independently represented by any one among Formula 3-1 to Formula 3-5:
and
wherein, in Formula 3-1 to Formula 3-5,
R a1 to R a4 , R b1 to R b5 , R c1 to R c3 , R d1 to R d6 , and R e1 to R e7 are each independently CR 31 R 32 , or NR 33 ,
R 31 to R 32 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R 33 and R c4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
at least any two groups among R a1 to R a4 , at least any two groups among R b1 to R b5 , at least any two groups among R c1 to R c3 , at least any two groups among R d1 to R d6 , or at least any two groups among R e1 to R e7 are bonded to each other to form bicycloalkyl, hetero bicycloalkyl, tricycloalkyl, or hetero tricycloalkyl, and
n21 is an integer of 0 to 4.
6. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by Formula 4:
and
wherein, in Formula 4,
R 24 and R 25 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n14 and n15 are each independently an integer of 0 to 4, and
L 1 , ring A 3 , R, R 1 , R 2 , n1, and n2 are the same as defined in Formula 1.
7. The organic electroluminescence device of claim 6 ,
wherein Formula 4 is represented by Formula 5:
and
wherein, in Formula 5,
R 26 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n16 is an integer of 0 to 3, and
L 1 , R, R 1 , R 2 , n1, n2, R 24 , R 25 , n14, and n15 are the same as defined in Formula 4.
8. An organic electroluminescence device comprising:
a first electrode;
a hole transport region on the first electrode;
an emission layer on the hole transport region;
an electron transport region on the emission layer; and
a second electrode on the electron transport region,
wherein the emission layer comprises a host and a dopant,
the dopant comprises an organometallic compound represented by Formula 1, and
the host comprises:
a first host represented by Formula 6; and
a second host represented by Formula 7:
wherein, in Formula 1,
M is Pt, Pd, Ni, Au, Ag, Be, Mg, Al, Ca, Ti, Mn, Co, Zn, Ga, Zr, Ru, Rh, or Cu,
L 1 is CR 3 R 4 , NR 5 , O, SiR 6 R 7 , BR 8 , or PR 9 ,
X 1 to X 3 are each independently CR 10 or N,
ring A 1 to ring As are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 ring-forming carbon atoms,
R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n1 is an integer of 0 to 2,
n2 is an integer of 0 to 4, and
R is represented by Formula 2:
and
wherein, in Formula 2,
Ar 1 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
Ar 2 is a substituted or unsubstituted trivalent aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted trivalent heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a to R d are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or
R a and R b are bonded to each other to form a ring and/or R c and R d are bonded to each other to form a ring, and
“—*” is the bonding position with Formula 1,
wherein, in Formula 6,
X 4 and X 6 are each independently N, or CR 44 ,
wherein, at least one among X 4 to X 6 is N,
Ar a to Ar c are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,
R 41 to R 43 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or are bonded to an adjacent group to form a ring,
R 44 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
and
wherein, in Formula 7,
Y 1 to Y 8 are each independently CR 51 or N,
X 7 is N or CR 52 ,
X 8 is a direct linkage, SiR 53 R 54 , or CR 55 R 56 ,
R 51 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or is bonded to an adjacent group to form a ring,
R 52 to R 56 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
L 2 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and/or is bonded to an adjacent group to form a ring,
Ar d is a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or is bonded to an adjacent group to form a ring, and
m is an integer of 0 to 2.
9. The organic electroluminescence device of claim 3 , wherein the emission layer further comprises a thermally activated delayed fluorescence dopant, and
the thermally activated delayed fluorescence dopant is represented by Formula 8:
and
wherein, in Formula 8,
X a to X d are each independently NR 66 , O, or S,
R 61 to R 65 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or are bonded to an adjacent group to form a ring,
R 66 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or is bonded to an adjacent group to form a ring,
n31 and n33 are each independently an integer of 0 to 3,
n32 is an integer of 0 to 2, and
n34 and n35 are each independently an integer of 0 to 4.
10. The organic electroluminescence device of claim 1 , wherein the organometallic compound represented by Formula 1 is any one among compounds represented by Compound Group 1:
11. The organic electroluminescence device of claim 8 , wherein the first host represented by Formula 6 is any one among compounds represented by Compound Group 2:
12. The organic electroluminescence device of claim 8 , wherein the second host represented by Formula 7 is any one among compounds represented by Compound Group 3:
13. The organic electroluminescence device of claim 9 , wherein the thermally activated delayed fluorescence dopant represented by Formula 8 is any one among compounds represented by Compound Group 4:
14. An organometallic compound represented by Formula 1:
and
wherein, in Formula 1,
M is Pt, Pd, Ni, Au, Ag, Be, Mg, Al, Ca, Ti, Mn, Co, Zn, Ga, Zr, Ru, Rh, or Cu,
L 1 is CR 3 R 4 , NR 5 , O, SiR 6 R 7 , BR 8 , or PR 9 ,
X 1 to X 3 are each independently CR 10 or N,
ring A 1 to ring A 3 are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 ring-forming carbon atoms,
R 1 to R 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n1 is an integer of 0 to 2,
n2 is an integer of 0 to 4, and
R is represented by Formula 2-below:
and
wherein, in Formula 2,
Ar 1 and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
Ar 2 is a substituted or unsubstituted trivalent aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted trivalent heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a to R d are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or
R a and R b are bonded to each other to form a ring and/or R c and R d are bonded to each other to form a ring,
provided that, when Ar 2 is a trivalent phenyl group not substituted with any additional substituents, then Ra to Ra are not all methyl groups at the same time, and “—*” is the bonding position with Formula 1.
15. The organometallic compound of claim 14 , wherein Formula 2 is represented by Formula 2-1 or Formula 2-2:
and
wherein, in Formula 2-1 and Formula 2-2,
R 21 to R 23 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R a′ to R d′ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, provided that, when n12 is 0, then R a′ to R d′ are not all methyl groups at the same time,
ring B 1 and ring B 2 are each independently a substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted hetero cycloalkyl having 2 to 20 carbon atoms, a substituted or unsubstituted bicycloalkyl having 4 to 20 carbon atoms, a substituted or unsubstituted hetero bicycloalkyl having 3 to 20 carbon atoms, a substituted or unsubstituted tricycloalkyl having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero tricycloalkyl having 5 to 20 carbon atoms,
n11 and n13 are each independently an integer of 0 to 5, and
n12 is an integer of 0 to 3.
16. The organometallic compound of claim 15 , wherein ring B 1 and ring B 2 are each independently represented by any one among Formula 3-1 to Formula 3-5:
and
wherein, in Formula 3-1 to Formula 3-5,
R a1 to R a4 , R b1 to R b5 , R c1 to R c3 , R d1 to R d6 , and R e1 to R e7 are each independently CR 31 R 32 , or NR 33 ,
R 31 to R 32 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
R 33 and R c4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
at least any two groups among R a1 to R a4 , at least any two groups among R b1 to R b5 , at least any two groups among R c1 to R c3 , at least any two groups among R d1 to R d6 , or at least any two groups among R e1 to R e7 are bonded to each other to form bicycloalkyl, hetero bicycloalkyl, tricycloalkyl, or hetero tricycloalkyl, and
n21 is an integer of 0 to 4.
17. The organometallic compound of claim 15 , wherein R a ′ to R d ′ are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, and
ring B 1 and ring B 2 are each independently a substituted or unsubstituted cyclopentane, a substituted or unsubstituted cyclohexane, a substituted or unsubstituted hexahydropyrimidine, a substituted or unsubstituted cycloheptane, a substituted or unsubstituted tetraline, a substituted or unsubstituted bicyclo[3.3.1]nonyl, or a substituted or unsubstituted tricyclo[3.3.1.13.7]decane.
18. The organometallic compound of claim 14 , wherein Formula 1-above is represented by Formula 4:
and
wherein, in Formula 4,
R 24 and R 25 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n14 and n15 are each independently an integer of 0 to 4, and
L 1 , ring A 3 , R, R 1 , R 2 , n1, and n2 are the same as defined in Formula 1.
19. The organometallic compound of claim 18 , wherein Formula 4 is represented by Formula 5:
and
wherein, in Formula 5 above,
R 26 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
n16 is an integer of 0 to 3, and
L 1 , R, R 1 , R 2 , n1, n2, R 24 , R 25 , n14, and n15 are the same as defined in Formula 4.
20. The organometallic compound of claim 14 , wherein the organometallic compound represented by Formula 1 is any one among compounds represented by Compound Group 1: