Amine compound and organic light-emitting diode including same
The present invention relates to a novel amine compound and an organic light-emitting diode including the same. More particularly, the present disclosure relates to an amine compound that allows for high efficiency and a long lifespan in an organic light-emitting diode if used as an element therein and to an organic light-emitting diode including the same.
1. An amine compound represented by the following Chemical Formula A-1:
wherein,
A 3 and A 4 , which are the same or different, are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms;
two adjacent carbon atoms within the aromatic ring of A 3 are linked to M 1 and M 2 , respectively, in order to form a 5-membered, fused ring;
two adjacent carbon atoms within the aromatic ring of A 4 are linked to M 3 and M 4 , respectively, in order to form a 5-membered, fused ring;
linkers L 1 to L 6 , which are the same or different, are each independently selected from among a single bond and a substituted or unsubstituted arylene of 6 to 60 carbon atoms;
at least one of the aromatic rings of A 3 to A 4 has one substituent selected from among a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, and a halogen selected from F, Cl, Br, and I;
M 1 to M 4 , which are the same or different, are each independently a single bond, O, S, or CR 3 R 4 , with a proviso that one of M 1 and M 2 is a single bond, and one of M 3 and M 4 is a single bond;
substituents R 1 to R 4 and Ar 1 to Ar 4 , which are the same or different, are each independently selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, a nitro, and a halogen;
in the alterative for R 1 and R 2 , R 1 and R 2 are connected to each other to form a mono- or polycyclic aliphatic or aromatic ring which may bear at least one heteroatom selected from among N, O, P, Si, and S as a ring member;
p1 and p2, r1 and r2, and s1 and s2 are each independently an integer of 1 to 3 and when any of them is 2 or greater, the corresponding linkers L 1 to L 6 are the same or different;
x is an integer of 1;
y is an integer of 1;
in the alternative for Ar 1 and Ar 4 , Ar 1 and Ar 2 are connected to each other to form a ring and/or Ar 3 and Ar 4 are connected to each other to form a ring;;
substituents R's which are the same or different, are each independently selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a cyano, a nitro, and a halogen;
Chemical Formula A-1 excludes compounds in which A 3 and A 4 each have one phenyl group and R 1 and R 2 form a ring with each other; and
the term “substituted” in the expression “substituted or unsubstituted” used for Chemical Formula A means having at least one substituent selected from the group consisting of a deuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 6 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, and an arylsilyl of 6 to 24 carbon atoms.
2. The amine compound of claim 1 , wherein the substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms in A 2 and A 4 , which are the same or different, are each independently one selected from among [Structural Formula 10] to [Structural Formula 21]:
wherein,
“_*” denotes a bonding site linked to M 1 to M 4 to form a fuse ring; and
R is as defined for R 1 and R 2 , and m is an integer of 1 to 8 wherein when m is 2 or greater or when R exists as multiple radicals, the resulting R's may be the same or different.
3. The amine compound of claim 1 , wherein the linkers L 1 to L 6 are each a single bond or a substituted or unsubstituted arylene of 6 to 20 carbon atoms.
4. The amine compound of claim 3 , wherein the linkers L 1 to L 6 are each a single bond or one selected from among the following [Structural Formula 22], [Structural Formula 23], [Structural Formula 25], [Structural Formula 27], [Structural Formula 28], and [Structural Formula 30], p1 and p2, r1 and r2, and s1 and s2 are each 1 or 2, and x is 1:
wherein, each of unsubstituted carbon atoms of the aromatic ring moiety may be bound with a hydrogen atom or a deuterium atom.
5. The amine compound of claim 1 , wherein the substituents R 1 to R 4 , and Ar 1 to Ar 4 , which are the same or different, are each independently one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl of 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl of 2 to 20 carbon atoms bearing at least one selected from among O, N,
S, and Si as a heteroatom, a cyano, and a halogen.
6. The amine compound of claim 1 , wherein the amine compound is one selected from among the compounds represented by [Chemical Formula 1] to [Chemical Formula 15], [Chemical Formula 17], [Chemical Formula 19] to [Chemical Formula 30],
[Chemical Formula 32], [Chemical Formula 34] to [Chemical Formula 47], and [Chemical Formula 49] to [Chemical Formula 51]:
7. An organic light-emitting diode, comprising a first electrode; a second electrode facing the first electrode, and a light-emitting layer interposed between the first electrode and the second electrode, wherein the light-emitting layer comprises at least one of the amine compounds of claim 1 .
8. The organic light-emitting diode of claim 7 , further comprising at least one selected from among a hole injection layer, a hole transport layer, a functional layer capable of both hole injection and hole transport, an electron transport layer, and an electron injection layer, in addition to the light-emitting layer.
9. The organic light-emitting diode of claim 7 , wherein the light emitting layer includes a host and a dopant wherein the amine compound represented by Chemical Formula A is used as the dopant.
10. The organic light-emitting diode of claim 8 , wherein at least one of the layers is formed using a deposition process or a solution process.
11. The organic light-emitting diode of claim 7 , wherein the organic light-emitting diode is used for a device selected from among a flat display device, a flexible display device, a monochrome or grayscale flat illumination device, and a monochrome or grayscale flexible illumination device.