# US 9,049,771 B2 · Charge-transporting material and charge-transporting varnish

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- Number: US 9,049,771 B2
- Document ID: US9049771B2
- Status: Granted
- Kind: B2
- Application number: 13/129,988
- Filed: 2009-11-18
- Published: 2011-09-15
- Granted: 2015-06-02
- Earliest claimed: 2008-11-19
- Assignees: Nissan Chemical Industries, Ltd.
- Applicants: Takuji Yoshimoto; Tomohisa Yamada
- Inventors: Takuji Yoshimoto; Tomohisa Yamada
- Web page: https://patentgrep.com/patent/US9049771B2

## CPC

- H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}
- C09K 11/06: containing organic luminescent materials
- H10K 50/14: Carrier transporting layers
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/114: {Poly-phenylenevinylene; Derivatives thereof}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/342: {comprising iridium}
- H10K 85/351: {Metal complexes comprising lanthanides or actinides, e.g. comprising europium}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

Disclosed is a charge-transporting material comprising a heteropoly acid compound such as phosphomolybdic acid as a charge-transporting substance. Also disclosed is a charge-transporting varnish comprising the charge-transporting material and an organic solvent, wherein the charge-transporting substance is dissolved in the organic solvent. It becomes possible to provide a charge-transporting material which comprises a substance having high solubility in an organic solvent, charge-transporting properties, and an ability to oxidize hole transport materials, and a charge-transporting varnish comprising the charge-transporting material.

## Claims

### Claim 1

A charge-transporting thin film produced from a charge-transporting varnish consisting of a charge-transporting material and an organic solvent,
wherein the charge-transporting material contains a heteropolyacid compound as a charge-transporting substance, and
the heteropolyacid compound is uniformly dissolved in the organic solvent,
wherein the organic solvent contains one or more good solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, N-cyclohexyl-2-pyrrolidinone, cyclohexanol, ethylene glycol, 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, o-cresol, m-cresol, p-cresol, methyl isopropyl ketone, diethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, cyclohexanone, ethyl n-amyl ketone, isopropanol, t-butanol, allyl alcohol, 2-methyl-2-butanol, isobutanol, 2-methyl-1-butanol, 1-pentanol, 2-methyl-1-pentanol, 2-ethylhexanol, 1-octanol, 1-methoxy-2-butanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, and triethylene glycol dimethyl ether, and
wherein the organic solvent further contains a high-viscosity solvent having a viscosity at 25° C. of 10 to 200 mPa·s.

### Claim 2 (depends on 1)

The charge-transporting thin film according to claim 1, wherein the heteropolyacid compound is phosphomolybdic acid.

### Claim 3 (depends on 1)

The charge-transporting thin film according to claim 1, wherein the high-viscosity solvent is one or more solvent selected from the group consisting of cyclohexanol, ethylene glycol, 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, o-cresol, m-cresol and p-cresol.

### Claim 4 (depends on 1)

A layered product comprising a substrate and a charge-transporting thin film of claim 1 formed thereon.

### Claim 5 (depends on 4)

The layered product according to claim 4, wherein the substrate is an electrode substrate.

### Claim 6 (depends on 1)

The charge-transporting thin film of claim 1, wherein the thin film has a thickness of 0.1-200 nm.

### Claim 7 (depends on 1)

The charge-transporting thin film of claim 1, wherein the charge-transporting thin film has a conductivity of not less than 10−7S/cm.