# US 2014/0190566 A1 · Organic photoelectric conversion element and organic solar cell using the same

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- Number: US 2014/0190566 A1
- Document ID: US20140190566A1
- Status: Published application
- Kind: A1
- Application number: 14/237,850
- Filed: 2012-08-06
- Published: 2014-07-10
- Earliest claimed: 2011-08-09
- Assignees: Konica Minolta, Inc.
- Inventors: Hiroaki Itoh
- Web page: https://patentgrep.com/patent/US20140190566A1

## CPC

- C07D 311/74: Benzo[b]pyrans, hydrogenated in the carbocyclic ring
- C07D 277/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 295/08: substituted by singly bound oxygen or sulfur atoms
- C07D 307/80: Radicals substituted by oxygen atoms
- C07D 493/10: Spiro-condensed systems
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 30/50: Photovoltaic [PV] devices
- H10K 85/146: {poly N-vinylcarbazol; Derivatives thereof}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

To provide an organic photoelectric conversion element whereby conversion efficiency is increased by morphology improvement in a power generation layer, and whereby short circuit current (Jsc) attenuation when irradiating light is simultaneously suppressed, and an organic solar cell using the same. An organic photoelectric conversion element having: a transparent first electrode; a power generation layer having a p-type organic semiconductor material and an n-type organic semiconductor material; and a second electrode, on a transparent substrate, in which the power generation layer is a bulk heterojunction power generation layer including the p-type organic semiconductor material and the n-type organic semiconductor material, and additionally includes a compound represented by either the following general formula (I) or general formula (II).

## Claims

### Claim at position 1

1-4. (canceled)

### Claim 5

An organic photoelectric conversion element comprising:
a transparent first electrode;
a power generation layer having a p-type organic semiconductor material and an n-type organic semiconductor material; and
a second electrode, on a transparent substrate,
wherein the power generation layer is a bulk heterojunction power generation layer including the p-type organic semiconductor material and the n-type organic semiconductor material, and additionally comprises a compound represented by either general formula (I) or general formula (II) shown below:
wherein R1 represents a substituted or unsubstituted aryl group, Z1 and Z2 each represents a substituted or unsubstituted alkylene group having 1 to 3 carbon atoms, provided that sum of the carbon atoms in the alkylene group represented by Z1 and Z2 is 3 to 6; A represents an oxygen atom, N—Z3, or S(O)n5, and Z3 represents an alkyl group or an aryl group; n5 represents an integer of from 0 to 2;
wherein R4 represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted trialkylsilyl group, R5, R6, R7, R8 and R9 each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkenyloxy group, a substituted or unsubstituted acylamino group, halogen atom, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted acyloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted sulfonamide group, a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted heterocyclic ring, a substituted or unsubstituted fused ring, or a combination thereof; two groups among R4 to R9 may be linked to each other to form a substituted or unsubstituted 5- to 6-membered ring.

### Claim 6 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein the general formula (I) is represented by any one of the following general formulas (I-A) to (I-E):
wherein R2 and R3 represent a halogen atom, a substituted or unsubstituted alkyl group (—Ra) a hydroxyalkyl group (—Ra(OH)), an alkoxy group (—ORa), an aryloxy group, an amino group (—NH2, —NHRa, —N(Ra)2), a thioether group (—SRa), an ester group, —CORa, —COORa, —NHCORa, —NHCOORa, —NHSO2Ra, or an alkylcarbonyloxy group (—OCORa), in which Ra represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and m5 and l5 represent an integer of from 0 to 4.

### Claim 7 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein the general formula (II) is represented by the following general formula (II-A):
in general formula (II-A), R10 to R13 each independently represents a hydrogen atom or a substituted or unsubstituted alkyl group, in which R11 and R13 may be linked to each other to form a substituted or unsubstituted 5- to 6-membered ring.

### Claim 8 (depends on 6)

The organic photoelectric conversion element according to claim 6, wherein the power generation layer comprises at least one of the compounds represented by any one of the general formulas (I-A) to (I-E) shown above.

### Claim 9 (depends on 7)

The organic photoelectric conversion element according to claim 7, wherein the power generation layer comprises the compounds represented by the general formula (II-A) shown above.

### Claim 10 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein the compound represented by either general formula (I) or general formula (II) shown above is comprised in a range of 0.1 to 15 parts by mass with respect to 100 parts by mass of sum of the p-type semiconductor and n-type semiconductor.

### Claim 11 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein solubility parameter (SP value) of the compound represented by either general formula (I) or general formula (II) shown above is from 19 to 23.

### Claim 12 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein the power generation layer comprises the compound represented by general formula (I) shown above.

### Claim 13 (depends on 5)

The organic photoelectric conversion element according to claim 5, wherein the power generation layer comprises the compound represented by general formula (II) shown above.

### Claim 14 (depends on 5)

An organic solar cell comprising the organic photoelectric conversion element set forth in claim 5.