Charge-transporting varnish

Patent metadata

Field	Value
Publication number	US-10090477-B2
Application number	US-201515313399-A
Country	US
Kind code	B2
Filing date	May 20, 2015
Priority date	May 23, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

A thin film that has high flatness and high charge transport properties and enables an organic EL element to achieve excellent luminance characteristics if applied thereto can be obtained by using a charge-transporting varnish which contains a charge-transporting substance, an organosilane compound that is composed of a polymer prepared in advance by subjecting an alkoxysilane compound to hydrolysis-condensation and having a weight average molecular weight of 500-10,000, and an organic solvent, said alkoxysilane compound containing at least one compound selected from among alkoxysilane compounds represented by formulae (1-1) and (1-2). SiR 1 (OR 2 ) 3 (1-1) SiR 1 2(OR 2 ) 2 (1-2) (In the formulae, each R 1 independently represents an alkyl group having 1-20 carbon atoms, which is substituted by Z 1 , or the like; each R 2 independently represents an alkyl group having 1-20 carbon atoms, which may be substituted by Z 3 ; and each of Z 1 and Z 3 represents a halogen atom or the like.).

First claim

The invention claimed is:

1. A charge-transporting varnish comprising a charge-transporting substance, 1 to 20 wt %, based on the weight of the charge-transporting substance, of an organosiloxane compound, and an organic solvent, wherein the organosiloxane compound has a weight-average molecular weight of 500 to 10,000 and is prepared beforehand by hydrolytic condensation of at least one alkoxysilane compound selected from among alkoxysilane compounds of formulas (1-1) and (1-2)
SiR 1 (OR 2 ) 3   (1-1)

SiR 1 2 (OR 2 ) 2   (1-2)

wherein
each R 1 is independently an alkyl group of 1 to 20 carbon atoms that is substituted with Z 1 or an aryl group of 6 to 20 carbon atoms that is substituted with Z 2 ;
each R 2 is independently an alkyl group of 1 to 20 carbon atoms that may be substituted with Z 3 ;
Z 1 is a halogen atom, a cyano group, a nitro group, an alkoxy group of 1 to 20 carbon atoms that is substituted with Z 3 , an aryl group of 6 to 20 carbon atoms that is substituted with Z 3 , or a heteroaryl group of 2 to 20 carbon atoms that is substituted with Z 3 ;
Z 2 is a halogen atom, a cyano group, a nitro group, or an alkyl group of 1 to 20 carbon atoms that is substituted with Z 3 ; and
Z 3 is a halogen atom, a cyano group or a nitro group.

2. The charge-transporting varnish of claim 1 , wherein the alkoxysilane compound includes at least one compound selected from among alkoxysilane compounds of formulas (1-1) and (1-2) and at least one compound selected from among alkoxysilane compounds of formulas (2-1) to (2-3)
Si(OR 3 ) 4   (2-1)

SiR 4 2 (OR 3 ) 2   (2-2)

SiR 4 (OR 3 ) 3   (2-3)

wherein
each R 3 is independently an alkyl group of 1 to 20 carbon atoms that may be substituted with Z 3 ;
each R 4 is independently an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms that may be substituted with Z 4 , an alkynyl group of 2 to 20 carbon atoms that may be substituted with Z 4 , an aryl group of 6 to 20 carbon atoms, or a heteroaryl group of 2 to 20 carbon atoms that may be substituted with Z 5 ;
Z 3 is as defined above;
Z 4 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, an aryl group of 6 to 20 carbon atoms that may be substituted with Z 6 , or a heteroaryl group of 2 to 20 carbon atoms that may be substituted with Z 6 ;
Z 5 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, a thiol group, an alkyl group of 1 to 20 carbon atoms that may be substituted with Z 6 , an alkenyl group of 1 to 20 carbon atoms that may be substituted with Z 6 , or an alkynyl group of 1 to 20 carbon atoms that may be substituted with Z 6 ; and
Z 6 is a halogen atom, a nitro group, a cyano group, a hydroxyl group or a thiol group.

3. The charge-transporting varnish of claim 1 or 2 , wherein the alkoxysilane compound includes an alkoxysilane compound of formula (1-1) and an alkoxysilane compound of formula (2-1).

4. The charge-transporting varnish of claim 1 , wherein the charge-transporting substance is an aniline derivative.

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

6. An organic electroluminescent device comprising the charge-transporting thin-film of claim 5 .

7. The organic electroluminescent device of claim 6 , wherein the charge-transporting thin-film is a hole injection layer or a hole-transporting layer.

8. The organic electroluminescent device of claim 6 , wherein the charge-transporting thin-film is a hole-transporting layer.

9. A method of fabricating an organic electroluminescent device, which method comprises the steps of
applying the charge-transporting varnish of claim 1 onto an anode substrate or a hole injection layer formed on the anode substrate, and
evaporating off the solvent to form a hole-transporting layer.

10. A method of producing a charge-transporting thin-film, which method is characterized by the steps of applying the charge-transporting varnish of claim 1 onto a substrate, and evaporating off the solvent.

11. A method of deepening the ionization potential of a charge-transporting thin-film obtained from a charge-transporting varnish containing a charge-transporting substance and an organic solvent, which method comprises the steps of, first,
preparing a polymer that has a weight-average molecular weight of 500 to 10,000 by hydrolytic condensation of at least one alkoxysilane compound selected from among alkoxysilane compounds of formulas (1-1) and (1-2)
SiR 1 (OR 2 ) 3   (1-1)

SiR 1 2 (OR 2 ) 2   (1-2)

wherein each R 1 is independently an alkyl group of 1 to 20 carbon atoms that is substituted with Z 1 or an aryl group of 6 to 20 carbon atoms that is substituted with Z 2 ; each R 2 is independently an alkyl group of 1 to 20 carbon atoms that may be substituted with Z 3 ; Z 1 is a halogen atom, a cyano group, a nitro group, an alkoxy group of 1 to 20 carbon atoms that is substituted with Z 3 , an aryl group of 6 to 20 carbon atoms that is substituted with Z 3 , or a heteroaryl group of 2 to 20 carbon atoms that is substituted with Z 3 ; Z 2 is a halogen atom, a cyano group, a nitro group, or an alkyl group of 1 to 20 carbon atoms that is substituted with Z 3 ; and Z 3 is a halogen atom, a cyano group or a nitro group and, subsequently,
adding said polymer to the charge-transporting varnish.

12. A method of deepening the ionization potential of a charge-transporting thin-film containing a charge-transporting substance, which method comprises the steps of, first,
preparing a polymer that has a weight-average molecular weight of 500 to 10,000 by hydrolytic condensation of at least one alkoxysilane compound selected from among alkoxysilane compounds of formulas (1-1) and (1-2) below into the charge-transporting thin-film together with the charge-transporting substance
SiR 1 (OR 2 ) 3   (1-1)

SiR 1 2 (OR 2 ) 2   (1-2)

wherein each R 1 is independently an alkyl group of 1 to 20 carbon atoms that is substituted with Z 1 or an aryl group of 6 to 20 carbon atoms that is substituted with Z 2 ; each R 2 is independently an alkyl group of 1 to 20 carbon atoms that may be substituted with Z 3 ; Z 1 is a halogen atom, a cyano group, a nitro group, an alkoxy group of 1 to 20 carbon atoms that is substituted with Z 3 , an aryl group of 6 to 20 carbon atoms that is substituted with Z 3 , or a heteroaryl group of 2 to 20 carbon atoms that is substituted with Z 3 ; Z 2 is a halogen atom, a cyano group, a nitro group, or an alkyl group of 1 to 20 carbon atoms that is substituted with Z 3 ; and Z 3 is a halogen atom, a cyano group or a nitro group and, subsequently,
introducing said polymer into the charge-transporting thin-film, together with the charge-transporting substance, during formation of the charge-transporting thin-film.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nakaie Naoki
• Hashimoto Jun
• Koga Haruka

Classifications

• C09D5/24

  Electrically-conducting paints {(conductive materials H01B1/00)} · CPC title

• C09D179/02

  Polyamines · CPC title

• C09D165/00

  Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers · CPC title

• H01L51/5088

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic