Organic light-emitting diode with high efficiency and long lifetime

1. An organic light-emitting diode, comprising:

a first electrode;

a second electrode facing the first electrode; and

an emissive layer intercalated between the first electrode and the second electrode, wherein the emissive layer comprises at least one of the amine compounds represented by the following Chemical Formula A, and emits light with a color coordinate CIEy on a chromaticity diagram of 0.1 or less:

wherein Q 1 is

Q 2 is

A 1 , A 2 , E, and F may be the same or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 40 carbon atoms wherein two adjacent carbon atoms of the aromatic ring A 1 and two adjacent carbon atoms of the aromatic ring A 2 form a 5-membered fused ring together with a carbon atom to which substitutents R 1 and R 2 are bonded;

linkers L 1 to L 12 may be the same or different, and are each independently selected from among a direct bond, a substituted or unsubstituted alkylene of 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene of 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene of 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene of 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene of 2 to 60 carbon atoms, a substituted or unsubstituted arylene of 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene of 2 to 60 carbon atoms;

M is any one selected from among N—R 3 , CR 4 R 5 , SiR 6 R 7 , GeR 8 R 9 , O, S, and Se;

R 1 to R 9 , and Ar 1 to Ar 8 may be the same or different, and are each independently any one selected from among hydrogen, deuterium, 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 alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium of 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium of 6 to 30 carbon atoms, a cyano, a nitro, and a halogen, with a proviso that R 1 and R 2 together may form a mono- or polycyclic aliphatic or aromatic ring that may be a heterocyclic ring with a heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te as a ring member;

p1 to p4, r1 to r4, and s1 to s4 are each independently an integer of 1 to 3, with a proviso that when any of them is 2 or greater, the corresponding linkers may be the same or different,

x is an integer of 1 or 2, and y and z may be the same or different and are each independently an integer of 0 to 3; and

Ar 1 may form a ring with Ar 2 , Ar 3 may form a ring with Ar 4 , Ar 5 may form a ring with Ar 6 , and Ar 7 may form a ring with Ar 8 ,

two adjacent carbon atoms of the A1 ring occupy respective positions * of Q 2 to form a fused ring, and two adjacent carbon atoms of the A 2 ring occuply respective positions * of Q 1 to form a fused ring,

the term ‘substituted’ in the expression ‘substituted or unsubstituted’ is to have a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl of 1 to 24 carbon atoms, halogenated alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, arylalkyl of 7 to 24 carbon atoms, heteroaryl of 2 to 24 carbon atoms or heteroarylalkyl of 2 to 24 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkylamino of 1 to 24 carbon atoms, arylamino of 6 to 24 carbon atoms, hetero arylamino of 1 to 24 carbon atoms, alkylsilyl of 1 to 24 carbon atoms, arylsilyl of 6 to 24 carbon atoms, and aryloxy of 6 to 24 carbon atoms.

2. The organic light-emitting diode of claim 1 , wherein the emissive layer comprises a host and a dopant, and the amine compound of Chemical Formula A serves as the dopant.

3. The organic light-emitting diode of claim 2 , wherein the emissive layer includes as a host an anthracene derivative represented by the following Chemical Formula B:

wherein R 11 to R 18 may be the same or different, and are the same as above defined for R 1 to R 9 ;

Ar 9 , and Ar 10 may be the same or different and are each independently any one selected from among hydrogen, deuterium, 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 alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms;

L 13 represents a direct bond, or is a substituted or unsubstituted arylene of 6 to 20 carbon atoms or a substituted or unsubstituted heteroarylene of 2 to 20 carbon atoms; and

k is an integer of 1 to 3, with a proviso that when k is 2 or greater, the corresponding linkers L13 may be the same or different.

4. The organic light-emitting diode of claim 3 , wherein the substituent Arg of Chemical Formula B is represented by the following Chemical Formula C-1:

wherein, R 21 to R 25 may be the same or different and are each the same as above defined for R 1 to R 9 , and

an adjacent two of them may be bonded to each other to form a saturate or unsaturated ring.

5. The organic light-emitting diode of claim 4 , wherein L13 represents a direct bond or a substituted or unsubstituted arylene of 6 to 20 carbon atoms, and

k is an integer of 1 to 2, with a proviso that when k is 2, the corresponding linkers L13 may be the same or different.

6. The organic light-emitting diode of claim 3 , wherein the anthracene derivative is one selected from among compounds represented by the following Chemical Formula 22 to Chemical Formula 60:

7. The organic light-emitting diode of claim 1 , wherein A1, A2, E, and F of Chemical Formula A may be identical or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms.

8. The organic light-emitting diode of claim 7 , wherein the substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms is selected from among compounds represented by Structural Formula 10 to Structural Formula 21:

wherein, “-*” for moiety A 1 or A 2 denotes a bonding site for forming a 5-membered ring containing the carbon atom connected to both the substituents R 1 and R 2 , and “-*” for moiety E or F denotes a bonding site for forming a 5-membered ring containing M of the structural Formula Q 1 and Q 2 with moiety A 1 or A 2 ,

when one of the aromatic hydrocarbon rings of Structural Formula 10 to Structural Formula 21 for A 1 or A 2 is bonded to Structural Formula Q 1 or Structural Formula Q 2 , two adjacent carbon atoms of the aromatic hydrocarbon ring occupy respective positions * of Structural Formula Q 1 or Q 2 to form a fused ring; and

R is the same as above defined for R 1 and R 2 , and

m is an integer of 1 to 8, with a proviso that when m is 2 or greater, or R is 2 or greater, the corresponding Rs may be the same or different.

9. The organic light-emitting diode of claim 1 , wherein the linkers L 1 to L 12 in Chemical Formula A represent respective direct bonds, or are each any one selected from among a substituted or unsubstituted arylene of 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene of 2 to 20 carbon atoms.

10. The organic light-emitting diode of claim 9 , wherein the linkers L 1 to L 12 represent respective direct bonds, or are each any one selected from the following Structural Formula 22 to Structural Formula 30, p1 to p4, r1 to r4, and s1 to s4 are each 1 or 2, and x is 1:

wherein hydrogen or deuterium may be positioned on a carbon atom as a member in the aromatic rings of the linkers.

11. The organic light-emitting diode of claim 1 , wherein R 1 to R 9 , and Ar 1 to Ar 8 may be the same or different and are each independently any one selected from among hydrogen, deuterium, a substituted or unsubstituted aryl of 6 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 20 carbon atoms containing at least one heteroatom selected from among O, N, S, and Si, a cyano, and a halogen.

12. The organic light-emitting diode of claim 1 , wherein the amine compound is selected from the group consisting of the compounds represented by the following [Chemical Formula 1] to [Chemical Formula 21]:

13. The organic light-emitting diode of claim 1 , wherein the organic light-emitting diode comprises at least one of 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 emissive layer.

14. The organic light-emitting diode of claim 13 , wherein at least one of the layers is formed using a deposition process or a solution process.

15. The organic light-emitting diode of claim 1 , wherein the organic light-emitting diode comprises two or more emissive layers, the emissive layers including at least one layer employing a phosphorescent material and at least one layer employing the compound represented by Chemical Formula A.

16. The organic light-emitting diode of claim 15 , wherein the phosphorescent material used in the emissive layer is a source of light with a mean wavelength of 550˜620 nm.

17. The organic light-emitting diode of claim 1 , wherein organic light-emitting diode is used for a device selected from among a flat display device, a flexible display device, a monochrome or white flat illumination device, and a monochrome or white flexible illumination device.