# US 7,745,821 B2 · Aryl dicarboxylic acid diimidazole-based compounds as n-type semiconductor materials for thin film transistors > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,745,821 B2 - Document ID: US7745821B2 - Status: Granted - Kind: B2 - Application number: 11/748,622 - Filed: 2007-05-15 - Published: 2008-11-20 - Granted: 2010-06-29 - Earliest claimed: 2007-05-15 - Assignees: Eastman Kodak Company - Inventors: Shiying Zheng; Deepak Shukla; Diane C. Freeman - Web page: https://patentgrep.com/patent/US7745821B2 ## CPC - C09B 5/62: Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series - H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide} - C09B 57/08: Naphthalimide dyes; Phthalimide dyes - H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate} - H10K 10/484: {characterised by the channel regions} - Y02E 10/549: Organic PV cells - 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 ## Abstract A thin film transistor comprises a layer of organic semiconductor material comprising an organic semiconductor material that comprises an aryl dicarboxylic acid diimidazole-based compound. Such transistors can further comprise spaced apart first and second contact means or electrodes in contact with said material. Further disclosed is a process for fabricating ac thin film transistor device, preferably by sublimation or solution-phase deposition onto a substrate, wherein the substrate temperature is no more than 150° C. ## Claims ### Claim 1 An article comprising, in a thin film transistor, a thin film of organic semiconductor material that comprises one or more aryl dicarboxylic diimidazole-based compounds selected from the group consisting of compounds represented by the following structures: wherein Ar1 and Ar2 are the same or different, and are each carbocyclic or heterocyclic aromatic ring systems, comprising 4 to 60 carbon atoms, fused to each corresponding adjacent imidazole in the structure, wherein each of Ar1, and Ar2 are substituted with at least one or more fluorine atoms, and X is an optional organic or inorganic substituent group at any available position on the core nucleus; n is zero or an integer from 1 to 8 and m is zero or an integer from 1 to 4, wherein the thin film transistor further comprises first and second contact means in spaced apart contact with the thin film and third contact means spaced apart from the organic semiconductor material. ### Claim 2 (depends on 1) The article of claim 1 wherein the thin film transistor is a field effect transistor comprising an insulating layer, wherein the third contact means is a gate electrode adapted for controlling, by means of a voltage applied to the third contact means a current between the first and second contact means through said layer, the first and second contact means are a source electrode and a drain electrode, and wherein the insulating layer, the gate electrode, the thin film of organic semiconductor material, the source electrode, and the drain electrode are in any sequence as long as the gate electrode and the film of organic semiconductor material both contact the insulating layer, and the source electrode and the drain electrode both contact the thin film of the organic semiconductor material. ### Claim 3 (depends on 1) The article of claim 1, wherein the Ar1 and Ar2 moieties are single rings or fused aromatic polycyclic ring systems, including carbocyclic, heterocyclic, or hybrid ring systems in which a carbocylic ring is fused to a carbocyclic ring. ### Claim 4 (depends on 1) The article of claim 1, wherein the organic semiconductor material is at least one compound selected from the group consisting of compounds represented by the following structures: ### Claim 5 (depends on 4) The article of claim 4 wherein X is independently cyano or fluorine or any combinations thereof. ### Claim 6 (depends on 1) The article of claim 1 wherein X is independently selected from alkyl groups, alkenyl groups, alkoxy groups, halogens, cyano, substituted or unsubstituted aryl and arylalkyl groups. ### Claim 7 (depends on 1) The article of claim 1 wherein the Ar1 and Ar2 moieties each independently comprise one or more further substituents, on one or both rings, selected from alkyl groups, alkenyl groups, alkoxy groups, cyano, and substituted or unsubstituted aryl and arylalkyl groups. ### Claim 8 (depends on 1) The article of claim 1 wherein the Ar1 and Ar2 moieties each independently comprise two or more fluorines substituted on each of the Ar1 and Ar2 moieties. ### Claim 9 (depends on 1) The article of claim 1 wherein the Ar1 and Ar2 moieties each independently comprise a benzene, naphthalene, thiophene, quinoline or pyridine ring system each substituted with one or more fluorines. ### Claim 10 (depends on 1) The article of claim 1 wherein the organic semiconducting material is capable of exhibiting electron mobility greater than 0.05 cm2/Vs. ### Claim 11 (depends on 1) The article of claim 1, wherein the thin film transistor has an on/off ratio of a source/drain current of at least 103. ### Claim 12 (depends on 1) The article of claim 1, wherein said first, second and third contact means comprise, respectively, source, drain, and gate electrodes, each independently comprising a material selected from doped silicon, metal, and a conducting polymer. ### Claim 13 (depends on 1) An electronic device selected from the group consisting of integrated circuits, active-matrix display, and solar cells comprising a multiplicity of thin film transistors according to claim 1. ### Claim 14 (depends on 13) The electronic device of claim 13 wherein the multiplicity of the thin film transistors is on a non-participating support that is flexible.