Organic electroluminescence device and ink composition

Patent metadata

Field	Value
Publication number	US-9815997-B2
Application number	US-201514679589-A
Country	US
Kind code	B2
Filing date	Apr 6, 2015
Priority date	Apr 8, 2014
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

An organic electroluminescence device including: an anode and a cathode; and at least one organic thin film layer between the anode and the cathode, wherein one of the organic thin film layer(s) comprises a polymer represented by the following formula (1).

First claim

The invention claimed is:

1. An organic electroluminescence device comprising:
an anode and a cathode; and
at least one organic thin film layer between the anode and the cathode,
wherein one of the organic thin film layer(s) comprises a polymer represented by the following
formula (2):

wherein in the formula (2),
R 1 and R 2 are independently a hydrogen atom, an alkyl group including 1 to 8 carbon atoms, a cycloalkyl group including 5 to 6 carbon atoms, an alkoxy group including 1 to 8 carbon atoms, an aryl group including 6 to 10 ring carbon atoms, an aryloxy group including 6 to 10 ring carbon atoms, a fluorine atom, a chlorine atom, an alkoxyalkyl group including 2 to 16 carbon atoms, a substituted or unsubstituted amino group or a substituted or unsubstituted mercapto group;
R 1 and R 2 may independently be bonded to another atom to form a ring or may be bonded to each other to form a ring;
X 1 is —O— or —S—;
R 3 is an alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 8 carbon atoms, a substituted or unsubstituted alkyl carbonyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 10 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 10 carbon atoms, a substituted or unsubstituted arylcarbonyl group including 6 to 10 carbon atoms or a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms;
R 4 is a hydrogen atom, an alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 8 carbon atoms, a substituted or unsubstituted alkyl carbonyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 10 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 10 carbon atoms, a substituted or unsubstituted arylcarbonyl group including 6 to 10 carbon atoms or a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms;
n is an integer of 10 to 3000;
L 1 is a single bond or a group represented by the following formula (2′) or the following formula (3′);
-L 11 -L 12 -L 13 -  (2′)

wherein in the formula (2′), L 11 is an alkylene group including 1 to 8 carbon atoms; L 12 is a single bond, —O— or —S— and L 13 is a single bond or an alkylene group including 1 to 8 carbon atoms; and L 11 is bonded to R 4 ;
-L 14 -L 15 -B-L 16 -(3′)

wherein in the formula (3′), L 14 is a single bond or an alkylene group including 1 to 8 carbon atoms; L 15 is a single bond, —O— or —S—, B is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocyclic ring; L 16 is a single bond, —O— or —S—, and L 14 is bonded to R 4 .

2. The organic electroluminescence device according to claim 1 , wherein R 4 is an alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 8 carbon atoms, a substituted or unsubstituted alkyl carbonyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 10 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 10 carbon atoms, a substituted or unsubstituted arylcarbonyl group including 6 to 10 carbon atoms or a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms.

3. The organic electroluminescence device according to claim 1 , wherein R 3 and R 4 are independently a substituted or unsubstituted aryl group including 6 to 10 carbon atoms or a substituted or unsubstituted arylcarbonyl group including 6 to 10 carbon atoms.

4. The organic electroluminescence device according to claim 1 , wherein R 1 and R 2 are independently a hydrogen atom, an alkyl group including 1 to 8 carbon atoms, a cycloalkyl group including 5 to 6 carbon atoms, an alkoxy group including 1 to 8 carbon atoms, an aryl group including 6 to 10 ring carbon atoms, an aryloxy group including 6 to 10 ring carbon atoms or an alkoxyalkyl group including 2 to 16 carbon atoms.

5. The organic electroluminescence device according to claim 1 , wherein R 1 and R 2 are independently an alkyl group including 1 to 8 carbon atoms, an alkoxy group including 1 to 8 carbon atoms or an aryl group including 6 to 10 ring carbon atoms.

6. The organic electroluminescence device according to claim 1 , wherein X 1 is —O—.

7. The organic electroluminescence device according to claim 1 , wherein L 1 is a single bond.

8. The organic electroluminescence device according to claim 1 , wherein a polymer represented by the formula (2) is a polymer represented by the following formula (3):

wherein in the formula (3), R 1 to R 4 and n are as defined for R 1 to R 4 and n in the formula (2).

9. The organic electroluminescence device according to claim 1 , wherein the polymer represented by the formula (2) is a polymer represented by the following formula (4):

wherein in the formula (4), R 1 , R 2 and n are as defined for R 1 , R 2 and n in the formula (2); and Ar 3 and Ar 4 are independently an aryl group including 6 to 10 ring carbon atoms.

10. The organic electroluminescence device according to claim 1 , wherein the layer comprising the polymer represented by the formula (2) is an emitting layer.

11. The organic electroluminescence device according to claim 1 , wherein the layer comprising the polymer represented by the formula (2) comprises said polymer in an amount of 1 to 80 wt %.

12. An ink composition comprising the polymer represented by the following formula (2) and an organic semiconductor material;

wherein in the formula (2),
R 1 and R 2 are independently a hydrogen atom, an alkyl group including 1 to 8 carbon atoms, a cycloalkyl group including 5 to 6 carbon atoms, an alkoxy group including 1 to 8 carbon atoms, an aryl group including 6 to 10 ring carbon atoms, an aryloxy group including 6 to 10 ring carbon atoms, a fluorine atom, a chlorine atom, an alkoxyalkyl group including 2 to 16 carbon atoms, a substituted or unsubstituted amino group or a substituted or unsubstituted mercapto group;
R 1 and R 2 may independently be bonded to another atom to form a ring or may be bonded to each other to form a ring;
X 1 is —O— or —S—;
R 3 is an alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 8 carbon atoms, a substituted or unsubstituted alkyl carbonyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 10 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 10 carbon atoms, a substituted or unsubstituted arylcarbonyl group including 6 to 10 carbon atoms or a substituted or unsubstituted aralkyl group including 7 to 20 carbon atoms;
R 4 is a hydrogen atom, an alkyl group including 1 to 8 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 8 carbon atoms, a substituted or unsubstituted alkyl carbonyl group including 1 to 8 carbon atoms, a substituted or unsubstituted aryl group including 6 to 10 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 10 carbon atoms, a substituted or unsubs

Assignees

• Idemitsu Kosan Co

Inventors

• Kawakami Hironori
• Matsuo Shigeru

Classifications

• C08G65/485

  Polyphenylene oxides · CPC title

• H01L51/0005

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• C09D11/52 Primary

  Electrically conductive inks · CPC title

• H01L51/0003

  Electricity · mapped topic