Copolymer, material for organic electronic element, material for organic electroluminescent element, and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9847490-B2
Application number	US-201314434558-A
Country	US
Kind code	B2
Filing date	Oct 2, 2013
Priority date	Oct 9, 2012
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

Provided are a copolymer having plural repeating units each having a specific structure, and having a weight-average molecular weight of from 100,000 to 3,000,000; a material for organic electronic devices and a material for organic electroluminescent devices containing the copolymer; a solution containing the copolymer and a solvent; and an organic electroluminescent device using the material for organic electroluminescent devices. The copolymer has not only charge transporting properties but also solubility and is suitable for forming a film according to a coating method. The present invention provides the copolymer, and a material for organic electronic devices and a material for organic electroluminescent devices containing the copolymer, an organic electroluminescent device, and a solution containing the copolymer.

First claim

What is claimed is:

1. A copolymer, consisting essentially of:
at least one repeating unit according to formula (1); and
at least one repeating unit according to formula (2);
wherein:
the copolymer has a weight-average molecular weight of 100,000 to 3,000,000;
formula (1) is:

wherein:
A represents a hydrogen atom or a substituted or unsubstituted alkyl group having a carbon number of from 1 to 10;
each X 1 independently represents a single bond, O (oxygen atom), S (sulfur atom), a substituted or unsubstituted alkylene group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having a carbon number of from 1 to 20, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted oxyarylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkylene group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroaiylene group having 5 to 30 ring atoms, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, or a substituted silylene group substituted with a substituent selected from alkyl and aryl;
each of X 2 , Y 1 and Y 2 independently represents a single bond, CR 2 2 , CR 2 , NR 2 , N, O, S, or SiR 2 2 ;
each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted silyl group substituted with one or more substituents selected from alkyl and aryl, a halogen atom, a nitro group, a cyano group, or a hydroxyl group, provided that R 2 bonding to a nitrogen atom is not a hydrogen atom;
each of Z 1 to Z 5 independently represents a substituted or unsubstituted aliphatic hydrocarbon cyclic group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aliphatic heterocyclic group having 3 to 30 ring atoms, a substituted or unsubstituted aromatic hydrocarbon cyclic group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms;
a, b, d, e, f, g, p, q, m and n each independently indicate an integer of from 0 to 5;
R 1 represents a single bond, a substituted or unsubstituted alkyl group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, or a substituted silyl group substituted with a substituent selected from alkyl and aryl;
L 1 represents a single bond, a substituted or unsubstituted alkylene group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted oxyalkylene group having a carbon number of from 1 to 20, a substituted or unsubstituted oxycycloalkylene group having 3 to 16 ring carbon atoms, a substituted or unsubstituted oxyarylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aralkylene group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, or a substituted silylene group substituted with a substituent selected from alkyl and aryl; and
when L 1 and R 1 bond, the formula contains a repeating unit where a=0 and b=0; and
formula (2) is:

wherein:
A in formula (2) is the same as A in formula (1);
c indicates an integer of from 0 to 5;
L 2 represents a single bond, a substituted or unsubstituted alkylene group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkylene group having 3 to 16, a substituted or unsubstituted arylene group having 6 to 50, a substituted or unsubstituted aralkylene group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a substituted silylene group substituted with a substituent selected from alkyl and aryl;
L 2 is not a tricyclic or more polycyclic nitrogen-containing heteroarylene group;
R 3 represents a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted phenanthrolinyl group, the substituted groups having a substituent selected from a phenyl group, a 4-octylphenyl group, a 4-cyanophenyl group, a di-octylfluorenyl group, a dibenzofuranyl group, and a pyridinyl group.

2. The copolymer according to claim 1 , the formula (1) is represented by formula (3):

wherein A, X 1 , X 2 , Y 1 , Y 2 , Z 1 to Z 5 , L 1 , a, d, e, f, g, p, q, m and n each are independently the same as in formula (1).

3. The copolymer according to claim 1 , wherein c is 0.

4. The copolymer according to claim 1 , wherein formula (1) is represented by formula (4) or (5):

wherein:
A, L 1 , R 1 , R 2 and a each are independently the same as in formula (1);
Y 3 represents a single bond, CR 2 , N, O or S; and
Q represents CR 2 or N.

5. The copolymer according to claim 1 , wherein formula (1) is represented by the following formula (6) or (7):

wherein:
A, L 1 , R 1 and a are the same as in formula (1);
t indicates an integer of from 0 to 3;
r, s and u each indicate an integer of from 0 to 4; and
R 4 and R 5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkyl group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkoxy group having 3 to 16 ring carbon atoms, a substituted or unsubstituted aryloxy

Assignees

• Idemitsu Kosan Co

Inventors

• Yomogita Akinori
• Matsuo Shigeru
• Ono Hidetoshi
• Ikeda Kiyoshi
• Kawakami Hironori
• Matsuura Masahide
• Ito Mitsunori

Classifications

• C08F226/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08F212/32 Primary

  containing two or more rings · CPC title

• C08F12/26

  Nitrogen · CPC title

• C08F212/26

  Nitrogen · CPC title

• C08F212/12

  Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical · CPC title