초록

Acene-thiophene copolymers with attached silylethynyl groups are provided that can be used in electronic devices. The copolymers are often soluble in common organic solvents and can be part of a coating composition.

대표청구항 ▼

We claim: 1. A copolymer of Formula I wherein Ac is a radical of an acene having 2 to 5 fused benzene rings, wherein Ac can be optionally substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations

We claim: 1. A copolymer of Formula I wherein Ac is a radical of an acene having 2 to 5 fused benzene rings, wherein Ac can be optionally substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof; Ra is each independently selected from hydrogen, alkyl, alkoxy, alkenyl, aryl, heteroaryl, aralkyl, heteroaralkyl, heteroalkyl, or hydroxyalkyl; Q is a divalent group of Formula II, III, IV, or V; R1 and R2 are each independently selected from hydrogen, alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, or alkenyl; and n is an integer greater than or equal to 4. 2. The copolymer of claim 1, wherein Ac is a radical of an acene selected from naphthalene, anthracene, or pentacene. 3. The copolymer of claim 1, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 1,4-bis(silylethynyl)naphthalene-2,7-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,7-diyl, 2,6-bis(silylethynyl)anthracene-9,10-diyl, 2,7-bis(silylethynyl)anthracene-9,10-diyl, 6,13-bis(silylethynyl)pentacene-2,9-diyl, 6,13-bis(silylethynyl)pentacene-2,10-diyl, 2,9-bis(silylethynyl)pentacene-6,13-diyl, or 2,10-bis(silylethynyl)pentacene-6,13-diyl. 4. The copolymer of claim 3, wherein the divalent group of formula —Ac(E)2— is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, or 6,13-bis(silylethynyl)pentacene-2,9-diyl. 5. The copolymer of claim 1, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(trialkylsilylethynyl)naphthalene-2,6-diyl, 1,4-bis(trialkylsilylethynyl)naphthalene-2,7-diyl, 9,10-bis(trialkylsilylethynyl)anthracene-2,6-diyl, 9,10-bis(trialkylsilylethynyl)anthracene-2,7-diyl, 2,6-bis(trialkylsilylethynyl)anthracene-9,10-diyl, 2,7-bis(trialkylsilylethynyl)anthracene-9,10-diyl, 6,13-bis(trialkylsilylethynyl)pentacene-2,9-diyl, 6,13-bis(trialkylsilylethynyl)pentacene-2,10-diyl, 2,9-bis(trialkylsilylethynyl)pentacene-6,13-diyl, or 2,10-bis(trialkylsilylethynyl)pentacene-6,13-diyl. 6. The copolymer of claim 2, wherein Ra is an alkyl having up to 10 carbon atoms. 7. The copolymer of claim 2, wherein Q is Formula II 8. The copolymer of claim 7, wherein at least one of R1 and 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. 9. The copolymer of claim 7, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, or 6,13-bis(silylethynyl)pentacene-2,9-diyl. 10. The copolymer of claim 2, wherein Q is of Formula III or IV 11. The copolymer of claim 10, wherein at least one of R1 and 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. 12. The copolymer of claim 10, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, or 6,13-bis(silylethynyl)pentacene-2,9-diyl. 13. The copolymer of claim 2, wherein Q is of Formula V 14. The copolymer of claim 13, wherein at least one of R1 and 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. 15. The copolymer of claim 13, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, or 6,13-bis(silylethynyl)pentacene-2,9-diyl. 16. A composition comprising a solvent and a copolymer of Formula I wherein Ac is a radical of an acene having 2 to 5 fused benzene rings, wherein Ac can be optionally substituted with a substituent selected from an alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, alkenyl, or combinations thereof; Ra is each independently selected from hydrogen, alkyl, alkoxy, alkenyl, aryl, heteroaryl, aralkyl, heteroaralkyl, heteroalkyl, or hydroxyalkyl; Q is a divalent group of Formula II, III, IV, or V; R1 and R2 are each independently selected from hydrogen, alkyl, alkoxy, thioalkyl, aryl, aralkyl, halo, haloalkyl, hydroxyalkyl, heteroalkyl, or alkenyl; and n is an integer greater than or equal to 4. 17. The composition of claim 16, wherein Ac is a radical of an acene selected from naphthalene, anthracene, or pentacene. 18. The composition of claim 16, wherein a divalent group of formula —Ac(E)2— where each E equal to a silylethynyl group of formula —C≡C—Si(Ra)3 is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 1,4-bis(silylethynyl)naphthalene-2,7-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,7-diyl, 2,6-bis(silylethynyl)anthracene-9,10-diyl, 2,7-bis(silylethynyl)anthracene-9,10-diyl, 6,13-bis(silylethynyl)pentacene-2,9-diyl, 6,13-bis(silylethynyl)pentacene-2,10-diyl, 2,9-bis(silylethynyl)pentacene-6,13-diyl, or 2,10-bis(silylethynyl)pentacene-6,13-diyl. 19. The composition of claim 18, wherein the divalent group of formula —Ac(E)2— is selected from 1,4-bis(silylethynyl)naphthalene-2,6-diyl, 9,10-bis(silylethynyl)anthracene-2,6-diyl, or 6,13-bis(silylethynyl)pentacene-2,9-diyl. 20. The composition of claim 17, wherein Ra is alkyl having up to 10 carbon atoms.