Azaborinine derivatives, their synthesis and use in organic electronic devices

Patent metadata

Field	Value
Publication number	US-2016248014-A1
Application number	US-201415025768-A
Country	US
Kind code	A1
Filing date	Sep 16, 2014
Priority date	Sep 30, 2013
Publication date	Aug 25, 2016
Grant date	—

Abstract

The present invention relates to azaborinine derivatives their synthesis as well as their use in organic electronic devices, particularly in organic light emitting devices, organic photovoltaic devices and organic photodetectors. The invention further relates to organic electronic devices comprising the present azaborinine derivatives

First claim

1 . Compound comprising a structural unit of formula (I-1 or I-2)

wherein
A 1 and A 2 are independently of each other mono- or polycyclic aromatic or heteroaromatic ring systems annealed to the neighboring azaborinine ring;
B 1 is a mono- or polycyclic aromatic or heteroaromatic ring system annealed to the two neighboring azaborinine rings;
Ar 1 and Ar 2 are independently of each other aryl or heteroaryl; and
R 1 and R 2 are independently of each other selected from the group consisting of hydrogen, carbyl and hydrocarbyl;
wherein A 1 , A 2 , B 1 , Ar 1 and Ar 2 may independently of each other be substituted or unsubstituted.

2 . Compound according to claim 1 , wherein each of A 1 and A 2 comprises from 5 to 30 aromatic ring atoms.

3 . Compound according to claim 1 , wherein A 1 and A 2 are independently of each other selected from cyclopentadiene, mono-, di-, tri- and tetracyclic aromatic or heteroaromatic ring systems and their respective derivatives wherein one or more aromatic ring atom may be replaced by N and/or one or more of the non-aromatic ring atoms may be replaced by a group selected from O, S, Se, NR 3 and SiR 3 2 , preferably selected from O, S, NR 3 and SiR 3 2 , more preferably selected from O, S and NR 3 , with R 3 being at each occurrence independently of each other H or optionally substituted C 1-40 carbyl or hydrocarbyl

4 . Compound according to claim 1 , wherein B 1 is selected from the group consisting of Ar 3 , Ar 4 -Ar 5 and Ar 6 -Ar 7 -Ar 8 , wherein Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , and Ar 8 are independently of each other mono- or polycyclic aromatic or heteroaromatic ring systems, which may be substituted or unsubstituted.

5 . Compound according to claim 1 , wherein B 1 is selected from the group consisting of Ar 3 , Ar 4 -Ar 5 and Ar 6 -Ar 7 -Ar 8 , wherein Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , and Ar 8 are independently of each other selected from the group consisting of benzene, napthalene, anthracene, phenantrene, phenalene, tetracene, pyrene, chrysene, linear and angular pentacene, linear and angular hexacene, cyclopentadiene, indene, indacene, fluorene, acenaphthylene and the respective derivatives wherein one or more aromatic ring atoms may be replaced by N and/or one or more of the non-aromatic ring atoms may be replaced by a group selected from O, S, Se, NR 3 , CR 3 2 and SiR 3 2 , preferably selected from O, S, NR 3 and SiR 3 2 , more preferably selected from O, S and NR 3 , with R 3 being at each occurrence independently of each other H or optionally substituted C 1-40 carbyl or hydrocarbyl.

6 . Compound according to claim 1 , wherein B 1 is selected from the group consisting of Ar 3 , Ar 4 -Ar 5 and Ar 6 -Ar 7 -Ar 8 , wherein Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 , and Ar 8 are independently of each other selected from the group consisting of benzene, naphthalene, cyclopentadiene, indene and their respective derivatives wherein one or more aromatic ring atoms may be replaced by N and/or one or more of the non-aromatic ring atoms may be replaced by a group selected from O, S, Se, NR 3 , CR 3 2 and SiR 3 2 , preferably selected from O, S, NR 3 and SiR 3 2 , more preferably selected from O, S and NR 3 , with R 3 being at each occurrence independently of each other H or optionally substituted C 1-40 carbyl or hydrocarbyl.

7 . Compound according to claim 1 , wherein each of Ar 1 and Ar 2 comprises from 5 to 30 aromatic carbon atoms.

8 . Compound according claim 1 , wherein Ar 1 and Ar 2 are independently of each other selected from cyclopentadiene, mono-, di-, tri- and tetracyclic aromatic or heteroaromatic ring systems and their respective derivatives wherein one or more aromatic ring atom may be replaced by N and/or one or more of the non-aromative ring atoms may be replaced by a group selected from O, S, Se, NR 3 and SiR 3 2 , preferably selected from O, S, NR 3 and SiR 3 2 , more preferably selected from O, S and NR 3 , with R 3 being at each occurrence independently of each other H or optionally substituted C 1-40 carbyl or hydrocarbyl.

9 . Compound according to claim 1 , wherein R 1 and R 2 are independently of each other selected from the group consisting of H, alkyl having from 1 to 20 carbon atoms and aryl having from 5 to 30 carbons atoms and heteroaryl having from 5 to 30 aromatic ring atoms.

10 . Compound according to claim 1 , wherein the compound is selected from the group consisting of

wherein R 4 is at each occurrence selected from the group consisting of H, F and alkyl having from 1 to 20 carbon atoms.

11 . Compound according to claim 1 , wherein the compound is selected from the group consisting of small molecule, monomer, oligomer and polymer.

12 . A mixture or a blend comprising one or more compounds of claim 1 and one or more compounds or polymers having semiconducting, charge transport, hole transport, electron transport, hole blocking, electron blocking, electrically conducting, photoconducting or light emitting properties.

13 . Formulation comprising the compound of claim 1 and an organic solvent.

14 . A method comprising incorporating a compound of claim 1 as charge transport, semiconducting, electrically conducting, photoconducting or light emitting material in optical, electrooptical, electronic, electroluminescent or photoluminescent components or devices.

15 . Charge transport, semiconducting, electrically conducting, photoconducting or light emitting material comprising the compound of claim 1 .

16 . A component or device comprising the compound of claim 1 , said component or device being selected from the group consisting of organic field effect transistors (OFET), thin film transistors (TFT), integrated circuits (IC), logic circuits, capacitors, radio frequency identification (RFID) tags, devices or components, organic light emitting diodes (OLED), organic light emitting transistors (OLET), flat panel displays, backlights of displays, organic photovoltaic devices (OPV), organic solar cells (O-SC), photodiodes, laser diodes, photoconductors, organic photodetectors (OPD), electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, charge injection layers, charge transport layers or interlayers in polymer light emitting diodes (PLEDs), Schottky diodes, planarising layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates, conducting patterns, electrode materials in batteries, alignment layers, biosensors, biochips, security markings, security devices, and components or devices for detecting and discriminating DNA sequences.

17 . A component or device according to claim 16 , said component or device being selected from the group consisting of organic field effect transistors (OFET), thin film transistors (TFT), integrated circuitry (IC), radio frequency identification (RFID) tags, organic light emitting devices (OLED), organic light emitting transistors (OLET) and backlights of displays.

Assignees

• Merck Patent Gmbh

Inventors

• Zhang Fan
• Wang Xinyang
• Tang Ruizhi
• Fu Yubin
• Zhuang Xiaodong
• Feng Xinliang
• Wu Dongqing

Classifications

• C09K2211/1051

  with sulfur · CPC title

• C09K2211/104

  with other heteroatoms · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/1055

  with other heteroatoms · CPC title

• C09K2211/1048

  with oxygen · CPC title