Back to results
US 8,329,855 B2Granted
Thienocoronene-imide semiconducting compounds and polymers
AssigneesPolyera Corporation, BASF SE
InventorsHakan Usta, Zhihua Chen, Antonio Facchetti
Life of this patent
Estimating the term…
Abstract
Disclosed are new semiconductor materials prepared from thienocoronene-imide-based small molecule and/or polymeric 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.
Claims17
A polymer comprising identical or different repeating units having the formula:
- or both,
- wherein:
- R1 and R2 independently are selected from H, a C1-40 alkyl group, a C2-40 alkenyl group, a C1-40 haloalkyl group, -L′-Cy1, -L′-Cy1-L′-Cy2, -L′-Cy1-L′-Cy2—Cy2, -L′-Cy1—Cy1, -L′-Cy1—Cy1-L′-Cy2, -L′-Cy1—Cy1-L′-Cy2—Cy2, -L′-Cy1-L-R, -L′-Cy1-L′-Cy2-L-R, -L′-Cy1-L′-Cy2—Cy2-L-R, -L′-Cy1—Cy1-L-R, and -L′-Cy1—Cy1-L′-Cy2-L-R,
- wherein:
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group optionally is substituted with 1-10 substituents independently selected from a halogen,
- —CN, NO2, OH, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)—C1-40 alkyl, —C(O)OH, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —OC1-40 alkyl, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), and —Si(C1-40 alkyl)3;
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group can be bonded covalently to the imide nitrogen atom via an optional linker;
- R is selected from a C1-40 alkyl group, a C2-40 alkenyl group, and a C1-40 haloalkyl group, each of which optionally is substituted with 1-10 substituents independently selected from a halogen, —CN, NO2, OH, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)—C1-40 alkyl, —C(O)OH, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —OC1-40 alkyl, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), and —Si(C1-40 alkyl)3;
- Cy1 and Cy2 independently are selected from a C6-14 aryl group, a 5-14 membered heteroaryl group, a C3-14 cycloalkyl group, and a 3-14 membered cycloheteroalkyl group, each of which optionally is substituted with 1-5 substituents independently selected from a halogen, —CN, oxo, ═C(CN)2, a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 haloalkyl group;
- L is a covalent bond or a linker selected from —Y—O—Y—, —Y—[S(O)w]—Y—, —Y—C(O)—Y—, —Y—[NRcC(O)]—Y—, —Y—[C(O)NRc]—, —Y—NRc—Y—, and —Y—[SiRc2]—Y—;
- L′, at each occurrence, independently is a covalent bond or a linker selected from —Y—O—Y—, —Y—[S(O)w]—Y—, —Y—C(O)—Y—, —Y—[NRcC(O)]—Y—, —Y—[C(O)NRc]—, —Y—NRc—Y—, —Y—[SiRc2]—Y—, a divalent C1-40 alkyl group, a divalent C2-40 alkenyl group, and a divalent C1-40 haloalkyl group,
- wherein:
- Y, at each occurrence, independently is selected from a divalent C1-40 alkyl group, divalent C2-40 alkenyl group, a divalent C1-40 haloalkyl group, and a covalent bond;
- Rc is selected from H, a C1-6 alkyl group, a C6-14 aryl group, and a —C1-6 alkyl-C6-14 aryl group;
- and
- w is 0, 1, or 2;
- wherein the polymer has a degree of polymerization (n) that is greater than 2.
14 more elements
A copolymer represented by the formula:
- wherein:
- M1 has the formula:
- M2 has a formula selected from:
- wherein:
- R1 and R2 independently are selected from a C1-40 alkyl group, a C2-40 alkenyl group, and a C1-40 haloalkyl group, wherein:
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group optionally is substituted with 1-10 substituents independently selected from a halogen, —CN, NO2, OH, —NH2, —NH(C1-40 alkyl), —N(C1-40 alkyl)2, —S(O)2OH, —CHO, —C(O)—C1-40 alkyl, —C(O)OH, —C(O)—OC1-40 alkyl, —C(O)NH2, —C(O)NH—C1-40 alkyl, —C(O)N(C1-40 alkyl)2, —OC1-40 alkyl, —SiH3, —SiH(C1-40 alkyl)2, —SiH2(C1-40 alkyl), and —Si(C1-40 alkyl)3;
- and
- each of the C1-40 alkyl group, the C2-40 alkenyl group, and the C1-40 haloalkyl group can be bonded covalently to the imide nitrogen atom via an optional linker;
- π-2, at each occurrence, independently is an optionally substituted fused ring moiety;
- Ar, at each occurrence, independently is an optionally substituted monocyclic moiety;
- Z, at each occurrence, independently is a conjugated linear linker;
- m, at each occurrence, is 1, 2, 3, 4, 5 or 6;
- m′ and m″, at each occurrence, independently are 0, 1, 2, 3, 4, 5 or 6;
- n is an integer in the range of 2 to 10,000;
- and
- x and y represent the molar fraction of M1 and the molar fraction of M2, respectively.
13 more elements
A polymer selected from:
- wherein n is an integer in the range of 2 to 10,000.
Dependencies are inferred from the claim text.