# US 9,040,966 B2 · Method for producing organic transistor, organic transistor, method for producing semiconductor device, semiconductor device, and electronic apparatus

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- Number: US 9,040,966 B2
- Document ID: US9040966B2
- Status: Granted
- Kind: B2
- Application number: 13/981,721
- Filed: 2012-02-23
- Published: 2013-12-12
- Granted: 2015-05-26
- Earliest claimed: 2011-03-30
- Assignees: Sony Corporation
- Applicants: Norihito Kobayashi
- Inventors: Norihito Kobayashi
- Web page: https://patentgrep.com/patent/US9040966B2

## CPC

- H10K 85/60: Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence)
- C07D 493/06: Peri-condensed systems
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 10/471: {the gate dielectric comprising only organic materials}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided is a method of producing an organic transistor, including collectively forming a gate insulating film and an organic semiconductor film by applying, onto a gate electrode, a solution including a polymer and at least one of compounds represented by General Formulas 1 to 4 and 5 to 7, a compound having a structure represented by General Formula 4, a compound having a structure represented by General Formula 5 or 6, and forming a source electrode and a drain electrode on the organic semiconductor film. (where R is a linear or branched alkyl group) (where R is an alkyl group) (where R is an alkyl group) (where A1 and A2 are represented by Formula 8) (where R is an alkyl group or another substituent).

## Claims

### Claim 1

A method of producing an organic transistor, the method comprising:
collectively forming a gate insulating film and an organic semiconductor film by applying, onto a gate electrode disposed on a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
forming the gate insulating film and the organic semiconductor film on the gate insulating film by spontaneous phase separation; and
forming a source electrode and a drain electrode on the organic semiconductor film
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, and a number of R's is 2 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).

### Claim 2 (depends on 1)

The method according to claim 1, wherein the at least one compound is one compound represented by the following Formulas 9 to 17

### Claim 3 (depends on 1)

The method according to claim 1, wherein a solvent of the raw material solution is at least one of xylene, p-xylene, toluene, mesitylene, tetralin, anisole, benzene, 1,2-dichlorobenzene, o-dichlorobenzene, cyclohexane, and ethyl cyclohexane.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the gate insulating film and the organic semiconductor film are formed by forming an organic insulating film on the gate electrode, and applying the raw material solution onto the organic insulating film.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the polymer is at least one of poly(α-methylstyrene) and cycloolefin copolymer.

### Claim 6

An organic transistor comprising:
a gate insulating film and an organic semiconductor film collectively formed by applying, onto a gate electrode disposed on a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
the gate insulating film and the organic semiconductor film being formed on the gate insulating film by spontaneous phase separation; and
a source electrode and a drain electrode disposed on the organic semiconductor film
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, a number of R's is 2 to 5)
(where R is an alkyl group, a number of R's is 1 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).

### Claim 7 (depends on 6)

The organic transistor according to claim 6, wherein the gate insulating film and the organic semiconductor film are formed by forming an organic insulating film on the gate electrode, and applying the raw material solution onto the organic insulating film.

### Claim 8 (depends on 6)

The organic transistor according to claim 6, wherein the polymer is at least one of poly(α-methylstyrene) and cycloolefin copolymer.

### Claim 9

An electronic apparatus comprising:
an organic transistor which includes a gate insulating film and an organic semiconductor film collectively formed by applying, onto a gate electrode disposed on a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
the gate insulating film and the organic semiconductor film being formed on the gate insulating film by spontaneous phase separation, and
a source electrode and a drain electrode disposed on the organic semiconductor film
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, and a number of R's is 2 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where R is an alkyl group, a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).

### Claim 10

A method of producing a semiconductor device, the method comprising:
collectively forming a gate insulating film and an organic semiconductor film by applying, onto a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
the gate insulating film and the organic semiconductor film formed on the gate insulating film by spontaneous phase separation
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, a number of R's is 2 to 5)
(where R is an alkyl group, a number of R's is 1 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).

### Claim 11

A semiconductor device comprising:
a gate insulating film and an organic semiconductor film collectively formed by applying, onto a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
the gate insulating film and the organic semiconductor film being formed on the gate insulating film by spontaneous phase separation
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, a number of R's is 2 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where R is an alkyl group and a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).

### Claim 12

An electronic apparatus comprising:
a semiconductor device which includes a gate insulating film and an organic semiconductor film collectively formed by applying, onto a base substrate, a raw material solution, in a film shape, including a polymer and at least one compound of a compound represented by General Formula 1, a compound represented by General Formula 2, a compound represented by General Formula 3, a compound represented by General Formula 4, a compound having a structure represented by General Formula 4, in which R is a substituent other than an alkyl group, a compound represented by General Formula 5, a compound represented by General Formula 6, a compound having a structure represented by General Formula 5 or 6, in which R is a substituent other than an alkyl group, and a compound represented by General Formula 7,
the gate insulating film and the organic semiconductor film formed on the insulating film by spontaneous phase separation
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is a linear or branched alkyl group)
(where R is an alkyl group, and a number of R's is 2 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where R is an alkyl group, and a number of R's is 1 to 5)
(where A1 and A2 are represented by Formula 8)
(where R is an alkyl group or another substituent, and a number of R's is 1 to 5).
