Boron compound and organic light-emitting diode comprising same

Patent metadata

Field	Value
Publication number	US-12030900-B2
Application number	US-201917291978-A
Country	US
Kind code	B2
Filing date	Nov 19, 2019
Priority date	Nov 20, 2018
Publication date	Jul 9, 2024
Grant date	Jul 9, 2024

Abstract

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] or [Chemical Formula B], wherein [Chemical Formula A] and [Chemical Formula B] are as defined in the description.

First claim

The invention claimed is:

1. A boron compound represented by the following Chemical Formula A or B:

wherein,
Q 1 to Q 3 , which are 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, and
R 1 to R 5 , which are 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 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,
R 3 to R 5 can each be connected to the Q 2 ring moiety or Q 3 ring moiety to form an additional mono- or polycyclic aliphatic or aromatic ring and
R 4 and R 5 can 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 and B 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, 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, 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, and an arylsilyl of 6 to 24 carbon atoms.

2. The boron compound of claim 1 , wherein Y in Chemical Formulas A and B 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 Formulas A and B 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 2 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 Formulas A and B is an oxygen (O) atom.

6. The boron compound of claim 1 , wherein X in Chemical Formulas A and B is a boron (B) atom.

7. 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.

8. The boron compound of claim 7 , wherein the aromatic hydrocarbon ring moiety Q 2 in Chemical Formula A is any one selected from compounds represented by the following Structural Formulas 10 to 21; and
the aromatic hydrocarbon ring moieties Q 1 and Q 2 in Chemical Formula B are same or different and are each independently any one selected from compounds represented by the following Structural Formulas 10 to 21:

wherein, “-*” denotes a bonding site at which a carbon atom in the aromatic ring of Q 1 or Q 2 bonds to X, nitrogen (N) atom, or the linker Y,
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 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
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.

9. The boron compound of claim 7 , wherein the aromatic hydrocarbon rings of Q 1 and Q 3 in Chemical Formula A are same or different and are each independently a ring represented by the following Structural Formula B:

wherein “-*” denotes bonding sites at which the corresponding carbons in the aromatic ring of Q 1 bond to the carbon atom linked to R 1 , the nitrogen (N) atom, and X, respectively or at which the corresponding carbons in the aromatic ring in Q 3 bond to the nitrogen (N) atom, X, and the linker Y, 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 alky

Assignees

• Sfc Co Ltd

Inventors

• Lee Se-Jin
• Lee Bong-Hyang
• Yu Taejung
• Choi Yeong-Tae
• Kim Kyung-Tae

Classifications

• H10K85/658

  Organoboranes · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title