Organic heterocyclic compound and light-emitting diode comprising same

Patent metadata

Field	Value
Publication number	US-11279693-B2
Application number	US-201615772122-A
Country	US
Kind code	B2
Filing date	Nov 1, 2016
Priority date	Nov 13, 2015
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

The present disclosure relates to an organic compound represented by Chemical Formula A or B, and an organic light-emitting diode comprising the same.

First claim

The invention claimed is:

1. An organic compound, represented by the following Chemical Formula A or B:

wherein,
A1, A2, 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 Al and two adjacent carbon atoms of the aromatic ring A2 form a 5-membered fused ring together with a carbon atom connected to both substituents R1 and R2;
linkers L1 and L2 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—R3, CR4R5, SiR6R7, GeR8R9, O, S, and Se;
Ar1 and Ar2 may be the same or different and are each independently a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms bearing at least one nitrogen atom,
n1 and n2 are each independently an integer of 1 to 3, with the proviso that when each of them is two or greater, the corresponding respective L1's and L2's are the same or different,
x is 1 and y is 0, or x and y are each 1,
R1 to R9 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 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 the proviso that R1 and R2 in Chemical Formula A are not bonded to each other, and R1 and R2 in Chemical Formula B may be bonded to each other to form a mono- or polycyclic aliphatic or aromatic ring, which may be a heterocyclic ring bearing at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te as a ring member;
two adjacent carbon atoms of the A2 ring moiety of Chemical Formula A may occupy respective positions * of Structural Formula Q1 to form a fused ring, and
two adjacent carbon atoms of the A1 ring moiety of Chemical Formula B may occupy respective positions * of structural Formula Q2 to form a fused ring, and two adjacent carbon atoms of the A2 ring moiety of Chemical Formula B may occupy respective positions * of Structural Formula Q1 to form a fused ring;
wherein the term “substituted” in the expression “substituted or unsubstituted” used for 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 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 carnon atoms, an arylsilyl of 6 to 24 carbon atoms, and an aryloxy of 6 to 24 carbon atoms.

2. The compound of claim 1 , wherein A 1 , A 2 , E, and F in Chemical Formula A or B may be the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms.

3. The compound of claim 2 , wherein the substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms may be independently selected from among compounds represented by Structural Formulas 10 to 21:

wherein,
“-*” denotes a bonding site for forming a 5-membered ring bearing the carbon atom connected to the substituents R 1 and R 2 or a bonding site for forming a 5-membered ring bearing M of 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 Q 2 , two adjacent carbon atoms of the aromatic hydrocarbon ring occupy respective positions * of Structural Formula Qi or Q 2 to form a fused ring;
R's are the same as defined in claim 1 ; and
m is an integer of 1 to 8, with the 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.

4. The compound of claim 1 , wherein the linkers L 1 and L 2 in Chemical Formula A or B are each a single bond or one selected from among compounds represented by the following Structural Formulas 22 to 30, and n1 and n2 are each 1 or 2:

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

5. The compound of claim 4 , wherein x is 1 and y is 0 in Chemical Formulas A and B.

6. The compound of claim 1 , wherein when substituents Ar 1 and Ar 2 in Chemical Formulas A and B are each a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms bearing at least one nitrogen atoms, the substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms is any one selected from among the following Structural Formulas 1 to 3:

wherein
T 1 to T 6 may be the same or different and are each independently one selected from among C(R 11 ), C(R 11 )(R 12 ), N, N(R 13 ), O, and S; and
R 11 to R 13 , R 21 , and R 22 may be the same or different and are each independently 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 aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, and a substit

Assignees

• Sfc Co Ltd

Inventors

• Cha Soon-Wook
• Yoo Jung-Ho
• Kim Ji-Hwan
• Park Sang-Woo
• Shin Yoona
• Lim Jea-Geon

Classifications

• C07D517/20

  Spiro-condensed systems · CPC title

• C07D495/12

  in which the condensed system contains three hetero rings · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07D307/77 Primary

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title

• C07D493/20

  Spiro-condensed systems · CPC title