# US 8,785,915 B2 · Compound for organic thin film transistor and organic thin film transistor using the same

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- Number: US 8,785,915 B2
- Document ID: US8785915B2
- Status: Granted
- Kind: B2
- Application number: 13/060,780
- Filed: 2009-08-28
- Published: 2011-09-01
- Granted: 2014-07-22
- Earliest claimed: 2008-08-29
- Assignees: Idemitsu Kosan Co., Ltd.
- Applicants: Yuki Nakano; Masatoshi Saito; Hiroaki Nakamura; Hirofumi Kondo
- Inventors: Yuki Nakano; Masatoshi Saito; Hiroaki Nakamura; Hirofumi Kondo
- Web page: https://patentgrep.com/patent/US8785915B2

## CPC

- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- C07C 15/20: Polycyclic condensed hydrocarbons
- C07C 22/08: containing fluorine
- C07C 25/22: with condensed rings
- C07C 43/20: having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07C 255/52: to carbon atoms of six-membered aromatic rings being part of condensed ring systems
- C07C 317/14: having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
- C07C 321/28: Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07D 207/06: with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 495/04: Ortho-condensed systems
- C07F 7/0805: {comprising only Si, C or H atoms}
- C07F 7/0807: {comprising Si as a ring atom}
- C07F 7/0812: {comprising a heterocyclic ring}
- C07F 7/0814: {said ring is substituted at a C ring atom by Si}
- H10K 85/624: {containing six or more rings}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C07C 2603/24: Anthracenes; Hydrogenated anthracenes
- C07C 2603/54: containing more than five condensed rings
- H10K 10/464: {Lateral top-gate IGFETs comprising only a single gate}
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 85/731: {Liquid crystalline materials}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

A compound for an organic thin film transistor represented by the following formula (1): wherein at least one pair of adjacent two groups of R1, R3, R5 and R7 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 3 to 60 carbon atoms, the ring being fused to the ring to which the groups are bonded; and at least one pair of adjacent two groups of R2, R4, R6 and R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 3 to 60 carbon atoms, the ring being fused to the ring to which the groups are bonded.

## Claims

### Claim 1

A compound, which is one of formulas (4) to (7):
wherein each X is independently O, S or N—Z and
wherein R41 to R44 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 2 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, wherein the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group,
wherein each R41 to R44 are optionally substituted, and
wherein the compound wherein all of R41 to R44 are hydrogen is excluded;
wherein each X is independently O, S or N—Z and
wherein R51 to R54 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 2 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group,
wherein each R51 to R54 are optionally substituted, and
wherein the compound wherein all of R51 to R54 are hydrogen is excluded;
wherein each X is independently O, S or N—Z and
wherein R61 to R64 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group,
wherein each of R61 to R64 are optionally substituted;
wherein each X is independently O, S or N—Z and
wherein R71 to R74 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group,
wherein each of R71 to R74 are optionally substituted.

### Claim 2 (depends on 1)

A material for an organic thin film transistor which comprises the compound according to claim 1.

### Claim 3 (depends on 1)

An organic thin film transistor comprising:
a substrate,
three terminals of a gate electrode, a source electrode and a drain electrode,
an insulator layer and an organic semiconductor layer being provided on the substrate, source-drain current is controllable by applying a voltage to the gate electrode,
the organic semiconductor layer comprising the compound according to claim 1.

### Claim 4 (depends on 3)

The organic thin film transistor according to claim 3 which is capable of emitting light by utilizing current flowing between the source electrode and the drain electrode and the light emission is controlled by applying a voltage to the gate electrode.

### Claim 5 (depends on 4)

The organic thin film transistor according to claim 4, wherein one of the source electrode and the drain electrode comprises a substance having a work function of 4.2 eV or more and the other of the source electrode and the drain electrode comprises a substance having a work function of 4.3 eV or less.

### Claim 6 (depends on 3)

The organic thin film transistor according to claim 3 which further comprises a buffer layer between the source and drain electrodes and the organic semiconductor layer.

### Claim 7 (depends on 3)

An apparatus comprising the organic thin film transistor according to claim 3.

### Claim 8 (depends on 1)

The compound of claim 1 which is of formula (4).

### Claim 9 (depends on 1)

The compound of claim 1 which is of formula (5).

### Claim 10 (depends on 1)

The compound of claim 1 which is of formula (6).

### Claim 11 (depends on 1)

The compound of claim 1 which is of formula (7).

### Claim 12

A compound which is one of formulas (4) to (7)
wherein each X is independently O, S or N—Z and
wherein R41 to R44 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 2 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, wherein the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group, and
wherein the compound wherein all of R41 to R44 are hydrogen is excluded;
wherein each X is independently O, S or N—Z and
wherein R51 to R54 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 2 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group, and
wherein the compound wherein all of R51 to R54 are hydrogen is excluded;
wherein each X is independently O, S or N—Z and
wherein R61 to R64 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group;
wherein each X is independently O, S or N—Z and
wherein R71 to R74 and Z are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, a haloalkoxyl group having 1 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, a haloalkylthio group having 1 to 30 carbon atoms, an alkylamino group having 1 to 30 carbon atoms, a dialkylamino group having 2 to 60 carbon atoms, the alkyl groups are optionally combined with each other to form a ring structure containing the nitrogen atom, an alkylsulfonyl group having 1 to 30 carbon atoms, a haloalkylsulfonyl group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 60 carbon atoms, an aromatic heterocyclic group having 3 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an alkylsilylacetylene group having 5 to 60 carbon atoms or a cyano group.