# US 10,770,659 B2 · Composition for hole trapping layer of organic photoelectric conversion element

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- Number: US 10,770,659 B2
- Document ID: US10770659B2
- Status: Granted
- Kind: B2
- Application number: 15/770,305
- Filed: 2016-10-21
- Published: 2018-11-01
- Granted: 2020-09-08
- Earliest claimed: 2015-11-06
- Assignees: Nissan Chemical Industries, Ltd.
- Applicants: Nissan Chemical Industries, Ltd.
- Inventors: Takuji Yoshimoto; Juro Oshima; Shun Sugawara
- Web page: https://patentgrep.com/patent/US10770659B2

## CPC

- C08G 73/0266: {Polyanilines or derivatives thereof}
- C08G 73/02: Polyamines
- H10K 30/82: Transparent electrodes, e.g. indium tin oxide [ITO] electrodes
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- H01B 1/124: {Intrinsically conductive polymers}
- H10K 30/20: comprising organic-organic junctions, e.g. donor-acceptor junctions
- H10K 30/353: {comprising blocking layers, e.g. exciton blocking layers}
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/549: Organic PV cells
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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

Provided is a composition for a hole trapping layer of an organic photoelectric conversion element, such composition: containing a solvent and a charge-transporting substance comprising a polyaniline derivative represented by formula (1); and providing a thin film that is suitable as a hole trapping layer of an organic photoelectric conversion element and can also be used to produce an inverse lamination type organic photoelectric conversion element. {R1-R6 each independently denote a hydrogen atom or the like, but one of the R1-R4 groups is a sulfonic acid group, one or more of the other R1-R4 groups is an alkoxy group having 1-20 carbon atoms, a thioalkoxy group having 1-20 carbon atoms, an alkyl group having 1-20 carbon atoms, an alkenyl group having 2-20 carbon atoms, an alkynyl group having 2-20 carbon atoms, a haloalkyl group having 1-20 carbon atoms, an aryl group having 6-20 carbon atoms or an aralkyl group having 7-20 carbon atoms, and m and n are numbers that satisfy the relationships 0≤m≤1, 0≤n≤1 and m+n=1.}

## Claims

### Claim 1

A composition for a hole-collecting layer in an organic photoelectric conversion device, the composition comprising a charge-transporting substance consisting of a polyaniline derivative of formula (1):
wherein R1 to R4 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group of 1 to 20 carbon atoms, a thioalkoxy group of 1 to 20 carbon atoms, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, a haloalkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an aralkyl group of 7 to 20 carbon atoms or an acyl group of 1 to 20 carbon atoms, with one of the R1 to R4 moieties being a sulfonic acid group and a single one of the remaining R1 to R4 moieties being an alkoxy group of 1 to 10 carbon atoms, R5 and R6 are a hydrogen atom, and m and n are each numbers which satisfy the conditions 0≤m≤1, 0≤n≤1 and m+n =1, and a solvent.

### Claim 2 (depends on 1)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1, wherein R1 is a sulfonic acid group and R4 is an alkoxy group of 1 to 20 carbon atoms.

### Claim 3 (depends on 1, 2)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1 or 2, further comprising an electron-accepting dopant substance that differs from the polyaniline derivative of formula (1).

### Claim 4 (depends on 3)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 3, wherein the electron-accepting dopant substance is a Brønsted acid.

### Claim 5 (depends on 3)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 3, wherein the electron-accepting dopant substance is an arylsulfonic acid compound of formula (2):
wherein X represents oxygen; A is a naphthalene ring or an anthracene ring; B is a divalent to tetravalent perfluorobiphenyl group; the letter l is an integer that represents the number of sulfonic acid groups bonded to A and satisfies the condition l≤1≤4; and q is an integer that represents the number of bonds between B and X and is from 2 to 4, naphthalenetrisulfonic acid or polystyrenesulfonic acid.

### Claim 6 (depends on 1)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1, further comprising an alkoxysilane.

### Claim 7 (depends on 1)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1, wherein the organic photoelectric conversion device is an organic thin-film solar cell or a photosensor.

### Claim 8 (depends on 1)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1, wherein the solvent includes a high-viscosity solvent having a viscosity at 25° C. of from 10 to 500 mPa·s.

### Claim 9 (depends on 1)

The composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1, wherein the solvent consists of one or more solvent selected from alcohol solvents and water.

### Claim 10 (depends on 1)

A hole-collecting layer obtained using the composition for a hole-collecting layer in an organic photoelectric conversion device according to claim 1.

### Claim 11 (depends on 10)

An organic photoelectric conversion device comprising the hole-collecting layer of claim 10 and an active layer provided so as to be in contact therewith.

### Claim 12 (depends on 11)

The organic photoelectric conversion device of claim 11, wherein the ionizing potential of the hole-collecting layer and the ionizing potential of a p-type semiconductor included in the active layer have a difference therebetween of not more than 0.2 eV.

### Claim 13 (depends on 11, 12)

The organic photoelectric conversion device of claim 11 or 12, wherein the active layer includes a fullerene derivative.

### Claim 14 (depends on 11, 12)

The organic photoelectric conversion device of claim 11 or 12, wherein the active layer includes a polymer having a thiophene skeleton on the main chain.

### Claim 15 (depends on 11, 12)

The organic photoelectric conversion device of claim 11 or 12, wherein the active layer includes a fullerene derivative and a polymer having a thiophene skeleton on the main chain.

### Claim 16 (depends on 11)

The organic photoelectric conversion device of claim 11 which is an inverted stack structure-type device.

### Claim 17 (depends on 11)

The organic photoelectric conversion device of claim 11 which is an organic thin-film solar cell or a photosensor.

### Claim 18

A charge-transporting composition comprising a charge-transporting substance consisting of a polyaniline derivative of formula (1):
wherein R1 to R4 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a sulfonic acid group, an alkoxy group of 1 to 20 carbon atoms, a thioalkoxy group of 1 to 20 carbon atoms, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 20 carbon atoms, an alkynyl group of 2 to 20 carbon atoms, a haloalkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, an aralkyl group of 7 to 20 carbon atoms or an acyl group of 1 to 20 carbon atoms, with one of the R1 to R4 moieties being a sulfonic acid group and a single one of the remaining R1 to R4 moieties being an alkoxy group of 1 to 10 carbon atoms, R5 and R6 are a hydrogen atom, and m and n are each numbers which satisfy the conditions 0 ≤m 1, 0 ≤n≤1 and m+n=1, an electron-accepting dopant substance differing from the polyaniline derivative of formula (1), and a solvent.

### Claim 19 (depends on 18)

The charge-transporting composition of claim 18 which further comprises an alkoxysilane.

### Claim 20 (depends on 18, 19)

The charge-transporting composition of claim 18 or 19, wherein the electron-accepting dopant substance is an arylsulfonic acid compound of formula (2):
wherein X represents oxygen, A is a naphthalene ring or an anthracene ring, B is a divalent to tetravalent perfluorobiphenyl group, the letter l is an integer that represents the number of sulfonic acid groups bonded to A and satisfies the condition l≤1≤4, and q is an integer that represents the number of bonds between B and X and is from 2 to 4, naphthalenetrisulfonic acid or polystyrenesulfonic acid.