# US 8,785,921 B2 · Device comprising positive hole injection transport layer, method for producing the same and ink for forming positive hole injection transport layer

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- Number: US 8,785,921 B2
- Document ID: US8785921B2
- Status: Granted
- Kind: B2
- Application number: 12/989,732
- Filed: 2009-04-28
- Published: 2011-07-07
- Granted: 2014-07-22
- Earliest claimed: 2008-04-28
- Assignees: Dai Nippon Printing Co., Ltd.
- Applicants: Shigehiro Ueno; Keisuke Hashimoto; Masato Okada; Seiji Take; Yosuke Taguchi; Masataka Kano; Shin-ya Fujimoto
- Inventors: Shigehiro Ueno; Keisuke Hashimoto; Masato Okada; Seiji Take; Yosuke Taguchi; Masataka Kano; Shin-ya Fujimoto
- Web page: https://patentgrep.com/patent/US8785921B2

## CPC

- H05B 33/10: Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
- C09D 11/52: Electrically conductive inks
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/828: Transparent cathodes, e.g. comprising thin metal layers
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- H10K 85/115: {Polyfluorene; Derivatives thereof}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 2102/331: {Nanoparticles used in non-emissive layers, e.g. in packaging layer}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A device capable of having an easy production process and achieving a long lifetime. The device has a substrate, two or more electrodes facing each other disposed on the substrate and a positive hole injection transport layer disposed between two electrodes among the two or more electrodes. The positive hole injection transport layer has a transition metal-containing nanoparticle containing at least a transition metal compound including a transition metal oxide, a transition metal and a protecting agent, or at least the transition metal compound including the transition metal oxide, and the protecting agent.

## Claims

### Claim 1

A device comprising a substrate, two or more electrodes facing each other disposed on the substrate and a positive hole injection transport layer disposed between two electrodes among the two or more electrodes, wherein the positive hole injection transport layer comprises a transition metal-containing nanoparticle containing at least a transition metal compound including a transition metal oxide, a transition metal and a protecting agent, or at least the transition metal compound including the transition metal oxide, and the protecting agent; wherein the protecting agent in the transition metal-containing nanoparticle contains at least one kind selected from the group consisting of an alkyl group, an aromatic hydrocarbon and a heterocyclic ring, and a linking group which functions to connect the transition metal and/or transition metal compound; and
wherein the linking group is one or more kinds selected from functional groups represented by the following formulae (1a) to (1l):
wherein each of Z1, Z2 and Z3 independently represents a halogen atom or an alkoxy group.

### Claim 2 (depends on 1)

The device according to claim 1, wherein the transition metal and the transition metal in the transition metal compound contained in the transition metal-containing nanoparticle are at least one kind of metal selected from the group consisting of molybdenum, tungsten, vanadium and rhenium.

### Claim 3 (depends on 1)

The device according to claim 1, wherein the positive hole injection transport layer comprises two or more kinds of the transition metal-containing nanoparticles which have different kinds of the transition metal respectively.

### Claim 4 (depends on 1)

The device according to claim 1, wherein an average particle diameter of the transition metal-containing nanoparticle is 15 nm or less.

### Claim 5 (depends on 1)

The device according to claim 1, wherein the positive hole injection transport layer comprises at least the transition metal-containing nanoparticle and a positive hole transport compound.

### Claim 6 (depends on 5)

The device according to claim 5,
wherein the positive hole transport compound has a moiety A having a sum atomic weight MA of 100 or more,
wherein the protecting agent in the transition metal-containing nanoparticle has, besides the linking group, a moiety B having a sum atomic weight MB of 100 or more,
the sum atomic weight MB and the sum atomic weight MA satisfy a relationship of the following formula (I):
|MA−MB|/MB≦2, and Formula (I)
the sum atomic weight MB is larger than one third of a molecular weight of the protecting agent, and
wherein a solubility parameter SA of the moiety A and a solubility parameter SB of the moiety B satisfy a relationship of the following formula (II):
|SA−SB|≦2. Formula (II)

### Claim 7 (depends on 6)

The device according to claim 6, wherein the moiety B has a same skeleton as that of the moiety A, or a similar skeleton containing a spacer structure in the same skeleton.

### Claim 8 (depends on 5)

The device according to claim 5, wherein the positive hole transport compound is a positive hole transport polymer compound.

### Claim 9 (depends on 1)

The device according to claim 1, wherein the positive hole injection transport layer comprises layers in which at least a layer containing the transition metal-containing nanoparticle and a layer containing the positive hole transport compound are laminated.

### Claim 10 (depends on 1)

The device according to claim 1, wherein the positive hole injection transport layer comprises the layers in which at least the layer containing the transition metal-containing nanoparticle and the layer containing at least the transition metal-containing nanoparticle and the positive hole transport compound are laminated.

### Claim 11 (depends on 1)

The device according to claim 1, wherein the protecting agent in the transition metal-containing nanoparticle contains a charge transport group.

### Claim 12 (depends on 1)

The device according to claim 1, wherein the device is an organic EL element comprising an organic layer containing at least a light emitting layer.

### Claim 13

A method for producing a device comprising a substrate, two or more electrodes facing each other disposed on the substrate and a positive hole injection transport layer disposed between two electrodes among the two or more electrodes comprising:
a preparation step of preparing an ink for forming a positive hole injection transport layer containing a transition metal-containing nanoparticle containing a transition metal and/or transition metal compound and a protecting agent, and an organic solvent;
a formation step of forming the positive hole injection transport layer on any of layers on the electrodes using the ink for forming the positive hole injection transport layer; and
an oxidation step of oxidizing at least a part of the transition metal and/or transition metal compound in the transition metal-containing nanoparticle to produce a transition metal oxide; wherein the protecting agent in the transition metal-containing nanoparticle contains at least one kind selected from the group consisting of an alkyl group, an aromatic hydrocarbon and a heterocyclic ring, and a linking group which functions to connect the transition metal and/or transition metal compound; and
wherein the linking group is one or more kinds selected from functional groups represented by the following formulae (1a) to (1l):
wherein each of Z1, Z2 and Z3 independently represents a halogen atom or an alkoxy group.

### Claim 14 (depends on 13)

The method for producing the device according to claim 13 comprising:
the formation step of forming the positive hole injection transport layer containing the transition metal-containing nanoparticle containing the transition metal and/or transition metal compound and the protecting agent on any of the layers on the electrodes; and
the oxidation step of oxidizing at least the part of the transition metal and/or transition metal compound in the transition metal-containing nanoparticle in the positive hole injection transport layer to produce the transition metal oxide.

### Claim 15 (depends on 13)

The method for producing the device according to claim 13, wherein the oxidation step is performed after preparing the ink for forming the positive hole injection transport layer before forming the positive hole injection transport layer so that the formation step is forming the positive hole injection transport layer using the oxidized ink for forming the positive hole injection transport layer.

### Claim 16 (depends on 13)

The method for producing the device according to claim 13, wherein the oxidation step is performed in the presence of oxygen.

### Claim 17 (depends on 13)

The method for producing the device according to claim 13, wherein the oxidation step includes a heating process.

### Claim 18 (depends on 13)

The method for producing the device according to claim 13, wherein the oxidation step includes a light irradiation process.

### Claim 19 (depends on 13)

The method for producing the device according to claim 13, wherein the oxidation step includes a process of using active oxygen.