Boron compound, and organic light-emitting diode comprising same
The present disclosure relates to a boron compound useful in an organic light-emitting diode and an organic light-emitting diode comprising same and, more particularly, to a boron compound represented by [Chemical Formula A], wherein [Chemical Formula A] and [Chemical Formula C] are as defined in the description.
1. A boron compound represented by the following Chemical Formula A:
wherein,
Q 1 to Q 3 , which may be the same or different, 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 50 carbon atoms,
Y is any one selected from N-R 3 , CR 4 R 5 , O, and S,
X is B, and
R 1 to R 5 , which may be the same or different, are each independently any one selected from a hydrogen atom, a 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 arylamine of 5 to 30 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 nitro, a cyano, and a halogen,
wherein R 1 and R 2 may be connected to each other to form an additional mono- or polycyclic aliphatic or aromatic ring,
and
R 4 and R 5 may be connected to each other to form an additional mono- or polycyclic aliphatic or aromatic ring,
wherein, the term “substituted” in the expression “substituted or unsubstituted” used for compounds of Chemical Formulas A 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, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, an alkylaryl of 7 to 24 carbon atoms, a heteroaryl of 2 to 50 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, and an arylsilyl of 6 to 24 carbon atoms.
2. The boron compound of claim 1 , wherein Y in Chemical Formula A is N-R 3 wherein R 3 is as defined in claim 1 .
3. The boron compound of claim 2 , wherein R 3 is a substituted or unsubstituted aryl of 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms.
4. The boron compound of claim 1 , wherein Y in Chemical Formula A is a linker represented by the following Structural Formula A:
wherein “-* ” denotes a bonding site at which the linker Y bonds to an aromatic carbon atom within the Q 1 and Q 3 ring moieties,
R 41 to R 45 , which are same or different, are each independently any one selected from 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 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 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 5 to 30 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 nitro, a cyano, and a halogen.
5. The boron compound of claim 1 , wherein Y in Chemical Formula A is an oxygen (O) atom.
6. The boron compound of claim 1 , wherein the Q 1 to Q 3 ring moieties, which are same or different, are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms.
7. The boron compound of claim 6 , wherein the aromatic hydrocarbon ring moieties Q 1 and Q 2 in Chemical Formula A are each independently any one selected from compounds represented by the following Structural Formulas 10 to 18:
wherein, “-* ” denotes a bonding site at which a carbon atom in the aromatic ring of Q 1 or Q 2 bonds to X, the linker Y, or the silicon atom (Si),
R's, which are same or different, are each independently a hydrogen, a 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 alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 5 to 30 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, and a halogen, and
m is an integer of 1 to 8, wherein when m is two or more or two or more R's are present, the corresponding R's are same or different.
8. The boron compound of claim 6 , wherein the aromatic hydrocarbon ring of Q 3 in Chemical Formula A is a ring represented by the following Structural Formula B:
wherein “-* ” denotes bonding sites at which the corresponding carbons in the aromatic ring of Q 3 bond to, X, the linker Y, and the silicon atom (Si), respectively, and
R 55 to R 57 , which are same or different, are each independently any one selected from a hydrogen, a 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 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 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 5 to 30 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, and a halogen, and
any adjacent two of R 55 to R 57 can be linked to each to each other to form an additional mono- or polycyclic aliphatic or aromatic ring.
9. The boron compound of claim 1 , wherein the boron compound is any one selected from the following <Compound 1>to <Compound 33>, <Compound 37>to <Compound 54>, and <Compound 56>to <Compound 86>:
10. An organic light-emitting diode, comprising:
a first electrode;
a second electrode facing the second electrode; and
an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the boron compound of claim 1 .
11. The organic light-emitting diode of claim 10 , wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer capable of both hole injection and hole transport, a light-emitting layer, an electron transport layer, and an electron injection layer.
12. The organic light-emitting diode of claim 11 , wherein the organic layer disposed between the first electrode and the second electrode includes a light-emitting layer composed of a host and a dopant, the boron compound represented by Chemical Formula A servings as the dopant.
13. The organic light-emitting diode of claim 12 , wherein the light-emitting layer uses an anthracene derivative represented by the following Chemical Formula C as the host:
wherein,
R 11 to R 18 , which are same or different, are each as defined for R 1 to R 5 in claim 1 ;
Ar 9 and Ar 10 , which are same or different, are each independently any one selected from 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, and a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms;
L 13 , which functions as a linker, is a single bond or is selected from a substituted or unsubstituted arylene of 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene of 2 to 20 carbon atoms; and
k is an integer of 1 to 3, wherein when k is 2 or greater, the corresponding L 13 's are same or different.
14. The organic light-emitting diode of claim 13 , wherein Ar 9 in Chemical Formula C is a substituent represented by the following Chemical Formula C-1:
wherein, R 21 to R 25 , which are same or different, are as defined for R 1 to R 5 in claim 1 ; and can each be linked to an adjacent one to form a saturated or unsaturated cyclic ring.
15. The organic light-emitting diode of claim 13 , wherein L 13 is a single bond or a substituted or unsubstituted arylene of 6 to 20 carbon atoms, and k is 1 or 2, with the proviso that when k is 2, corresponding L 13 's are same or different.
16. The organic light-emitting diode of claim 13 , wherein the anthracene derivative is any one selected from the compounds represented by the following [Chemical Formula C1] to [Chemical Formula C48]:
17. The organic light-emitting diode of claim 11 , wherein at least one selected from among the layers is deposited using a single-molecule deposition process or a solution process.
18. The organic light-emitting diode of claim 10 , 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; and a monochrome or grayscale flexible illumination device.