# US 7,608,679 B2 · Acene-thiophene copolymers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,679 B2 - Document ID: US7608679B2 - Status: Granted - Kind: B2 - Application number: 11/278,222 - Filed: 2006-03-31 - Published: 2007-10-04 - Granted: 2009-10-27 - Earliest claimed: 2006-03-31 - Assignees: 3M Innovative Properties Company - Inventors: Peiwang Zhu; Tzu-Chen Lee; Dennis E. Vogel; Christopher P. Gerlach - Web page: https://patentgrep.com/patent/US7608679B2 ## CPC - H10K 85/151: {Copolymers} - C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring} - H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof} - C08G 2261/124: alternating - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/314: Condensed aromatic systems, e.g. perylene, anthracene or pyrene - C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract Acene-thiophene copolymers are provided that can be used as semiconductor materials in electronic devices. The acene-thiophene copolymers are of Formula I. In Formula I, Ac is a radical of an acene having 2 to 5 fused aromatic rings. The acene can be unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof. Divalent group Q is selected from Formula III where each R1 and R2 group is independently selected from hydrogen, alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof. The subscript n in Formula I is an integer equal to at least 4. The asterisks in Formula I indicate the location of attachment to another group such as another repeat unit of formula —Ac-Q-. ## Claims ### Claim 1 A copolymer of Formula I wherein Ac is a radical of an acene having 2 to 5 fused aromatic rings, wherein Ac is unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof; Q is a divalent group of Formula III; R1 and R2 are each independently selected from hydrogen, alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, or alkenyl the asterisks indicate the location of attachment to another group such as another repeat unit of formula —Ac-Q-; and n is an integer greater than or equal to 4, wherein the compound of Formula I is a semiconductor material. ### Claim 2 (depends on 1) The copolymer of claim 1, wherein Ac is selected from naphthalene-2,6-diyl, naphthalene-2,7-diyl, anthracene-2,6-diyl, anthracene-2,7-diyl, anthracene-9,10-diyl, tetracene-2 ,8-diyl, tetracene-2-9-diyl, pentacene-2,9-diyl, pentacene-2,10-diyl, or pentacene-6,13-diyl, the Ac being unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof. ### Claim 3 (depends on 1) The copolymer of claim 1, wherein Ac is selected from naphthalene-2,6-diyl, anthracene-2,6-diyl, tetracene-2,8-diyl, or pentacene-2,9-diyl, the Ac being unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or a combination thereof. ### Claim 4 (depends on 1) The copolymer of claim 1, wherein Ac is anthracene-2,6-diyl that is unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof. ### Claim 5 (depends on 1) The copolymer of claim 1, wherein at least one of the R1 group, R2 group, or the Ac substituent has at least 4 carbon atoms. ### Claim 6 (depends on 1) The copolymer of claim 1, wherein R1 is hydrogen or has at least 4 carbon atoms and R2 has at least 4 carbon atoms. ### Claim 7 (depends on 1) The copolymer of claim 1, wherein both R1 and R2 have at least 4 carbon atoms. ### Claim 8 (depends on 1) The copolymer of claim 1, wherein both R1 and R2 are hydrogen or have less than 4 carbon atoms and the Ac substituent has at least 4 carbon atoms. ### Claim 9 (depends on 1) The copolymer of claim 1, wherein at least one of R1 or R2 is an alkyl having at least 4 carbon atoms, an alkoxy having at least 4 carbon atoms, a thioalkyl having at least 4 carbon atoms, an aryl having at least 6 carbon atoms, an aralkyl having at least 10 carbon atoms, a haloalkyl having at least 4 carbon atoms, a hydroxyalkyl having at least 4 carbon atoms, a heteroalkyl having at least 4 carbon atoms, an alkenyl having at least 4 carbon atoms, or a combination thereof. ### Claim 10 (depends on 1) The copolymer of claim 1, wherein both R1 and R2 are independently selected from alkyl having at least 4 carbon atoms, an alkoxy having at least 4 carbon atoms, a thioalkyl having at least 4 carbon atoms, an aryl having at least 6 carbon atoms, an aralkyl having at least 10 carbon atoms, a haloalkyl having at least 4 carbon atoms, a hydroxyalkyl having at least 4 carbon atoms, a heteroalkyl having at least 4 carbon atoms, an alkenyl having at least 4 carbon atoms, or a combination thereof. ### Claim 11 (depends on 1) The copolymer of claim 1, wherein both R1 and R2 are independently an alkyl having at least 4 carbon atoms. ### Claim 12 (depends on 1) The copolymer of claim 1, wherein R1 and R2 are each independently hydrogen or an alkyl. ### Claim 13 (depends on 1) The copolymer of claim 1, wherein R1 and R2 are each hydrogen and Ac is anthracene-2,6-diyl that is unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof. ### Claim 14 A composition comprising a solvent and a compound of Formula I wherein Ac is a radical of an acene having 2 to 5 fused aromatic rings, the acene being unsubstituted or substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or a combination thereof Q is a divalent group selected from a group of Formula III; R1 and R2 are each independently selected from hydrogen, alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, or alkenyl the asterisks indicate the location of attachment to another group such as another repeat unit of formula —Ac-Q-; and n is an integer greater than or equal to 4, wherein the compound of Formula I is a semiconductor material. ### Claim 15 (depends on 14) The composition of claim 14, wherein at least one of R1, R2, or the Ac substituent has at least 4 carbon atoms. ### Claim 16 (depends on 14) The composition of claim 14, wherein R1 is hydrogen or has less than 4 carbon atoms and R2 has at least 4 carbon atoms. ### Claim 17 (depends on 14) The composition of claim 14, wherein both R1 and R2 have at least 4 carbon atoms. ### Claim 18 (depends on 14) The composition of claim 14, wherein both R1 and R2 are hydrogen or have less than 4 carbon atoms and the Ac substituent has at least 4 carbon atoms. ### Claim 19 (depends on 14) The composition of claim 14, wherein at least two of R1, R2, and the Ac substituent have at least 4 carbon atoms. ### Claim 20 (depends on 14) The composition of claim 14, wherein the composition is a solution comprising at least 0.05 weight percent of the compound of Formula I based on the weight of the solution.