# US 11,309,493 B2 · Formulations with a low particle content

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- Number: US 11,309,493 B2
- Document ID: US11309493B2
- Status: Granted
- Kind: B2
- Application number: 17/138,134
- Filed: 2020-12-30
- Published: 2021-04-22
- Granted: 2022-04-19
- Earliest claimed: 2015-01-30
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH; Seiko Epson Corporation
- Inventors: Edgar Boehm; Anja Gerhard; Dietmar Kunkel; Volker Hilarius; Masahiro Uchida; Takuya Sonoyama; Shuichi Takei; Koji Imamura
- Web page: https://patentgrep.com/patent/US11309493B2

## CPC

- H10K 71/311: {Purifying organic semiconductor materials}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 5/24: Electrically-conducting paints {(conductive materials H01B1/00)}
- C09D 7/20: Diluents or solvents
- C09D 11/033: characterised by the solvent
- C09D 11/037: characterised by the pigment
- C09D 11/10: based on artificial resins
- C09D 11/36: based on non-aqueous solvents
- C09D 11/52: Electrically conductive inks
- H01B 1/12: organic substances {(organic macromolecular compounds or compositions C08)}
- H10K 71/135: {using ink-jet printing}
- H10K 71/15: characterised by the solvent used
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/215: {comprising substituents, e.g. PCBM}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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)
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to formulations comprising at least one organic semiconductor and at least one organic solvent, characterized in that the formulation contains less than 10,000 particles per liter formulation having an average size in the range from 0.1 to 20 μm, to their use for the preparation of electronic devices, to methods for preparing electronic devices using the formulations of the present invention, and to electronic devices prepared from such methods and formulations.

## Claims

### Claim 1

A formulation comprising one or more organic semiconducting materials and one or more organic solvents, wherein the formulation contains less than 10,000 particles per liter formulation having an average particle size in the range from 0.1 to 20 μm, wherein the organic semiconducting material is a polymer having a molecular weight Mw of >5,000 g/mol.

### Claim 2 (depends on 1)

The formulation according to claim 1, wherein the formulation-contains less than 1,000 particles per liter formulation having an average particle size in the range from 0.2 to 20 μm.

### Claim 3 (depends on 1)

The formulation according to claim 1, wherein the formulation contains less than 100 particles per liter formulation having an average particle size in the range from 0.5 to 20 μm.

### Claim 4 (depends on 1)

The formulation according to claim 1, wherein the formulation-contains less than 10 metallic and/or electronically conducting particles per liter formulation having an average particle size in the range from 0.1 to 20 μm.

### Claim 5 (depends on 1)

The formulation according to claim 1, wherein the organic semiconducting material is selected from the group consisting of a hole injecting, hole transporting, electron blocking, light emitting, hole blocking, electron transporting, electron injecting and dielectric absorber material.

### Claim 6 (depends on 1)

The formulation according to claim 1, wherein the formulation contains one solvent.

### Claim 7 (depends on 1)

The formulation according to claim 1, wherein the formulation contains at least two different solvents, wherein the difference of the boiling points of two solvents of the at least two different solvents is ≥10° C.

### Claim 8 (depends on 7)

Formulation according to claim 7, wherein the solvent has a boiling point of ≥90° C.

### Claim 9 (depends on 1)

The formulation according to claim 1, wherein the formulation contains at least two different solvents, wherein the difference of the vapour pressure of two solvents of the at least two different solvents is ≥ a factor of 2.

### Claim 10 (depends on 1)

The formulation according to claim 1, wherein the formulation has a viscosity in the range of 1.5 to 100 mPas.

### Claim 11 (depends on 1)

The formulation according to claim 1, wherein the formulation contains additives and/or auxiliaries.

### Claim 12 (depends on 1)

A method for the preparation of a formulation according to claim 1, comprising dissolving the one or more organic semiconducting materials in one or more organic solvents and thereafter filtering the formulation using one or more membrane filters, having a pore size of ≤2 μm.

### Claim 13 (depends on 12)

The formulation according to claim 12, wherein the formulation contains as an additive at least one polymeric binder.

### Claim 14 (depends on 12)

The method according to claim 12, wherein the formulation is filtered by passing the membrane filter more than once, preferably more than 3 times, more preferably more than 10 times and most preferably more than 100 times.

### Claim 15 (depends on 1)

The method for the preparation of at least one layer of an electronic device, wherein the at least one layer is prepared by dip coating, spin coating, ink jet printing, nozzle printing, letter-press printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse-roller printing, offset lithography printing, flexographic printing, web printing, spray coating, curtain coating, brush coating, airbrush coating, slot dye coating or pad printing using the formulation according to claim 1.

### Claim 16 (depends on 15)

The method according to claim 15, wherein the electronic device is selected from the group consisting of an OLED, an OTFT, an OFET, a solar cell, a sensor, an organic diode and a RFID.

### Claim 17 (depends on 1)

A method comprising utilizing the formulation according to claim 1, for the preparation of at least one layer of an electronic device.

### Claim 18 (depends on 17)

The method according to claim 17, wherein the electronic device is selected from the group consisting of an OLED, an OTFT, an OFET, a solar cell, a sensor, an organic diode and a RFID.