Compound for organic light-emitting device and organic light-emitting device including same

1. An anthracene derivative, selected from compounds represented by the following Chemical Formula A-1, A-2, B-1, and B-2:

wherein,

in Chemical Formula A-1 and Chemical Formula B-1,

R1 to R8, and R11 to R13 are each hydrogen atom or deuterium,

R14 to R23, which are same or different, are each independently any one selected from among a hydrogen, a deuterium, 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 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 6 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, heteroaryl of 2 to 50 carbon atoms bearing 0, N or S as a heteroatom, 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, a tellurium, an amide, an ether, and an ester,

wherein, the anthracene derivative has the structure of -(L)m-(B)n for at least one of R15 to R17,

L denotes a linker and is a single bond or a deuterium substituted or unsubstituted arylene of 6 to 60 carbon atoms,

B is a deuterium substituted or unsubstituted aryl of 6 to 60 carbon atoms,

m is an integer of 1 to 2, with a proviso that when m is 2, the corresponding L's may be same or different, and

n is an integer of 1 to 5, with a proviso that when n is 2 or greater, the corresponding B's may be same or different,

in Chemical Formula A-2 and Chemical Formula B-2,

R1 to R8, and R12 to R13 are each hydrogen atom or deuterium,

R11, R14 to R23, which are same or different, are each independently any one selected from among a hydrogen, a deuterium, 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 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 6 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, heteroaryl of 2 to 50 carbon atoms bearing 0, N or S as a heteroatom, 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, a tellurium, an amide, an ether, and an ester,

wherein, the anthracene derivative has the structure of -(L)m-(B)n for at least one of R11 and R15 to R17,

L denotes a linker and is a single bond or a deuterium substituted or unsubstituted arylene of 6 to 60 carbon atoms,

B is a deuterium substituted or unsubstituted aryl of 6 to 60 carbon atoms,

m is an integer of 1 to 2, with a proviso that when m is 2, the corresponding L's may be same or different, and

n is an integer of 1 to 5, with a proviso that when n is 2 or greater, the corresponding B's may be same or different,

in Chemical Formula A-1, Chemical Formula A-2, Chemical Formula B-1, and Chemical Formula B-2,

the substituent Ar1 is a substituted or unsubstituted aryl of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms;

two adjacent substituents of R11 to R13 in Chemical Formulas B-1 and B-2 are respective single bonds involved in forming a 5-membered ring as a fused ring with the carbon atom to which the substituents R22 and R23 in Structural Formula Q are both bonded; and

R22 and R23 may be connected to each other to form a ring,

wherein the term ‘substituted’ in the expression “substituted or unsubstituted” means having at least one substituent selected from the group consisting of a deuterium, 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 heteroarylamino of 1 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.

2. The anthracene derivative of claim 1 , wherein the substituents R22 and R23 are same or different and are each be independently a substituted or unsubstituted aryl of 6 to 24 carbon atoms.

3. The anthracene derivative of claim 1 , wherein Ar1 is a substituted or unsubstituted aryl of 6 to 50 carbon atoms.

4. The anthracene derivative of claim 1 , wherein Ar1 is a substituted or unsubstituted aryl of 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl of 3 to 18 carbon atoms.

5. The anthracene derivative of claim 1 , wherein Ar1 is a substituent represented by the following Structural Formula C:

wherein the substituents R21 to R25, which are same or different, are each independently any one selected from among a hydrogen, a deuterium, a halogen, a cyano, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 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 aryl of 6 to 50 carbon atoms, and a substituted or unsubstituted silyl of 1 to 30 carbon atoms, and

‘*’ refers to a bonding site to the anthracene moiety.

6. The anthracene derivative of claim 1 , wherein the anthracene derivative has the structure of -(L)m-(B)n as only one of the substituents R15 to R17 in Chemical Formula A-1 or B-1 and as only one of the substituents R11 and R15 to R17 in Chemical Formula A-2 or B-2.

7. The anthracene derivative of claim 1 , wherein B is any one selected from among a phenyl, a biphenyl, a naphthyl, and a phenanthrene.

8. The anthracene derivative of claim 1 , wherein the linker L is a single bond or any one selected from among any one selected from among the following Structural Formulas 1 to 3:

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

9. The anthracene derivative of claim 5 , wherein the substituents R21 to R25 are each hydrogen or deuterium.

10. The anthracene derivative of claim 1 , wherein the anthracene derivative is any one selected from among the following Compounds 21, 39, 82 to 141, 144, 148 to 156:

11. An organic light-emitting device, including:

a first electrode;

a second electrode facing the first electrode; and

an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes the anthracene derivative of claim 1 .

12. The organic light-emitting device of claim 11 , wherein the organic layer includes 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.

13. The organic light-emitting device of claim 12 , wherein the organic layer disposed between the first and the second electrode is a light-emitting layer composed of a host and a dopant, the anthracene derivative used in the light-emitting layer serving as a host.

14. The organic light-emitting device of claim 12 , wherein at least one selected from the layers is formed using a single-molecule deposition process or a solution process.

15. The organic light-emitting device of claim 11 , wherein the organic light-emitting device is used for a device selected from among a flat display device, a flexible display device, a monochrome or yellow to white flat illumination device, and a monochrome or yellow to white flexible illumination device.

16. An organic light-emitting device, including an anode, a hole transport layer, a light-emitting layer including both a host and a dopant, an electron density control layer containing at least one of the anthracene derivatives selected from compounds represented by the following Chemical Formula A-1, A-2, B-1, and B-2, an electron transport layer, and a cathode in that order,

wherein,

R1 to R8, and R11 to R23, which may be same or different, are each independently any one selected from among a hydrogen, a deuterium, 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 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 6 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, heteroaryl of 2 to 50 carbon atoms bearing 0, N or S as a heteroatom, 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, a tellurium, an amide, an ether, and an ester,

the substituent Ar1 is a substituted or unsubstituted aryl of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms;

two adjacent substituents of R11 to R13 in Chemical Formulas B-1 and B-2 are respective single bonds involved in forming a 5-membered ring as a fused ring with the carbon atom to which the substituents R22 and R23 in Structural Formula Q are both bonded; and

R22 and R23 may be connected to each other to form a ring,

wherein the term ‘substituted in the expression “substituted or unsubstituted” means having at least one substituent selected from the group consisting of a deuterium, 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 heteroarylamino of 1 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.

17. The organic light-emitting device of claim 16 , further including a hole injection layer between the anode and the hole transport layer, and an electron injection layer between the electron transport layer and the cathode.

18. The organic light-emitting device of claim 16 , wherein the anthracene derivative in the electron density control layer is identical to or larger than a material in the electron transport layer in terms of electron mobility.

19. The organic light-emitting device of claim 16 , wherein the affinity A ed (eV) of the electron density control layer falls between the affinity A h (eV) of the host in the light-emitting layer and the affinity A e (eV) of the electron transport layer (A h ≥A ed ≥A e ).

20. The organic light-emitting device of claim 16 , further including a light-emitting layer, made of a blue light-emitting material, a green light-emitting material, or a red light-emitting material, all materials emitting light in a wavelength range of 380 nm to 800 nm, wherein the blue light-emitting material, the green light-emitting material, or the red light-emitting material is a fluorescent or phosphorescent material.