Varnish for formation of charge-transporting thin film

Patent metadata

Field	Value
Publication number	US-10301484-B2
Application number	US-201615544804-A
Country	US
Kind code	B2
Filing date	Jan 19, 2016
Priority date	Jan 20, 2015
Publication date	May 28, 2019
Grant date	May 28, 2019

Abstract

Provided is a varnish for the formation of a charge-transporting thin film, said varnish including an organic solvent, a charge-transporting substance, and a 2,2,6,6-tetraalkylpiperidine-N-oxyl derivative represented by formula (T1)

(in the formula, each R A independently represents a C1-20 alkyl group, and R B represents a hydrogen atom, a hydroxy group, an amino group, a carboxyl group, a cyano group, an oxo group, an isocyanato group, a C1-20 alkoxy group, a C2-20 alkylcarbonyloxy group, a C7-20 arylcarbonyloxy group, a C2-20 alkylcarbonylamino group or a C7-20 arylcarbonylamino group).

First claim

The invention claimed is:

1. A charge-transporting thin film-forming varnish comprising a 2,2,6,6-tetraalkylpiperidine-N-oxyl derivative of formula (T1), a charge-transporting substance and an organic solvent

(wherein each R A is independently an alkyl group of 1 to 20 carbon atoms; and R B is a hydrogen atom, a hydroxyl group, an amino group, a carboxyl group, a cyano group, an oxo group, an isocyanato group, an alkoxy group of 1 to 20 carbon atoms, an alkylcarbonyloxy group of 2 to 20 carbon atoms, an arylcarbonyloxy group of 7 to 20 carbon atoms, an alkylcarbonylamino group of 2 to 20 carbon atoms or an arylcarbonylamino group of 7 to 20 carbon atoms),
wherein the charge-transporting thin film-forming varnish further comprises a dopant.

2. The charge-transporting thin film-forming varnish of claim 1 , wherein the 2,2,6,6-tetraalkylpiperidine-N-oxyl derivative is 2,2,6,6-tetramethylpiperidine-N-oxyl.

3. The charge-transporting thin film-forming varnish of claim 1 or 2 , wherein the charge-transporting substance comprises a charge-transporting compound having a molecular weight of from 200 to 9,500.

4. The charge-transporting thin film-forming varnish of claim 1 , wherein the charge-transporting substance comprises at least one compound selected from the group consisting of arylamine derivatives and thiophene derivatives having a molecular weight of from 200 to 9,500.

5. The charge-transporting thin film-forming varnish of claim 1 , further comprising a fluorine atom-containing oligoaniline derivative.

6. The charge-transporting thin film-forming varnish of claim 5 , wherein the fluorine atom-containing oligoaniline derivative is a compound of formula (6)

(wherein R 301 is a hydrogen atom, an alkyl group of 1 to 20 carbon atoms which may be substituted with Z wherein Z is a hydrogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group or a carboxyl group, an aryl group of 6 to 20 carbon atoms which may be substituted with Z′ or a heteroaryl group of 2 to 20 carbon atoms which may be substituted with Z′ wherein Z′ is a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxyl group, a thiol group, a sulfonic acid group or a carboxyl group;
R 302 to R 310 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an alkyl group of 1 to 20 carbon atoms, alkenyl group of 2 to 20 carbon atoms, alkynyl group of 2 to 20 carbon atoms, aryl group of 6 to 20 carbon atoms or heteroaryl group of 2 to 20 carbon atoms which may be substituted with a halogen atom;
A is
a fluoroalkyl group of 1 to 20 carbon atoms, fluorocycloalkyl group of 3 to 20 carbon atoms, fluorobicycloalkyl group of 4 to 20 carbon atoms, fluoroalkenyl group of 2 to 20 carbon atoms or fluoroalkynyl group of 2 to 20 carbon atoms which may be substituted with a cyano group, a chlorine atom, a bromine atom, an iodine atom, a nitro group or a fluoroalkoxy group of 1 to 20 carbon atoms,
a fluoroaryl group of 6 to 20 carbon atoms which may be substituted with a cyano group, a chlorine atom, a bromine atom, an iodine atom, a nitro group, an alkyl group of 1 to 20 carbon atoms, a fluoroalkyl group of 1 to 20 carbon atoms or a fluoroalkoxy group of 1 to 20 carbon atoms,
an aryl group of 6 to 20 carbon atoms which is substituted with a fluoroalkyl group of 1 to 20 carbon atoms, a fluorocycloalkyl group of 3 to 20 carbon atoms, a fluorobicycloalkyl group of 4 to 20 carbon atoms, a fluoroalkenyl group of 2 to 20 carbon atoms or a fluoroalkynyl group of 2 to 20 carbon atoms and may be substituted with a cyano group, a halogen atom or a fluoroalkoxy group of 1 to 20 carbon atoms,
a fluoroaralkyl group of 7 to 20 carbon atoms which may be substituted with a cyano group, a chlorine atom, a bromine atom, an iodine atom, a nitro group, a fluoroalkoxy group of 1 to 20 carbon atoms, a fluoroalkyl group of 1 to 20 carbon atoms, a fluorocycloalkyl group of 3 to 20 carbon atoms, a fluorobicycloalkyl group of 4 to 20 carbon atoms, a fluoroalkenyl group of 2 to 20 carbon atoms or a fluoroalkynyl group of 2 to 20 carbon atoms, or
an aralkyl group of 7 to 20 carbon atoms which is substituted with a fluoroalkyl group of 1 to 20 carbon atoms, a fluorocycloalkyl group of 3 to 20 carbon atoms, a fluorobicycloalkyl group of 4 to 20 carbon atoms, a fluoroalkenyl group of 2 to 20 carbon atoms or a fluoroalkynyl group of 2 to 20 carbon atoms and may be substituted with a cyano group, a halogen atom or a fluoroalkoxy group of 1 to 20 carbon atoms; and
n 1 is an integer from 1 to 20).

7. The charge-transporting thin film-forming varnish of claim 1 , wherein the dopant comprises an arylsulfonic acid.

8. A charge-transporting thin film produced using the charge-transporting thin film-forming varnish of claim 1 .

9. An organic electroluminescent device comprising the charge-transporting thin film of claim 8 .

10. A method for producing a charge-transporting thin film, characterized by using the charge-transporting thin film-forming varnish of claim 1 .

11. A method for manufacturing an organic electroluminescent device, characterized by using the charge-transporting thin film-forming varnish claim 1 .

12. The method of claim 11 , wherein the varnish is used for forming a hole injecting layer in said organic electroluminescent device.

13. A method for reducing the driving voltage of an organic electroluminescent device having a charge-transporting thin film produced using a charge-transporting thin film-forming varnish,
which method is characterized by using the charge-transporting thin film-forming varnish of claim 1 as said charge-transporting thin film-forming varnish.

14. A method for increasing the brightness of an organic electroluminescent device having a charge-transporting thin film produced using a charge-transporting thin film-forming varnish,
which method is characterized by using the charge-transporting thin film-forming varnish of claim 1 as said charge-transporting thin film-forming varnish.

15. A method for increasing the brightness longevity of an organic electroluminescent device having a charge-transporting thin film produced using a charge-transporting thin film-forming varnish,
which method is characterized by using the charge-transporting thin film-forming varnish of claim 1 as said charge-transporting thin film-forming varnish.

16. The charge-transporting thin film-forming varnish of claim 1 wherein R B is a hydrogen atom, a hydroxyl group, an amino group, a carboxyl group, a cyano group, an oxo group, an isocyanato group, or an alkoxy group of 1 to 20 carbon atoms.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Higashi Masayuki

Classifications

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09D181/00

  Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers · CPC title

• C08K5/42

  Sulfonic acids; Derivatives thereof · CPC title

• C08L79/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00 · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title