Polymer compound, material for electronic elements, material for organic electroluminescent elements, and organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-10038143-B2
Application number	US-201314428173-A
Country	US
Kind code	B2
Filing date	Sep 13, 2013
Priority date	Sep 14, 2012
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

Provided are a polymer compound, which comprises a copolymer containing at least a unit B, and a unit A and/or a unit C referring to repeating units A, B and C, and which has a weight-average molecular weight of from 50,000 to 1,500,000; a material for electronic devices and a material for organic electroluminescent devices comprising the compound; an organic electroluminescent device having an anode, a cathode and an organic thin film layer, wherein at least one organic thin film layer contains the polymer compound; a coating liquid containing the polymer compound and a solvent; and a method for producing an organic electroluminescent device using the coating liquid. Also provided is a polymer compound suitable to a coating method; a material for electronic devices and a material for organic electroluminescent devices comprising the compound; and an organic EL device, a coating liquid and a method for producing an organic EL device using the compound.

First claim

What is claimed is:

1. A polymer compound, which comprises a copolymer comprising a unit B, and a unit A and/or a unit C, and which has a weight-average molecular weight of from 50,000 to 1,500,000, wherein:
the unit A is a unit comprising, in a main chain thereof, a group selected from the group consisting of an aromatic hydrocarbon cyclic group and an aromatic heterocyclic group, where the groups may be substituted, and
the unit B is a divalent unit of formula (b1), (b2), b3), or (b4):

wherein in the formulae (b1), (b2), (b3), and (b4), * is a position at which the formula bonds to the unit A, B or C;
L is a linking group that constitutes the polymer main chain and bonds the structure of the formula (b1), the formula (b2), the formula (b3), or the formula (b4) except L and the polymer main chain, and is a substituted or unsubstituted aromatic hydrocarbon cyclic group, a substituted or unsubstituted aromatic heterocyclic group, or a combination thereof; with the proviso that when L is an aromatic heterocyclic group comprising an N atom, a number of the N atoms in the atoms constituting one ring of the group is 1 or 2;
each R is independently a substituted or unsubstituted, linear or branched alkyl group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkyl group having a ring carbon atoms of from 3 to 16, a substituted or unsubstituted alkyl ether group having a carbon number of from 1 to 20, a substituted or unsubstituted aryl group having a ring carbon atoms of from 6 to 30, a substituted or unsubstituted alkoxy group having a carbon number of from 1 to 20, a substituted or unsubstituted cycloalkoxy group having a ring carbon atoms of from 3 to 10, a substituted or unsubstituted aryloxy group having a ring carbon atoms of from 6 to 30, a substituted or unsubstituted aralkyl group having a carbon number of from 7 to 40, a substituted or unsubstituted heteroaryl group having a ring atoms of from 3 to 30, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamino group, a substituted silyl group substituted with an aryl group and/or an alkyl group, a halogen atom, a nitro group, a cyano group or a hydroxyl group; and
Ar is a substituted or unsubstituted monovalent aromatic hydrocarbon cyclic group having a ring carbon atoms of from 6 to 30, or a substituted or unsubstituted monovalent aromatic heterocyclic group having a ring atoms of from 5 to 30,
Ar′ is a substituted or unsubstituted divalent aromatic hydrocarbon cyclic group having a ring carbon atoms of from 6 to 30 or a substituted or unsubstituted divalent aromatic heterocyclic group having a ring atoms of from 5 to 30,
the unit C is a unit constituting the polymer main chain and represented by formula (3), (4) or (5); where in the case of formula (5), the formula bonds to the neighboring unit at any of Z 5 , Z 6 , X 3 and Y 3 :

wherein in the formulae (3), (4), and (5), Ar 1 to Ar 3 are each independently a substituted or unsubstituted aromatic hydrocarbon cyclic group, or a substituted or unsubstituted aromatic heterocyclic group;
X 3 and Y 3 are each independently a single bond, CR 1 2 , NR 1 , O, S, or SiR 1 2 ;
R 1 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aromatic hydrocarbon cyclic group, or a substituted or unsubstituted aromatic heterocyclic group;
Z 5 and Z 6 are each independently a substituted or unsubstituted aliphatic hydrocarbon cyclic group, a substituted or unsubstituted aliphatic heterocyclic group, a substituted or unsubstituted divalent aromatic hydrocarbon cyclic group, or a substituted or unsubstituted aromatic heterocyclic group; and
n is an integer of from 1 to 50, and when n is 2 or more, the parenthesized moieties may be the same or different.

2. The polymer compound according to claim l, wherein the unit A is present and the unit A has an unsubstituted alkyl group having a carbon number of from 3 to 16, an alkyl group having one or more phenyl group and having a carbon number of from 1 to 4, a cycloalkyl group having a ring carbon atoms of from 3 to 16 and unsubstituted or substituted with an alkyl group having a carbon number of from 1 to 6, a linear or branched alkyl ether group having a carbon number of from 1 to 20, or a substituted silyl group substituted with at least group selected from the group consisting of alkyl and aryl.

3. The polymer compound according to claim 1 , wherein the unit C is present and the unit C is represented by any of the following formulae (1) to (10):

wherein
X is CR 3 ,
X′ is CR 3 2 , a nitrogen atom in a divalent case NR 3 , a phosphorus atom in a divalent case PR 3 , PO in a divalent case, P(═O)R 3 , O in a divalent case, S in a divalent case, or SiR 3 2 in a divalent case,
R 3 is 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 a ring carbon atoms of from 3 to 16, a substituted or unsubstituted aryl group having a ring carbon acorns of from 6 to 30, or a substituted or unsubstituted heteroaryl group having a ring atoms of from 5 to 30;
multiple R 3 's may bond to form a ring; and
n′ is an integer of from 0 to 5;
with the proviso that instances in which a ring is not formed when n′ is 0 are excluded.

4. The polymer compound according to claim 1 , wherein L, in formulae (b1) to (b4), is a substituted or unsubstituted benzene ring, pyridine ring or pyrimidine ring that bonds at the 1,3-positions to form a main chain, or a structure of formula (a):

wherein X is independently N or CH; and X's on one aromatic ring are not N at the same time, with the proviso that when L is a benzene ring, the 2-position of the benzene ring is unsubstituted.

5. The polymer compound according to claim 1 , which is a polymer compound having the A, the unit B and the unit C.

6. A material for electronic device, comprising the polymer compound according to claim 1 .

7. A material for organic electroluminescent devices, comprising the polymer compound according to claim 1 .

8. An organic electroluminescent device, comprising an anode, a cathode and an organic thin film laver, wherein the organic thin film layer comprises the polymer compound according to claim 1 .

9. The organic electroluminescent device according to claim 8 , comprising a light-emitting layer as the organic thin film layer and the light-emitting layer comprises the polymer compound.

10. A coating liquid comprising the polymer compound according to claim 1 and a solvent.

11. A method for producing an organic electroluminescent device, comprising applying the coating liquid according to claim 10 .

12. The method for producing an organic electroluminescent device according to claim 11 , comprising forming a thin film with the coating liquid by a wet film formation method.

Assignees

• Idemitsu Kosan Co

Inventors

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

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C08G2261/149

  Side-chains having heteroaromatic units · CPC title

• H01L51/0043

  Electricity · mapped topic

• H01L51/0003

  Electricity · mapped topic

• C08G73/0688

  with only one nitrogen atom in the ring, e.g. polyquinolines · CPC title