Perylene-Based Semiconductors

Patent metadata

Field	Value
Publication number	US-2016240789-A1
Application number	US-201615043956-A
Country	US
Kind code	A1
Filing date	Feb 15, 2016
Priority date	Feb 13, 2015
Publication date	Aug 18, 2016
Grant date	—

Abstract

The present invention relates to new semiconductor materials prepared from perylene-based compounds. Such compounds can exhibit high carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

First claim

What is claimed is:

1 . A compound having formula:

wherein:
W 1 and W 2 independently are selected from the group consisting of —(CR a R b ) m —, —(SiR c R d )—, and Ar;
X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 independently are selected from the group consisting of H, halogen, CN, and OR e , provided at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is not H;
Ar is a divalent aryl or heteroaryl group selected from the group consisting of phenyl, thienyl, and furyl;
R a and R b independently are selected from the group consisting of H, a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 1-20 haloalkyl group;
R e and R d independently are selected from the group consisting of H, a C 1-20 alkyl group, and a C 1-20 haloalkyl group;
R e is selected from the group consisting of H, a C 1-20 alkyl group, a C 2-20 alkenyl group, and a C 1-20 haloalkyl group;
R 1 , R 1′ , R 2 , and R 2′ independently are selected from the group consisting of H, a linear C 1-40 alkyl group, a linear C 2-40 alkenyl group, and a linear C 1-40 haloalkyl group; and
m is 0, 1, 2, 3, or 4.

2 . The compound of claim 1 , wherein the compound has the formula:

wherein n′ is 2, 4, 6 or 8; and R 1 , R 1′ , R 2 , R 2′ , W 1 , and W 2 are as defined in claim 1 .

3 . The compound of claim 1 , wherein the compound has the formula:

wherein two of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 8 are CN, and the other six of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are H.

4 . The compound of claim 3 , wherein X 2 and X 4 are CN, and X 1 , X 3 , X 5 , X 6 , X 7 , and X 8 are H.

5 . The compound of claim 3 , wherein X 6 and X 8 are CN, and X 1 , X 2 , X 3 , X 4 , and X 7 are H.

6 . The compound of claim 3 , wherein X 1 and X 3 are CN, and X 2 , X 4 , X 5 , X 6 , and X 8 are H.

7 . The compound of claim 3 , wherein X 5 and X 7 are CN, and X 1 , X 2 , X 3 , X 4 , and X 8 are H.

8 . The compound of claim 3 , wherein X 5 and X 8 are CN, and X 1 , X 2 , X 3 , X 4 , and X 7 are H.

9 . The compound of claim 1 , wherein the compound is represented by a formula selected from the group consisting of:

10 . The compound of claim 1 , wherein R 1 is different from R 1′ , and R 2 is different from R 2 .

11 . The compound of claim 1 , wherein R 1′ and R 2′ are selected from the group consisting of a linear C 1-6 alkyl group, a linear C 2-6 alkenyl group, and a linear C 1-6 haloalkyl group; and R 1 and R 2 are selected from the group consisting of a linear C 3-40 alkyl group, a linear C 4-40 alkenyl group, and a linear C 3-40 haloalkyl group.

12 . The compound of claim 1 , wherein R 1′ and R 2′ are selected from the group consisting of CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and R 1 and R 2 are selected from the group consisting of a linear C 3-20 alkyl group, a linear C 4-20 alkenyl group, and a linear C 3-20 haloalkyl group.

13 . A thin film semiconductor comprising a compound of claim 1 .

14 . A composite comprising a substrate and the thin film semiconductor of claim 13 deposited on the substrate.

15 . An electronic device, an optical device, or an optoelectronic device comprising the thin film semiconductor of claim 13 .

16 . The device of claim 15 configured as a field effect transistor device comprising a source electrode, a drain electrode, a gate electrode, and the thin film semiconductor of claim 13 in contact with a dielectric material.

17 . The device of claim 16 , wherein the field effect transistor has a structure selected from the group consisting of a top-gate bottom-contact structure, a bottom-gate top-contact structure, a top-gate top-contact structure, and a bottom-gate bottom-contact structure.

18 . The device of claim 16 , wherein the dielectric material comprises an organic dielectric material.

19 . The device of claim 16 , wherein the dielectric material comprises an inorganic dielectric material or a hybrid organic/inorganic dielectric material.

20 . An optoelectronic device for producing an image, the optoelectronic device comprising a plurality of field effect transistors interconnected to each other and deposited on a substrate, such field effect transistors each comprising a thin film semiconductor comprising a compound of claim 1 , a source electrode, a drain electrode, a gate electrode, and a dielectric material.

Assignees

• Polyera Corp

Inventors

• Facchetti Antonio
• Denti Mitchell

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/621

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• C07D487/06 Primary

  Peri-condensed systems · CPC title

• H01L51/0558

  Electricity · mapped topic

• H01L51/0053 Primary

  Electricity · mapped topic