Organic light-emitting diode with high efficiency

1. An organic light-emitting diode, comprising:

a first electrode;

a second electrode facing the first electrode; and

a light-emitting layer and an electron transport layer sequentially arranged between the first and the second electrode,

wherein the light-emitting layer contains at least one of the amine compounds represented by following Chemical Formula A or Chemical Formula B, and the electron transport layer contains at least one of the compounds represented by the following Chemical Formula E:

wherein,

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 within the aromatic ring A 1 and two adjacent carbon atoms within the aromatic ring A 2 form a 5-membered fused ring with a carbon atom to which the substituents R 1 and R 2 are both bonded;

linkers L 1 to L 12 may be the same or different, and are each independently selected from among a single bond and substituted or unsubstituted arylene of 6 to 60 carbon atoms;

M is any one selected from among N—R 3 , CR 4 R 5 , O, and S;

R 1 to R 5 , 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 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 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 the proviso that R 1 and R 2 may be bonded to each other to form a mono- or polycyclic aliphatic or aromatic ring, which may be a heterocyclic ring containing at least one heteroatom selected from among N, O, P, Si, and S as a ring member;

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

in Chemical Formula A, x is 1, and y and z are the same or different and are each independently an integer of 0 or 1 wherein y+z is not zero;

in Chemical Formula B, x is 1, and y and z are the same or different and are each independently an integer of 0 or 1; and

respective rings may be formed through linkages between Ar 1 and Ar 2 , between Ar 3 and Ar 4 , between Ar 5 and Ar 6 , and between Ar 7 and Ar 8 ;

two adjacent carbon atoms of the A 2 ring moiety of Chemical Formula A may occupy respective positions * of Structural Formula Q 1 to form a fused ring; and

two adjacent carbon atoms of the A 1 ring moiety of Chemical Formula B may occupy respective positions * of structural Formula Q 2 to form a fused ring, and two adjacent carbon atoms of the A 2 ring moiety of Chemical Formula B may occupy respective positions * of Structural Formula Q 1 to form a fused ring; and

wherein, Ar 11 , Ar 12 , and Ar 13 may be the same or different, and are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, with the proviso that when Ar 12 is a hydrogen or deuterium atom, Ar 13 is neither a hydrogen atom nor a deuterium atom,

A is a monovalent substituent represented by the following Structural Formula A:

wherein Ar 10 is a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms,

R 11 to R 14 may be the same or different, and are each independently any one selected from among a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms,

wherein ‘substituted’ in an expression ‘substituted or unsubstituted’ used in Chemical Formulas A, B, and E means having at least one substituent selected from the group consisting of a deuterium atom, a cyano, a halogen, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms or a heteroarylalkyl of 2 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, and an arylsilyl of 6 to 24 carbon atoms.

2. The organic light-emitting diode of claim 1 , wherein the compound represented by Chemical Formula E is a compound represented by the following Chemical Formula E-1:

wherein Ar 11 to Ar 13 and A are each as defined in claim 1 .

3. The organic light-emitting diode of claim 1 , wherein the compound represented by Chemical Formula E is a compound represented by the following Chemical Formula E-2:

wherein Ar 11 to Ar 13 and A are each as defined in claim 1 .

4. The organic light-emitting diode of claim 1 , wherein A 1 , A 2 , E, and F in Chemical Formula A or B may be same or different and are each independently substituted or unsubstituted aromatic hydrocarbon rings of 6 to 50.

5. The organic light-emitting diode of claim 4 , wherein the substituted or unsubstituted aromatic hydrocarbon rings of 6 to 50 carbon atoms may be same or different and are each independently any one selected from among the compounds represented by the following [Structural Formula 10] to [Structural Formula 21]:

wherein

“-*” denotes a bonding site for forming a 5-membered ring bearing a carbon atom which is connected to both the substituents R 1 and R 2 or a bonding site for forming a 5-membered ring bearing M of the Structural Formulas Q 1 and Q 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's are the same as defined above 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 two or more R's exist, the corresponding R's may be the same or different.

6. The organic light-emitting diode of claim 1 , wherein linkers Li to Liz in Chemical Formulas A and B are a single bond or any one selected from among the compounds represented by the following [Structural Formula 22], [Structural Formula 23], [Structural Formula 25], [Structural Formula 27], [Structural Formula 28], and [Structural Formula 30]:

wherein each of the unsubstituted carbon atoms of the aromatic ring moiety may be bound with a hydrogen atom or a deuterium atom.

7. The organic light-emitting diode of claim 1 , wherein the Structural Formula A is the following [Structural Formula A-1]:

wherein R 11 to R 14 , and Ar 10 are each as defined in claim 1 .

8. The organic light-emitting diode of claim 1 , wherein the amine Compound is any one selected from among the compounds represented by [Chemical Formula 1] to [Chemical Formula 239]:

9. The organic light-emitting diode of claim 1 , wherein the compound represented by [Chemical Formula E] is any one selected from the group consisting of the following [Compound 1] to [Compound 63]:

10. The organic light-emitting diode of claim 1 , wherein the first electrode is an anode, the second electrode is a cathode, the light-emitting layer and the electron transport layer are sequentially arranged between the anode and the cathode, and an electron density control layer is further arranged between the light-emitting layer and the electron transport layer.

11. The organic light-emitting diode of claim 10 , wherein the electron density control layer includes a compound represented by any one of the following Chemical Formulas F to H:

wherein,

R 31 to R 38 , and R 41 to R 53 may be the same or different, and are each independently any one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 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 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 aryl of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms bearing 0, N or S as a hetero atom, a cyano, a nitro, a halogen, a substituted or unsubstituted alkyl silyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkyl germanium of 1 to 30 carbon atoms, a substituted or unsubstituted alkyl boron of 1 to 30 carbon atoms, a substituted or unsubstituted alkyl aluminum of 1 to 30 carbon atoms, a carbonyl, a phosphoryl, an amino, a thiol, a hydroxy, a selenium atom, a tellurium atom, an amide, an ether, and an ester;

Ar 21 is a substituted or unsubstituted aryl of 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms;

wherein adjacent two of the substituents R 41 to R 43 or adjacent two of the substituents R 44 to R 47 in Chemical Formula G are respective single bonds to form a 5-membered ring as a fused ring together with a carbon to which substituents R 52 and R 53 of Structural Formula Q are bonded, wherein a bond may be formed between the substituents R 52 and R 53 to form respective rings;

wherein,

R 61 to R 65 may be the same or different, and are each independently any one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 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 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 aryl thioxy of 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 5 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms bearing 0, N or S as a hetero atom, a cyano, a nitro, a halogen, a substituted or unsubstituted silyl of 1 to 30 carbon atoms, a substituted or unsubstituted germanium of 1 to 30 carbon atoms, a substituted or unsubstituted boron of 1 to 30 carbon atoms, a substituted or unsubstituted aluminum of 1 to 30 carbon atoms, a carbonyl, a phosphoryl, an amino, a thiol, a hydroxy, a selenium atom, a tellurium atom, an amide, an ether, and an ester, with the proviso that a hydrogen atom is positioned on each of the aromatic ring carbon atoms to which none of the substituents R 61 to R 65 are bonded;

the linker L is a single bond or a substituted or unsubstituted arylene of 6 to 60 carbon atoms;

j is an integer of 0 to 2;

k is an integer of 1 to 5;

l to n may be the same or different, and are each independently an integer of 1 to 4;

o is an integer of 1 to 3, with the proviso that when each of k to o is 2 or greater, corresponding R 61 's to R 65 's may be the same or different;

‘***’ denotes a bonding site for bonding the linker L;

wherein the term ‘substituted’ in the expression ‘substituted or unsubstituted’ used in Chemical Formulas F to H 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 alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms or a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, an arylamino of 6 to 24 carbon atoms, a hetero arylamino of 2 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24 carbon atoms, and an aryloxy of 6 to 24 carbon atoms.

12. The organic light-emitting diode of claim 10 , wherein at least one selected from among a hole injection layer and a hole transport layer is arranged between the anode and the light-emitting layer, and an electron injection layer is optionally arranged between the electron transport layer and the cathode.

13. The organic light-emitting diode of claim 12 , wherein at least one of the layers arranged between the anode and the cathode is formed using a deposition process or a solution process.

14. The organic light-emitting diode of claim 1 , 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.