Light emitting device and amine compound for the same
A light emitting device, includes: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode and including an amine compound of Formula 1: in Formula 1, the variables are described herein.
1 . A light emitting device, comprising:
a first electrode;
a second electrode disposed on the first electrode; and
at least one functional layer disposed between the first electrode and the second electrode and comprising an amine compound of Formula 1:
in Formula 1,
R is a hydrogen atom or a deuterium atom,
a1 and a2 are each, independently from one another, an integer of 0 to 4,
R 1 and R 2 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms,
a3 is an integer of 0 to 2,
a4 is an integer of 0 to 3,
R 3 and R 4 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms,
with the proviso that R 1 to R 4 , Ar 1 and Ar 2 do not comprise an amine group as a substituent,
with the proviso that the amine compound does not comprise a substituted or unsubstituted thiophenyl group, and
with the proviso that the thiophenyl group is not fused to another ring.
2 . The light emitting device of claim 1 , wherein Formula 1 is of Formula 2-1:
in Formula 2-1,
a11 is an integer of 0 to 4,
Ar 11 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
R 11 to R 15 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, or combined with an adjacent group to form a ring,
Ar 13 is a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, and
a1 to a4, R, and R 1 to R 4 have, independently from one another, the same meaning as defined in Formula 1.
3 . The light emitting device of claim 1 , wherein Formula 1 is of Formula 2-2:
in Formula 2-2,
n0 is an integer of 0 to 3,
L 0 is a direct linkage, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms,
W 1 is CR 18 R 19 , NR 20 , O, or S,
a16 and a17 are each, independently from one another, an integer of 0 to 4,
R 16 to R 20 are each, independently from one another, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, or combined with an adjacent group to form a ring,
Ar 13 is a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, and
a1 to a4, R, and R 1 to R 4 have, independently from one another, the same meaning as defined in Formula 1.
4 . The light emitting device of claim 1 , wherein Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted carbazole group, an unsubstituted naphthobenzofuran group, or an unsubstituted benzonaphthothiophene group.
5 . The light emitting device of claim 1 , wherein Ar 1 and Ar 2 are each, independently from one another, one of A-1 to A-7:
a21 is an integer of 0 to 5,
in A-2,
a22 is an integer of 0 to 7, and
R 22 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
in A-3,
a23 is an integer of 0 to 9,
in A-4,
a24 is an integer of 0 to 3, and
a25 and a26 are each, independently from one another, an integer of 0 to 4,
in A-5,
n1 is 0 or 1,
L 1 is a direct linkage,
a27 is an integer of 0 to 7, and
a28 is an integer of 0 to 10,
in A-6,
X 1 is NR 30 , O, or S, and
a29 is an integer of 0 to 7,
in A-7,
X 2 is O, or S, and
a31 is an integer of 0 to 9, and
in A-1, and A-3 to A-7,
R 21 , and R 23 to R 31 are each, independently from one another, a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms.
6 . The light emitting device of claim 1 , wherein at least one of Ar 1 and Ar 2 is a substituted or unsubstituted phenyl group.
7 . The light emitting device of claim 1 , wherein R 1 and R 2 are each, independently from one another, a deuterium atom, a fluorine atom, a methyl group, or a t-butyl group.
8 . The light emitting device of claim 1 , wherein at least one of R 1 to R 4 is a deuterium atom, or at least one of R 1 to R 4 , Ar 1 and Ar 2 comprises a deuterium atom as a substituent.
9 . The light emitting device of claim 1 , wherein the at least one functional layer comprises an emission layer, 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, and
the hole transport region comprises the amine compound.
10 . The light emitting device of claim 9 , wherein the hole transport region comprises a hole injection layer disposed on the first electrode, a hole transport layer disposed on the hole injection layer, and an electron blocking layer disposed on the hole transport layer, and
at least one of the hole injection layer, the hole transport layer, and the electron blocking layer comprises the amine compound.
11 . The light emitting device of claim 10 , wherein the electron blocking layer comprises the amine compound, and the hole transport layer comprises a compound of Formula H-1:
in Formula H-1,
b1 and b2 are each, independently from one another, an integer of 0 to 10,
L 2 and L 3 are each, independently from one another, a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms, and
Ar 21 to Ar 23 are each, independently from one another, 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.
12 . The light emitting device of claim 1 , wherein the amine compound comprises one compound of Compound Group 1:
13 . An amine compound of Formula 1:
in Formula 1,
R is a hydrogen atom or a deuterium atom,
a1 and a2 are each, independently from one another, an integer of 0 to 4,
R 1 and R 2 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms,
a3 is an integer of 0 to 2,
a4 is an integer of 0 to 3,
R 3 and R 4 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms,
with the proviso that R 1 to R 4 , Ar 1 and Ar 2 do not comprise an amine group as a substituent,
with the proviso that the amine compound does not comprise a substituted or unsubstituted thiophenyl group, and
with the proviso that the thiophenyl group is not fused to another ring.
14 . The amine compound of claim 13 , wherein Formula 1 is of Formula 2-1:
in Formula 2-1,
a11 is an integer of 0 to 4,
Ar 11 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
R 11 to R 15 are each, independently from one another, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, or combined with an adjacent group to form a ring,
Ar 3 is a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, and
a1 to a4, R, and R 1 to R 4 have, independently from one another, the same meaning as defined in Formula 1.
15 . The amine compound of claim 4 , wherein Formula 1 is of Formula 2-2:
in Formula 2-2,
n0 is an integer of 0 to 3,
L 0 is a direct linkage, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms,
W 1 is CR 18 R 19 , NR 20 , O, or S,
a16 and a17 are each, independently from one another, an integer of 0 to 4,
R 16 to R 20 are each, independently from one another, a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkenyl group of 2 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, or combined with an adjacent group to form a ring,
Ar 13 is a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms, and
a1 to A4, R, and R 1 to R 4 have, independently from one another, the same meaning as defined in Formula 1.
16 . The amine compound of claim 13 , wherein Ar 1 and Ar 2 are each, independently from one another, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted carbazole group, an unsubstituted naphthobenzofuran group, or an unsubstituted benzonaphthothiophene group.
17 . The amine compound of claim 13 , wherein Ar 1 and Ar 2 are each, independently from one another, one of A-1 to A-7:
in A-1,
a21 is an integer of 0 to 5,
in A-2,
a22 is an integer of 0 to 7, and
R 22 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms,
in A-3,
a23 is an integer of 0 to 9,
in A-4,
a24 is an integer of 0 to 3, and
a25 and a26 are each, independently from one another, an integer of 0 to 4,
in A-5,
n1 is 0 or 1,
L 1 is a direct linkage,
a27 is an integer of 0 to 7, and
a28 is an integer of 0 to 10,
in A-6,
X 1 is NR 30 , O, or S, and
a29 is an integer of 0 to 7,
in A-7,
X 2 is O, or S, and
a31 is an integer of 0 to 9, and
in A-1, and A-3 to A-7,
R 21 , and R 23 to R 31 are each, independently from one another, a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group of 6 to 40 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 40 ring-forming carbon atoms.
18 . The amine compound of claim 13 , wherein at least one of Ar 1 and Ar 2 is a substituted or unsubstituted phenyl group.
19 . The amine compound of claim 13 , wherein R 1 and R 2 are each, independently from one another, a deuterium atom, a fluorine atom, a methyl group, or a t-butyl group.
20 . The amine compound of claim 13 , wherein at least one of R 1 to R 4 is a deuterium atom, or at least one of R 1 to R 4 , Ar 1 and Ar 2 comprises a deuterium atom as a substituent.
21 . The amine compound of claim 13 , wherein Formula 1 is one compound of Compound Group 1: