Light emitting device and organometallic compound for light emitting device
A light emitting device of an embodiment includes 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 includes an organometallic compound represented by Formula 1, thereby showing long life and high efficiency.
1 . A light emitting device, comprising:
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 comprises an organometallic compound represented by Formula 1:
wherein in Formula 1,
M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os,
rings A1, A2, and A3 are each independently a substituted or unsubstituted hydrocarbon ring group of 5 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group of 1 to 60 ring-forming carbon atoms,
L 1 and L 3 are each independently a direct linkage, *—O—*′, *—S—*′, *—C(R a1 )(R a2 )—*′, *—C(R a3 )=*′, *=C(R a4 )—*′, *—C(R a5 )═C(R a6 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R a7 )—*′, *—N(R a8 )—*′, *—P(R a9 )—*′, *—Si(R a10 )(R a11 )*′, *—P(R a12 )(R a13 )—*′, or *—Ge(R a14 )(R a15 )—*′, where * and *′ are each a bonding site,
R 1 , and Ral to R a15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
n1 and n3 are each independently 0 or 1, and
ring A4 is a group represented by one of Formula 2-1 to Formula 2-3:
wherein in Formula 2-1 to Formula 2-3,
is a bonding site,
L 2 is a direct linkage, *—O*′, *—S—*′, *—C(R a1′ )(R a2′ )—*′, *—C(R a3′ )=*′, *=C(R a4′ )—*′, *—C(R a5′ )═C(R a6′ )*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R a7′ )—*′, *—N(R a8′ )*′, *—P(R a9′ )—*′, * Si(R a10′ )(R a11′ )—*′, *—P(R a12′ )(R a13′ )—*′, or *—Ge(R a14′ )(R a15′ )*′, where * and *′ are each a bonding site,
R 2 , and R a1′ to R a15′ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
a is an integer from 0 to 2, and
n2 is 0 or 1.
2 . The light emitting device of claim 1 , wherein the emission layer emits phosphorescence.
3 . The light emitting device of claim 1 , wherein
the emission layer comprises a host and a dopant, and
the dopant comprises the organometallic compound represented by Formula 1.
4 . The light emitting device of claim 1 , wherein
the emission layer comprises a host, a dopant, and a sensitizer, and
the sensitizer comprises the organometallic compound represented by Formula 1.
5 . The light emitting device of claim 1 , wherein ring A2 is a group represented by one of Formula A-1 to Formula A-3:
wherein in Formula A-1 to Formula A-3,
is a bonding site,
R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
d is an integer from 0 to 3, and
d′ is an integer from 0 to 2.
6 . The light emitting device of claim 1 , wherein ring A3 is a group represented by one of Formula B-1 to Formula B-4:
wherein in Formula B-1 to Formula B-4,
is a bonding site,
R 4 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
c is an integer from 0 to 4.
7 . The light emitting device of claim 1 , wherein the organometallic compound represented by Formula 1 is represented by Formula 3:
wherein in Formula 3,
X 1 to X 3 are each independently N or C(R b ),
wherein one of X 1 or X 2 is N,
R 3 to R 6 and R b are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
b and c are each independently an integer from 0 to 4, and
M, ring A4, L 1 , L 3 , n1, n3, and R 1 are the same as defined in Formula 1.
8 . The light emitting device of claim 7 , wherein the organometallic compound represented by Formula 3 is represented by Formula 4:
wherein in Formula 4,
M, ring A4, L 1 , L 3 , n1, n3, b, c, R 1 , R 3 to R 6 , and R b are the same as defined in Formula 3.
9 . The light emitting device of claim 8 , wherein
R 5 and R 6 are each a hydrogen atom, and
R b is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms.
10 . The light emitting device of claim 7 , wherein the organometallic compound represented by Formula 3 is represented by Formula 5:
wherein in Formula 5,
M, ring A4, L 1 , L 3 , n1, n3, b, c, R 1 , R 3 to R 6 are the same as defined in Formula 3.
11 . The light emitting device of claim 7 , wherein the organometallic compound represented by Formula 3 is represented by Formula 6:
wherein in Formula 6,
R 4 is a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
M, ring A4, L 1 , L 3 , n1, n3, b, X 3 , R 1 , R 3 , R 5 , and R 6 are the same as defined in Formula 3.
12 . The light emitting device of claim 7 , wherein the organometallic compound represented by Formula 3 is represented by one of Formula 7-1 to Formula 7-3:
wherein in Formula 7-1 to Formula 7-3,
L 2 is a direct linkage, *—O—*′, or *—C(R a1′ )(R a2′ )—*′, where * and *′ are each a bonding site,
R 2 , R a1′ , and R a2′ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
a is an integer from 0 to 2, and
M, L 1 , L 3 , n1, n3, b, c, Ri, and R 3 to R 6 are the same as defined in Formula 3.
13 . The light emitting device of claim 1 , wherein the organometallic compound represented by Formula 1 is at least one selected from Compound Group 1:
14 . An organometallic compound represented by Formula 1:
wherein in Formula 1,
M is Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os,
rings A1, A2, and A3 are each independently a substituted or unsubstituted hydrocarbon ring group of 5 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group of 1 to 60 ring-forming carbon atoms,
L 1 and L 3 are each independently a direct linkage, *—O—*′, *—S—*′, *—C(R a1 )(R a2 )—*′, *—C(R a3 )=*′, *=C(R a4 )—*′, *—C(R a8 )═C(R a6 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R a7 )—*′, *—N(R a8 )—*′, *—P(R a9 )—*′, *—Si(R a10 )(R a1 )*′, *—P(R a12 )(R a13 )—*′, or *—Ge(R a14 )(R a1 )—*′, where * and *′ are each a bonding site,
R 1 , and Ral to R a15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
n1 and n3 are each independently 0 or 1, and
ring A4 is a group represented by one of Formula 2-1 to Formula 2-3:
wherein in Formula 2-1 to Formula 2-3,
is a bonding site,
L 2 is a direct linkage, *—O*′, *—S—*′, *—C(R a1′ )(R a2′ )—*′, *—C(R a3′ )=*′, *=C(R a4′ )—*′, *—C(R a5′ )═C(R a6′ )*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R a7′ )—*′, *—N(R a5′ )*′, *—P(R a9′ )—*′, * Si(R a10′ )(R a11′ )—*′, *—P(R a12′ )(R a13′ )-*′ or *—Ge(R a14′ )(R a15′ )—*′, where * and *′ are each a bonding site,
R 2 , and R a1′ to R a15′ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
a is an integer from 0 to 2, and
n2 is 0 or 1.
15 . The organometallic compound of claim 14 , wherein ring A2 is a group represented by one of Formula A-1 to Formula A-3:
wherein in Formula A-1 to Formula A-3,
is a bonding site,
R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
d is an integer from 0 to 3, and
d′ is an integer from 0 to 2.
16 . The organometallic compound of claim 14 , wherein ring A3 is a group represented by one of Formula B-1 to Formula B-4:
wherein in Formula B-1 to Formula B-4,
is a bonding site,
R 4 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and
c is an integer of 0 to 4.
17 . The organometallic compound of claim 14 , wherein the organometallic compound represented by Formula 1 is represented by Formula 3:
wherein in Formula 3,
X 1 to X 3 are each independently N or C(R b ),
wherein one of X 1 or X 2 is N,
R 3 to R 6 and R b are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
b and c are each independently an integer from 0 to 4, and
M, ring A4, L 1 , L 3 , n1, n3, and Ri are the same as defined in Formula 1.
18 . The organometallic compound of claim 17 , wherein the organometallic compound represented by Formula 3 is represented by Formula 4:
wherein in Formula 4,
M, ring A4, L 1 , L 3 , n1, n3, b, c, R 1 , R 3 to R 6 , and R b are the same as defined in Formula 3.
19 . The organometallic compound of claim 17 , wherein the organometallic compound represented by Formula 3 is represented by Formula 5:
wherein in Formula 5,
M, ring A4, L 1 , L 3 , n1, n3, b, c, R 1 , and R 3 to R 6 are the same as defined in Formula 3.
20 . The organometallic compound of claim 14 , wherein the organometallic compound represented by Formula 1 is at least one selected from Compound Group 1: