Polymerizable monomer, and material for organic device, hole injection/transport material, material for organic electroluminescence element and organic electroluminescent element each comprising polymer (polymeric compound) of the polymerizable monomer

Patent metadata

Field	Value
Publication number	US-9425402-B2
Application number	US-201414557946-A
Country	US
Kind code	B2
Filing date	Dec 2, 2014
Priority date	Mar 11, 2009
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

A polymerizable monomer represented by the following formula (1) wherein at least one of Ar 1 to Ar 3 is substituted by a group represented by the following formula (2) and which is substituted by one or more groups comprising a polymerizable functional group.
Ar 1 to Ar 3 are a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, Ar 6 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms and Ar 4 and Ar 5 are a substituted or unsubstituted arylene group having 6 to 40 ring carbon atoms.

First claim

The invention claimed is:

1. A polymerizable monomer represented by the following formula (1) wherein at least one of Ar 1 to Ar 3 is a group selected from the group consisting of groups represented by the following formulas (4) and (6) and which is substituted by one or more groups comprising a polymerizable functional group:

wherein Ar 1 to Ar 3 are independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms:

wherein L 1 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms;
the substituents of L 1 when it is substituted are one or more groups selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring carbon atoms, a heterocyclic group having 3 to 30 ring atoms, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, triarylsilyl group having 18 to 30 ring carbon atoms, a dialkylarylsilyl group or an alkyldiarylsilyl group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, an alkylarylamino group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, a halogen atom, a nitro group, a cyano group and a hydroxyl group;
R 1 and R 2 are independently a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring Carbon atoms, a heterocyclic group having 3 to 30 ring atoms, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a triarylsilyl group having 18 to 30 ring carbon atoms, a dialkylarylsilyl group or an alkyldiarylsilyl group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 carbon atoms, an alkylarylamino group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, a halogen atom, a nitro group, a cyano group and a hydroxyl group;
a is an integer of 0 to 3; and
b is an integer of 0 to 4.

2. A polymerizable monomer represented by the following formula (1) wherein at least one of Ar 1 to Ar 3 is a group represented by the following formula (7), at least one of the remaining groups of Ar 1 to Ar 3 is a group represented by the following formula (3) and which is further substituted by one or more groups comprising a polymerizable functional group:

wherein Ar 1 to Ar 3 are independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms:

wherein L is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms;
the substituents of L 1 when it is substituted are one or more groups selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring carbon atoms, a heterocyclic group having 3 to 30 ring, atoms, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a triarylsilyl group having 18 to 30 ring carbon atoms, a dialkylarylsilyl group or an alkyldiarylsilyl group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, an alkylarylamino group having 8 to 30 carbon atoms where the aryl part has 6 to 20 ring carbon atoms, a halogen atom, a nitro group, a cyano group and a hydroxyl group;
X is a substituted or unsubstituted hetero atom;
substituents of X when it is substituted are one or more groups selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring carbon atoms and a heterocyclic group having 3 to 30 ring atoms;
R 1 and R 2 are independently a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring carbon atoms, a heterocyclic group having 3 to 30 ring atoms, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a triarylsilyl group having 18 to 30 ring carbon atoms, a dialkylarylsilyl group or an alkyldiarylsilyl group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 carbon atoms, an alkylarylamino group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, a halogen atom, a nitro group, a cyano group and a hydroxyl group;
a is an integer of 0 to 3; and
b is an integer of 0 to 4;

wherein R 3 and R 4 are independently a group selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 31 carbon atoms wherein the aryl part has 6 to 30 ring carbon atoms, a heterocyclic group having 3 to 30 ring atoms, a mono- or dialkylamino group having an alkyl group having 1 to 20 carbon atoms, a mono- or diarylamino group having an aryl group having 6 to 30 ring carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a triarylsilyl group having 18 to 30 ring carbon atoms, a dialkylarylsilyl group or an alkyldiarylsilyl group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, an alkylarylamino group having 8 to 30 carbon atoms wherein the aryl part has 6 to 20 ring carbon atoms, a halogen atom, a nitro group, a cyano group and a hydroxyl group;
c and d are independently an integer of 0 to 4;
L 2 is a substituted or unsubstituted arylene group having 10 to 50 ring carbon atoms; and
the substituents of L 2 when i

Assignees

• Idemitsu Kosan Co

Inventors

• Eida Mitsuru
• Yabunouchi Nobuhiro
• Mizuki Yumiko
• Watanabe Masami
• Yomogita Akinori

Classifications

• H10K85/111

  comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene · CPC title

• C07D207/452 Primary

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title

• H01L51/5088

  Electricity · mapped topic

• C07D333/76

  Dibenzothiophenes · CPC title

• H01L51/0073

  Electricity · mapped topic