Light emitting device and amine compound for light emitting device
A light emitting device includes a first electrode, a second electrode facing the first electrode, and organic layers disposed between the first electrode and the second electrode, wherein the organic layers include at least one organic layer that includes an amine compound represented by Formula 1. The light emitting device may exhibit improved luminous efficiency characteristics.
1 . A light emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers disposed between the first electrode and the second electrode, wherein
the plurality of organic layers comprises at least one organic layer that includes an amine compound represented by Formula 1:
wherein in Formula 1,
L is 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,
Ar 1 and Ar 2 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,
m is 1 or 2,
M is a group represented by Formula 2, and
at least one of Ar 1 and Ar 2 is a group represented by Formula 3:
wherein in Formula 2,
one of R a , R b , and R c is a position linked to L in Formula 1,
the remainder of R a to R h 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, and
at least one of the remainder of R a to R h is not a hydrogen atom:
wherein in Formula 3,
R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
where the case in which each of R 1 and R 2 is an unsubstituted phenyl group is excluded,
is a position linked to N in Formula 1,
n 1 to n 3 are each independently an integer from 0 to 4,
n 4 is an integer from 0 to 5, and
wherein at least one arene moiety in Formula 3 is bound to two other arene moieties of Formula 3 at ortho or meta positions, and
when L in Formula 1 is a p-phenylene group, when a group represented by Formula 3 is a group represented by Formula 3-a, and when R a in Formula 2 is linked to L in Formula 1,
R b in Formula 2 is not an unsubstituted phenyl group:
and
when R a in Formula 2 is linked to L in Formula 1, R b and R h in Formula 2 are each independently a hydrogen atom, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
2 . The light emitting device of claim 1 , wherein
the plurality of organic layers comprise:
a hole transport region disposed on the first electrode;
an emission layer disposed on the hole transport region; and
an electron transport region disposed on the emission layer, and
the hole transport region comprises the amine compound.
3 . The light emitting device of claim 2 , wherein
the hole transport region further comprises:
a hole injection layer disposed on the first electrode; and
a hole transport layer disposed on the hole injection layer, and
the hole transport layer comprises the amine compound.
4 . The light emitting device of claim 2 , wherein
the hole transport region comprises a plurality of hole transport organic layers, and
the plurality of hole transport organic layers comprises a layer that is adjacent to the emission layer and includes the amine compound.
5 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is a monoamine compound.
6 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 4-1 or Formula 4-2:
wherein in Formula 4-1 and Formula 4-2,
Ar 1 , Ar 2 , L, R a to R h , and m are the same as defined in Formula 1 and Formula 2.
7 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is represented by one of Formula 5-1 to Formula 5-3:
wherein in Formula 5-1 to Formula 5-3,
X 1 is N(R 10 ), O, or S,
R 5 to R 10 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,
n 5 to n 9 are each independently an integer from 0 to 4,
the sum of n 8 and n 9 is equal to or less than 6, and
M, Ar 1 , and Ar 2 are the same as defined in Formula 1.
8 . The light emitting device of claim 7 , wherein the amine compound represented by Formula 1 is represented by one of Formula 6-1 to Formula 6-5:
wherein in Formula 6-1 to Formula 6-5,
n 8-1 is an integer from 0 to 2,
Ar 1 , Ar 2 , M, X 1 , R 5 to R 9 , n 5 to n 7 , and n 9 are the same as defined in Formula 1 and Formula 5-1 to Formula 5-3.
9 . The light emitting device of claim 1 , wherein
Ar 1 is a group represented by Formula 3, and
Ar 2 is a group represented by one of Formula 7-1 to Formula 7-5:
wherein in Formula 7-1 to Formula 7-5,
Y 1 is N(R 11 ), O, or S,
R a1 to R a6 and R 11 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,
R a7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon group, a substituted or unsubstituted alkenyl group having 2 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 is bonded to an adjacent group to form a ring,
n 10 is an integer from 0 to 5,
n 11 and n 16 are each independently an integer from 0 to 7,
n 12 is an integer from 0 to 9,
n 13 is an integer from 0 to 3,
n 14 and n 15 are each independently an integer from 0 to 4, and
is a position linked to N in Formula 1.
10 . The light emitting device of claim 1 , wherein the remainder of R a to R h are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group, provided that at least one of the remainder of R a to R h is not a hydrogen atom.
11 . The light emitting device of claim 1 , wherein the at least one of Ar 1 and Ar 2 that is represented by Formula 3 is a group represented by one of Formula 8-1 to Formula 8-9:
wherein in Formula 8-1 to Formula 8-9,
R 1 to R 4 , n 1 to n 4 , and are the same as defined in Formula 3.
12 . The light emitting device of claim 1 , wherein R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
13 . The light emitting device of claim 1 , wherein
when L in Formula 1 is linked to R a in Formula 2, at least one of R b to R h is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group, and
when L in Formula 1 above is linked to R b in Formula 2, at least one of R a and Re to R h is a substituted or unsubstituted phenyl group.
14 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 comprises at least one selected from Compound Group 1:
15 . An amine compound represented by Formula 1:
wherein in Formula 1,
L is 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,
Ar 1 and Ar 2 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,
m is 1 or 2,
M is a group represented by Formula 2, and
at least one of Ar 1 and Ar 2 is a group represented by Formula 3:
wherein in Formula 2,
one of R a , R b , and R c is a position linked to L in Formula 1,
the remainder of R a to R h 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, and
at least one of the remainder of R a to R h is not a hydrogen atom:
wherein in Formula 3,
R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
where the case in which each of R 1 and R 2 is an unsubstituted phenyl group is excluded,
is a position linked to N in Formula 1,
n 1 to n 3 are each independently an integer from 0 to 4,
n 4 is an integer from 0 to 5,
wherein at least one arene moiety in Formula 3 is bound to two other arene moieties of Formula 3 at ortho or meta positions, and
when L in Formula 1 is a p-phenylene group, when a group represented by Formula 3 is a group represented by Formula 3-a, and when R a in Formula 2 is linked to L in Formula 1,
R b in Formula 2 is not an unsubstituted phenyl group:
and
when R a in Formula 2 is linked to L in Formula 1, R b and R h in Formula 2 are each independently a hydrogen atom, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
16 . The amine compound of claim 15 , wherein the amine compound represented by Formula 1 is represented by Formula 4-1 or Formula 4-2:
wherein in Formula 4-1 and Formula 4-2,
Ar 1 , Ar 2 , L, R a to R h , and m are the same as defined in Formula 1 and Formula 2.
17 . The amine compound of claim 15 , wherein the amine compound represented by Formula 1 is represented by one of Formula 5-1 to Formula 5-3:
wherein in Formula 5-1 to Formula 5-3,
X 1 is N(R 10 ), O, or S,
R 5 to R 10 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,
n 5 to n 9 are each independently an integer from 0 to 4,
the sum of n 8 and n 9 is equal to or less than 6, and
M, Ar 1 , and Ar 2 are the same as defined in Formula 1.
18 . The amine compound of claim 17 , wherein the amine compound represented by Formula 1 is represented by one of Formula 6-1 to Formula 6-5:
wherein in Formula 6-1 to Formula 6-5,
n 8-1 is an integer from 0 to 2,
Ar 1 , Ar 2 , M, X 1 , R 5 to R 9 , n 5 to n 7 , and n 9 are the same as defined in Formula 1 and Formula 5-1 to Formula 5-3.
19 . The amine compound of claim 15 , wherein
Ar 1 is a group represented by Formula 3, and
Ar 2 is a group represented by one of Formula 7-1 to Formula 7-5:
wherein in Formula 7-1 to Formula 7-5,
Y 1 is N(R 11 ), O, or S,
R a1 to R a6 and R 11 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,
R a7 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon group, a substituted or unsubstituted alkenyl group having 2 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 is bonded to an adjacent group to form a ring,
n 10 is an integer from 0 to 5,
n 11 and n 16 are each independently an integer from 0 to 7,
n 12 is an integer from 0 to 9,
n 13 is an integer from 0 to 3,
n 14 and n 15 are each independently an integer from 0 to 4, and
is a position linked to N in Formula 1.
20 . The amine compound of claim 15 , wherein the amine compound represented by Formula 1 is one selected from Compound Group 1:
21 . A display apparatus comprising:
a light emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers disposed between the first electrode and the second electrode, wherein
the plurality of organic layers comprises at least one organic layer that includes an amine compound represented by Formula 1:
wherein in Formula 1,
L is 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,
Ar 1 and Ar 2 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,
m is 1 or 2,
M is a group represented by Formula 2, and
at least one of Ar 1 and Ar 2 is a group represented by Formula 3:
wherein in Formula 2,
one of R a , R b , and R c is a position linked to L in Formula 1,
the remainder of R a to R h 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, and
at least one of the remainder of R a to R h is not a hydrogen atom:
wherein in Formula 3,
R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,
where the case in which each of R 1 and R 2 is an unsubstituted phenyl group is excluded,
is a position linked to N in Formula 1,
n 1 to n 3 are each independently an integer from 0 to 4,
n 4 is an integer from 0 to 5, and
wherein at least one arene moiety in Formula 3 is bound to two other arene moieties of Formula 3 at ortho or meta positions, and
when L in Formula 1 is a p-phenylene group, when a group represented by Formula 3 is a group represented by Formula 3-a, and when R a in Formula 2 is linked to L in Formula 1, R b in Formula 2 is not an unsubstituted phenyl group:
[Formula 3-a]
when R a in Formula 2 is linked to L in Formula 1, R b and R h in Formula 2 are each independently a hydrogen atom, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.