Compounds Having Semiconducting Properties and Related Compositions and Devices
Disclosed are new compounds having semiconducting properties. Such compounds can be processed in solution-phase at a temperature of less than about 50° C. into thin film semiconductors that exhibit high carrier mobility and/or good current modulation characteristics.
1 - 24 . (canceled)
25 . A compound having formula I:
wherein:
X is selected from S, O, and CH═CH;
Y is selected from S, O, and CH═CH;
Z is H or CHR 1 R 1 ′;
R′, R 1 ′, R 2 , and R 2 ′ independently are selected from a linear C 1-40 alkyl group, a linear C 2-40 alkenyl group, and a linear C 1-40 haloalkyl group; and
m, at each occurrence, independently is selected from 0, 1, 2, 3, and 4.
26 . The compound of claim 25 , wherein the compound has the formula II:
wherein Z, R 2 , R 2 ′, and m are as defined in claim 25 .
27 . The compound of claim 25 , wherein the compound has the formula III:
wherein Z, R 2 , R 2 ′, and m are as defined in claim 25 .
28 . The compound of claim 25 , wherein the compound has the formula IV:
wherein Z, R 2 , R 2 ′, and m are as defined in claim 25 .
29 . The compound of claim 25 , wherein Z is CHR 1 R 1 ′, and each m independently is selected from 1, 2, and 3.
30 . The compound of claim 29 , wherein R 1 and R 2 independently are selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group; and R 1 ′ and R 2 ′ independently are selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 .
31 . The compound of claim 25 , wherein the compound has the formula IIa, IIIa, or IVa:
wherein R 1 and R 2 independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
32 . The compound of claim 25 , wherein the compound has the formula IIb, IIIb, IVb, IIc, IIIc, or IVc:
wherein R 1 and R 2 independently are selected from C 2 H 5 , n-C 3 H 7 , n-C 4 H 9 , n-C 5 H 11 , n-C 6 H 13 , n-C 7 H 15 , n-C 8 H 17 , n-C 9 H 19 , n-C 10 H 21 , n-C 11 H 23 , and n-C 12 H 25 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
33 . The compound of claim 25 , wherein the compound has the formula V, VI, or VII:
wherein R 2 is selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group; R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
34 . The compound of claim 25 , wherein the compound has the formula Va, VIa, VIIa, Vb, VIb, or VIIb:
wherein R 2 is selected from a linear C 3-40 alkyl group, a linear C 3-40 alkenyl group, and a linear C 3-40 haloalkyl group; R 2 ′ is selected from CH 3 , CF 3 , C 2 H 5 , CH 2 CF 3 , CF 2 CH 3 , and C 2 F 5 ; and m 1 and m 2 independently are selected from 0, 1, and 2.
35 . A thin film semiconductor comprising a compound of claim 25 .
36 . An electronic device, an optical device, or an optoelectronic device comprising the thin film semiconductor of claim 35 .
37 . A field effect transistor device comprising a source electrode, a drain electrode, a gate electrode, and the thin film semiconductor of claim 35 in contact with a dielectric material.
38 . The field effect transistor device of claim 37 , wherein the field effect transistor has a structure selected from top-gate bottom-contact structure, bottom-gate top-contact structure, top-gate top-contact structure, and bottom-gate bottom-contact structure.
39 . The field effect transistor device of claim 37 , wherein the dielectric material comprises an organic dielectric material.
40 . The field effect transistor device of claim 37 , wherein the dielectric material comprises an inorganic dielectric material or a hybrid organic/inorganic dielectric material.
41 . A light emitting transistor device comprising a source electrode, a drain electrode, a gate electrode, a dielectric material, and a photoactive component comprising a compound of claim 25 , wherein the photoactive component is in contact with the dielectric material.
42 . The light emitting transistor device of claim 41 , wherein the photoactive component comprises a laminate of two or more layers.
43 . The light emitting transistor device of claim 42 , wherein the laminate comprises a light emitting layer and one or more organic charge transport layers.
44 . The light emitting transistor device of claim 41 , wherein the compound of claim 25 is present in a blend material.