Charge-transporting varnish

Patent metadata

Field	Value
Publication number	US-10069075-B2
Application number	US-201414770305-A
Country	US
Kind code	B2
Filing date	Feb 18, 2014
Priority date	Feb 26, 2013
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

A charge-transporting varnish including charge-transporting material comprising N,N′-diaryl benzidine derivatives represented by formula (1), a charge-accepting dopant comprising heteropoly acid, and an organic solvent.

[In the formula, R 1 to R 8 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms or an alkynyl having 2 to 20 carbon atoms; and Ar 1 and Ar 2 independently represent groups represented by formulas (2) or (3).

(In the formula, R 9 to R 18 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms or an alkynyl having 2 to 20 carbon atoms; and X 1 and X 2 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, diphenylamino, 1-naphthylphenylamino, 2-naphthylphenylamino, di(1-naphthyl)-amino, and di(2-naphthyl)-amino or 1-naphthyl-2-naphtylamino.)]

First claim

The invention claimed is:

1. A charge-transporting varnish comprising a charge-transporting material consisting of an N,N′-diarylbenzidine derivative of formula (1), a charge-accepting dopant consisting of a heteropolyacid, and a solvent consisting of at least one organic solvent:

wherein R 1 to R 8 are each independently a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbons, an alkenyl group of 2 to 20 carbons or an alkynyl group of 2 to 20 carbons; and Ar 1 and Ar 2 are each independently a group of formula (2) or (3):

wherein R 9 to R 18 are each independently a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbons, an alkenyl group of 2 to 20 carbons or an alkynyl group of 2 to 20 carbons; and X 1 and X 2 are each independently a hydrogen atom, a halogen atom, an alkyl group of 1 to 20 carbons, an alkenyl group of 2 to 20 carbons, an alkynyl group of 1 to 20 carbons, a diphenylamino group, a 1-naphthylphenylamino group, a 2-naphthylphenylamino group, a di(1-naphthyl)amino group, a di(2-naphthyl)amino group or a 1-naphthyl-2-naphthylamino group.

2. The charge-transporting varnish according to claim 1 , wherein R 1 to R 8 are hydrogen atoms, fluorine atoms or alkyl groups of 1 to 20 carbons.

3. The charge-transporting varnish according to claim 1 or 2 , wherein R 9 to R 18 are hydrogen atoms, fluorine atoms or alkyl groups of 1 to 20 carbons.

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

5. An electronic device comprising the charge-transporting thin-film of claim 4 .

6. An organic electroluminescence device comprising the charge-transporting thin-film of claim 4 .

7. The organic electroluminescence device according to claim 6 , wherein the charge-transporting thin-film is a hole injection layer or a hole transport layer.

8. The charge-transporting varnish according to claim 1 , wherein the organic solvent comprises (i) a high-solvency solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, diethylene glycol monomethyl ether, and mixtures thereof, and optionally comprises (ii) a high-viscosity organic solvent selected from the group consisting of cyclohexanol, ethylene glycol, ethylene glycol diglycidyl ether, 1,3 octylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, 1,3-butanediol, 2,3 butanediol, 1,4-butanediol, propylene glycol, hexylene glycol, and mixtures thereof and/or (iii) a solvent selected from the group consisting of ethylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether, diacetone alcohol, γ-butyrolactone, ethyl lactate, n-hexyl acetate, and mixtures thereof.

Assignees

• Nissan Chemical Ind Ltd

Inventors

• Nakaie Naoki
• Takayama Yuki

Classifications

• H01L2251/303

  Electricity · mapped topic

• H01L51/0059 Primary

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic

• H01L51/5088

  Electricity · mapped topic

• H01L2251/556

  Electricity · mapped topic