# US 9,518,224 B2 · Organic semiconductor particulate material, organic semiconductor thin-film, dispersion liquid for forming organic semiconductor film, method for producing organic semiconductor thin-film, and organic thin-film transistor

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- Number: US 9,518,224 B2
- Document ID: US9518224B2
- Status: Granted
- Kind: B2
- Application number: 13/819,636
- Filed: 2011-08-17
- Published: 2013-06-20
- Granted: 2016-12-13
- Earliest claimed: 2010-08-29
- Assignees: Shinshu University; Dainichiseika Color & Chemicals Mfg. Co., Ltd.
- Applicants: Musubu Ichikawa; Hyeon-Gu Jeon; Naomi Oguma; Naoki Hirata; Hisao Kono
- Inventors: Musubu Ichikawa; Hyeon-Gu Jeon; Naomi Oguma; Naoki Hirata; Hisao Kono
- Web page: https://patentgrep.com/patent/US9518224B2

## CPC

- C09K 19/3483: {the heterocyclic ring being a non-aromatic ring}
- C07D 471/04: Ortho-condensed systems
- C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C09K 19/3488: {the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines}
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- H10K 85/731: {Liquid crystalline materials}
- H10K 10/484: {characterised by the channel regions}
- H10K 10/486: {the channel region comprising two or more active layers, e.g. forming pn heterojunctions}
- Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.]
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Provided are a fine-particulate organic semiconductor material, a thin organic semiconductor film and an organic transistor. The fine-particulate organic semiconductor material is in a form of fine particles and is usable as an organic semiconductor material. The fine particles are fine thermotropic liquid crystal particles that undergo a phase transition into a liquid crystal state when heated to a temperature of from 50° C. to 350° C. The fine-particulate organic semiconductor material can easily and uniformly form the thin organic semiconductor film over a large area by a film printing process or a dispersion coating process. The thin organic semiconductor film has high electron mobility and high ON/OFF value.

## Claims

### Claim 1

A dispersion for forming an organic semiconductor film, which is useful in forming the organic semiconductor film, the dispersion comprising:
an organic solvent comprising an aprotic polar solvent having a specific inductive capacity of from 30-60; and
a fine-particulate organic semiconductor material dispersed in the organic solvent,
wherein the fine-particulate organic semiconductor material is in a form of fine particles and is usable as an organic semiconductor material, the fine particles are fine thermotropic liquid crystal particles that undergo a phase transition into a liquid crystal state when heated to a temperature of from 50° C. to 350° C., and the fine particles comprise a perylene tetracarboxylic diimide derivative,
wherein the perylene tetracarboxylic diimide derivative is N,N′-ditridecyl perylene tetracarboxylic diimide represented by the following structural formula (1):
or N,N′-bis(3-(n-dodecyloxy)-n-propyl)-3,4,9,10-perylene tetracarboxylic diimide represented by the following structural formula (2):

### Claim 2 (depends on 1)

A process for producing a thin organic semiconductor film, which comprises coating and drying the dispersion according to claim 1 on a substrate, and then subjecting a resultant coating film to heat treatment at a temperature of from 50° C. to 350° C. such that the fine-particulate organic semiconductor material in the film are allowed to undergo a phase transition into a liquid crystal state to form a uniform thin organic semiconductor film on the substrate.

### Claim 3 (depends on 2)

An organic thin-film transistor provided with a substrate and at least a gate electrode, gate insulating layer, thin organic semiconductor film, source electrode and drain electrode formed on the substrate, wherein the thin organic semiconductor film is formed by the process according to claim 2.

### Claim 4 (depends on 1)

The dispersion according to claim 1, wherein the phase transition into the liquid crystal state takes place at a temperature of from 100° C. to 250° C.

### Claim 5 (depends on 1)

The dispersion according to claim 1, wherein the fine particles have an average particle size of from 10 nm to 10 μm.