# US 8,568,965 B2 · Organic semiconducting material, and film, organic electronic device and infrared dye composition each including said material

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- Number: US 8,568,965 B2
- Document ID: US8568965B2
- Status: Granted
- Kind: B2
- Application number: 13/432,603
- Filed: 2012-03-28
- Published: 2012-07-19
- Granted: 2013-10-29
- Earliest claimed: 2007-08-23
- Assignees: FUJIFILM Corporation
- Applicants: Tetsu Kitamura; Masayuki Hayashi; Kimiatsu Nomura
- Inventors: Tetsu Kitamura; Masayuki Hayashi; Kimiatsu Nomura
- Web page: https://patentgrep.com/patent/US8568965B2

## CPC

- C09B 47/00: Porphines; Azaporphines {(non-dyeing compounds C07D487/22)}
- C09B 69/008: {Dyes containing a substituent, which contains a silicium atom}
- H10K 30/50: Photovoltaic [PV] devices
- H10K 85/311: {Phthalocyanine}
- H10K 85/324: {comprising aluminium, e.g. Alq3}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 2102/103: {comprising indium oxides, e.g. ITO}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- 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

An organic semiconducting material comprises a naphthalocyanine derivative represented by formula (1); wherein M represents Si, Ge or Sn, R1 to R3 represent substituents other than a hydrogen atom except that all of R1 to R3 are identical straight-chain alkyl groups, and R4 to R27 each independently represents a hydrogen atom or a substituent.

## Claims

### Claim 1

A film comprising a naphthalocyanine compound represented by formula (1):
wherein
M represents Si,
R1 to R3 each represents an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an amino group, an alkylamino group having 1 to 30 carbon atoms, or aniline group having 6 to 30 carbon atoms, and may be substituted, and
R4 to R27 each independently represents a hydrogen atom or a substituent,
wherein at least one of R1 to R3 is a branched alkyl group having 3 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 6 to 12 carbon atoms.

### Claim 2 (depends on 1)

The film according to claim 1, which is formed by a vacuum evaporation method.

### Claim 3 (depends on 1)

The film according to claim 1, which is formed by a solution coating method.

### Claim 4

An organic electronic device comprising a naphthalocyanine compound represented by formula (1):
wherein
M represents Si,
R1 to R3 each represents an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an amino group, an alkylamino group having 1 to 30 carbon atoms, or aniline group having 6 to 30 carbon atoms, and may be substituted, and
R4 to R27 each independently represents a hydrogen atom or a substituent,
wherein at least one of R1 to R3 is a branched alkyl group having 3 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 6 to 12 carbon atoms.

### Claim 5 (depends on 4)

The organic electronic device according to claim 4, which is an organic transistor.

### Claim 6 (depends on 4)

The organic electronic device according to claim 4, which is an organic photoelectric transducer.