# US 8,772,763 B2 · Photovoltaic cell

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- Number: US 8,772,763 B2
- Document ID: US8772763B2
- Status: Granted
- Kind: B2
- Application number: 13/502,639
- Filed: 2010-10-29
- Published: 2012-08-16
- Granted: 2014-07-08
- Earliest claimed: 2009-10-29
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Ken Yoshimura; Katsuhiro Suenobu
- Inventors: Ken Yoshimura; Katsuhiro Suenobu
- Web page: https://patentgrep.com/patent/US8772763B2

## CPC

- C08G 61/123: {derived from five-membered heterocyclic compounds}
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- G16Z 99/00: Subject matter not provided for in other main groups of this subclass
- H10K 30/30: comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/344: containing heteroatoms
- C08G 2261/364: containing hetero atoms
- C08G 2261/411: Suzuki reactions
- C08G 2261/91: Photovoltaic applications
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 85/151: {Copolymers}
- H10K 85/211: {Fullerenes, e.g. C60}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- G16Z: INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR SPECIFIC APPLICATION FIELDS, NOT OTHERWISE PROVIDED FOR
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention provides a photovoltaic cell having a large short-circuit current density and a large photoelectric conversion efficiency. This photovoltaic cell comprises: a first electrode; a second electrode; an active layer between the first electrode and the second electrode; wherein the active layer contains a macromolecular compound having a structural unit represented by Formula (1): wherein Ar1 and Ar2 are the same as or different from each other and represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group; X1 and X2 are the same as or different from each other and represent —O—, —S—, —C(═O)—, —S(═O)—, —SO2—, —C(R50)(R51)—, —Si(R3)(R4)—, —N(R5)—, —B(R6)—, —P(R7)—, or —P(═O)(R8)—; R50, R51, R3, R4, R5, R6, R7, and R8 are the same as or different from each other and represent a hydrogen atom, a halogen atom, or a monovalent organic group; and X1 and Ar2 are bonded with atoms adjacent to each other on a ring that constitutes Ar1, and X2 and Ar1 are bonded with atoms adjacent to each other on a ring that constitutes Ar2, wherein an inverse of the excitation energy of the macromolecular compound from a ground singlet state to a lowest excited singlet state that is calculated using the time-dependent density functional theory is 0.43 (eV−1) or more.

## Claims

### Claim 1

A photovoltaic cell comprising:
a first electrode;
a second electrode; and
an active layer positioned between the first electrode and the second electrode;
wherein the active layer contains a macromolecular compound having a structural unit represented by Formula (1) or Formula (2):
wherein R50 and R51 are the same as or different from each other and represent a hydrogen atom, a halogen atom, or a monovalent organic group,
and further having a structural unit represented by Formula (3) or Formula (4):
wherein Rs are the same as or different from each other and represent a hydrogen atom or a substituent, or are bonded with each other to form a ring, wherein the substituent is selected from a group consisting of an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an acyl group, an acyloxy group, an amido group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, a nitro group, and a cyano group, wherein a hydrogen atom contained in the substituent is optionally substituted with a fluorine atom,
wherein an inverse of excitation energy of the macromolecular compound from a ground singlet state to a lowest excited singlet state that is calculated using a time-dependent density functional theory is 0.43 (eV−1) or more.

### Claim 2 (depends on 1)

The photovoltaic cell according to claim 1, wherein the inverse of the excitation energy of the macromolecular compound from the ground singlet state to the lowest excited singlet state is 0.45 (eV−1) or more.

### Claim 3 (depends on 1)

The photovoltaic cell according to claim 1, wherein the monovalent organic group is an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an acyl group, an acyloxy group, an amido group, an acid imido group, an amino group, a substituted amino group, a substituted silyl group, a substituted silyloxy group, a substituted silylthio group, a substituted silylamino group, a monovalent heterocyclic group, a heterocyclyloxy group, a heterocyclylthio group, an arylalkenyl group, an arylalkynyl group, a carboxyl group, or a cyano group.

### Claim 4 (depends on 1)

A solar cell module comprising the photovoltaic cell according to claim 1.

### Claim 5 (depends on 1)

An image sensor comprising the photovoltaic cell according to claim 1.

### Claim 6

An organic thin film transistor comprising:
a gate electrode;
a source electrode;
a drain electrode; and
an active layer;
wherein the active layer contains a macromolecular compound having a structural unit represented by Formula (1) or Formula (2):
wherein R50 and R51 are the same as or different from each other and represent a hydrogen atom, a halogen atom, or a monovalent organic group,
and further having a structural unit represented by Formula (3) or Formula (4):
wherein Rs are the same as or different from each other and represent a hydrogen atom or a substituent, or are bonded with each other to form a ring, wherein the substituent is selected from a group consisting of an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkyloxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an acyl group, an acyloxy group, an amido group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, a nitro group, and a cyano group, wherein a hydrogen atom contained in the substituent is optionally substituted with a fluorine atom,
wherein an inverse of excitation energy of the macromolecular compound from a ground singlet state to a lowest excited singlet state that is calculated using a time-dependent density functional theory is 0.43 (eV−1) or more.

### Claim 7

A method of calculating excitation energy of a macromolecular compound comprising a repeated unit represented by Formula (2) from a ground singlet state to a lowest excited singlet state, the method comprising:
calculating, using a processor, excitation energy of a compound represented by Formula (2-1), excitation energy of a compound represented by Formula (2-2), and excitation energy of a compound represented by Formula (2-3) by a time-dependent density functional theory;
plotting, on a coordinate plane in which a value represented by 1/k is assigned on an abscissa axis when number of aromatic rings contained in a main chain of the compound is assumed to be k and excitation energy is assigned on an ordinate axis, a first point of which abscissa is a value represented by 1/k for the compound represented by Formula (2-1) and of which ordinate is the excitation energy of the compound represented by Formula (2-1), a second point of which abscissa is a value represented by 1/k for the compound represented by Formula (2-2) and of which ordinate is the excitation energy of the compound represented by Formula (2-2), and a third point of which abscissa is a value represented by 1/k for the compound represented by Formula (2-3) and of which ordinate is the excitation energy of the compound represented by Formula (2-3);
calculating an approximate straight line that connects the first point, the second point, and the third point by least-squares method; and
calculating an ordinate of an intersection point of a straight line on which the value represented by 1/k is 0 with the approximate straight line on the coordinate plane, as the excitation energy of the macromolecular compound;
wherein Formulae (2), (2-1), (2-2) and (2-3) are as follows:
—Ar3— (2)
H—Ar3—H (2-1)
H—Ar3—Ar3—H (2-2)
H—Ar3—Ar3—Ar3—H (2-3)
wherein Formula (2) represents a divalent organic group comprising one or a plurality of structure units represented by Formula (1); wherein H represents a hydrogen atom; and when Ar3 is plurally present, Ar3s may be the same as or different from each other,
wherein Formula (1) is as follows:
wherein Ar1 and Ar2 are the same as or different from each other and represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group; X1 and X2 are the same as or different from each other and represent —O—, —S—, —C(═O)—, —S(═O)—, —SO2—, —C(R50)(R51)—, —Si(R3)(R4)—, —N(R5)—, —B(R6)—, —P(R7)—, or —P(═O)(R8)—; R50, R51, R3, R4, R5, R6, R7, and R8 are the same as or different from each other and represent a hydrogen atom, a halogen atom, or a monovalent organic group; and X1 and Ar2 are bonded with atoms adjacent to each other on a ring that constitutes Ar1, and X2 and Ar1 are bonded with atoms adjacent to each other on a ring that constitutes Ar2.